Biking Home

It takes me around 5 hours to drive the 295 miles between our home in Minneapolis and our cottage outside of Watersmeet, Michigan.  I’ve driven the route countless times.  It’s a chore.

The Drive

For years I’ve thought about making the trip in a different way.  In a way that would turn that chore into a lasting memory. 

On my bicycle. 

This summer I finally did it.  On Sunday, July 5th, as my family was packing up to head home after vacation, I waved goodbye and pedaled up the driveway on my loaded bicycle.*  A bucket list trip was becoming reality.

Four days and 344 miles later, I rolled up my driveway in Minneapolis at around 9:45pm. Hot, exhausted and happy. It was a moment of pure joy that eludes most adults in their 50’s like me.

I almost chickened out.  I’ve ridden a lot of miles on my bike, but my experience with self-contained bicycle touring—unsupported—is very limited.  I did a three-day self-contained trip a few years ago with friends, but never a solo trip of this magnitude.  As I packed up my bike panniers with gear, water and food, negative thoughts raced through my head.  “I’m not in the greatest biking shape.  What if I have a mechanical issue I can’t fix?  Where am I even going to camp tonight?”  Sometimes, it’s little things that push us forward.  In this case, it was a little patch embroidered on the inside sleeve of the t-shirt I was wearing.  It reads, “Day One or One Day?”  I was sick of saying “one day.”  Today would be Day One.  I’m so glad I was wearing that shirt.  The things that make us nervous, that push us, often result in the experiences that make a life well lived.

Day One

Choosing the best route home was easy.  There is an organization called Adventure Cycling Association that publishes a network of bicycling routes that crisscross the country.  And as luck would have it, their “North Lakes” route passes a few miles south of our cottage on its way to Minneapolis.  The set of maps, which included turn by turn directions and identified grocery stores, restaurants and campgrounds, were a massive help.  It would have been a far more difficult trip without them.    

Adventure Cycling Association Map

For several reasons, I needed to travel the 344 miles in four days—leaving on Sunday afternoon and sleeping in my bed in Minneapolis by Wednesday night.  That’s 86 miles a day.  As I settled into a strong pace my first twenty miles or so, the distance felt attainable.  It was a very hot day, and I stopped a few times to dunk my head into one of the many beautiful lakes I passed. 

Then the sky darkened.  And I noticed that the cars coming towards me from the west had their lights on.  Not a good sign.  A few minutes later the storm hit.  The next town, Boulder Junction, was about 8 miles away.  I took shelter under a big oak tree and ate an energy bar, hoping it would pass quickly.  It didn’t.  My tree started to lose all of its water shedding properties.  I realized that I was basically standing there in the rain, so I hopped back on my bike and rode into Boulder Junction, where I found a park shelter to hide under while I assessed the state of my gear.  The day was slipping away and I wasn’t yet sure where to camp for the night. 

Around 7:15pm, 56 miles in, I limped into a public campground on Big Lake, outside Manitowish Waters.  Although soggy, I took a nice swim after setting up camp and enjoyed ramen noodles while a full moon rose.  Not bad.  I did regret bringing a very small sleeping pad, as my tent site was gravel.  But I fell asleep without effort.   

Day One – 56 Miles

Day Two—No Wolves

The bumper sticker posted on the tavern door said “No Wolves.”  I like wolves.  They embody wildness and make the forest feel alive and complete—a fully functioning system rather than a game farm.  

If I was driving my car I would have turned around.  I don’t want to support or interact with No Wolves folks.  But I was on my bike.  And Day 2 of my trip was about to include another huge storm. 

The morning started out great.  I biked through the forest on a paved trail outside of Mercer, Wisconsin, as the sun sliced through the mist.  Fully caffeinated after a breakfast over my camp stove, I felt alive and completely engaged in the present moment.  The miles flew by.  A few hours in, as the humid July heat cranked up, I stopped at a store for Ibuprofen, two bananas and a Gatorade.  If my bike shorts didn’t give away my mode of travel that day, my purchase surely did. 

Breakfast of Champions

Not long after that stop, on a long stretch of straight highway west of Turtle Flambeau Flowage, I noticed huge storms bubbling up on the western horizon.  The storm closed rapidly, and the wind turned suddenly cold against my sweaty skin.  With no structures in sight, I started looking for trees with water shedding properties again. “But aren’t tall trees and lightning good friends?”, my mind interjected.  And just then, the Midway Bar appeared out of nowhere.


I tucked my bike into an open shed around the side of the tavern and hustled for the front door.  After a moment’s hesitation, I went in; my desire to seek shelter from the impending deluge trumping that No Wolves greeting on the door.

I’m glad I did.  The couple running the bar were gracious, letting me hang out until the storm had passed and offering to top up my water bottles while my bike sat in their shed and my phone powered up along the wall.  I enjoyed my lunch conversation with the owner behind the bar, even though I didn’t agree with everything he said.  As I biked away after the storm passed, it struck me how easy it is to avoid interacting with people with whom we disagree.  It’s a shame, because I’m never going to change someone’s mind or better understand their perspective that way.  By categorizing them and dismissing them before I even say hello.  My guess is that the bar owner probably would have avoided me too, especially in my smelly bike clothes, but I hope we both left the conversation with a little better understanding of the other.  It wouldn’t have happened if I had been safely ensconced in my car, barreling home in a hurry. 

That’s part of the beauty of bike travel—it kicks us out of the isolated bubble in which many of us reside.  On a bike, you become a traveler in the oldest sense of the word.  You are vulnerable and may need to rely on the kindness of strangers, especially if you are new to self-supported cycling, like I am.  And for some wonderful reason, pedaling a bicycle is disarming—most folks view you as a curiosity rather than a potential threat.  As a result, opportunities to have positive interactions with people abound. A ride can restore your faith in humanity, or at least give you a needed dose of empathy.  

Back on the bike, I started to consider where to camp that night.  It was hard to plan ahead of time, because I wasn’t sure how far I’d make it each day.  This uncertainty caused daily anxiety, but it also made the trip flow in a serendipitous way.  Day two ended that way.  After deciding to push past camping options around Clam Lake, I found a sweet little private campground on Ghost Lake outside of the Hayward area vacation megalopolis.  The camp owners didn’t answer their phone, but eventually I roused them and they pointed me to an empty field of campsites up the hill and showed me a building where I could take a nice hot shower.  Because of Covid, their restaurant was shut down, but I saw another food option on the Adventure Cycling map just down the road called Ghost Lake Lodge. 

Approaching Clam Lake, WI

After setting up camp and taking a dip in the lake and a hot shower, I headed over to the Lodge, a beautiful old log cabin surrounded by a ring of guest cabins strung out along the lake shore.  It was hard to climb back onto my bike after 88 miles that day—my rear end was not happy—but it was worth the trip.  I found the Lodge empty, and waited at the bar for someone to appear for 10 minutes or so.  The owners, an older couple, eventually appeared.  They were a delight.  The husband poured himself an old fashioned, something I could tell he had done many times.  And the wife set about to getting me a beer, and then a pizza.  Their kindness had a genuine, grandparent like nature to it.  But as I sat out on the back deck watching the sun drop with a nice buzz and a full belly, the grumble of thunder broke in, again.  The radar on my phone confirmed that another big storm had come calling. 

As I hustled out the door to race back to my camp that was not ready for rain, the wife thanked me and told me that she would leave the lodge door open overnight, and that I was welcome to sleep inside if the storms got really bad.  Yet another example of the magic interactions that happen when you are on a bike. 

Day Two – 88 Miles

Day Three—Making Up the Miles

It was a rough start to the day.  My body was not happy that I was contemplating getting back onto a bicycle, especially the parts that made contact with my bike seat.  Swapping out my shorts on day two had quite literally rubbed me the wrong way.  Even after a pot of coffee and a lot of oatmeal cooked up on my camp stove, I could tell it was going to be a hard start.  And I had a lot of miles to make if I was going to be sleeping in my bed come Wednesday night.

Thankfully the energy returned to my body quickly once I rolled out of the campground around 9:15am.  It might have been in part because of the beauty around me.  A winding forest road.  Mist rising again from the damp pavement in the morning sun.  Stream crossings and the sound of rapids.  A few deer, a brood of turkeys and ravens cawing from the woods.  I took a deep breath and again felt so alive, and so lucky to be out here pedaling under my own power and feeling my body getting stronger.  Every place except my butt, which was threatening to end the trip early. 

As I rolled into the Hayward lakes area, the traffic picked up in volume and speed.  The Adventure Cycling route was fantastic, but Hayward was my least favorite part.  Especially as I cycled the narrow road around the Casino on the Lac Courte Oreille Indian Reservation, I found myself wondering whether the driver of the car about to overtake me was paying attention to me or their phone.  I switched on my red blinking tail light, which always gives me a bit more comfort.

On day three the diversity of the Wisconsin landscape was on full display.  I went by farm fields, deep forests, lake shores, and small towns, again and again.  And I noticed all of it, every hill, every road surface, every change in the land, at my 14mph pace.  Another steamy July day, I enjoyed a few stops to dunk my head in a lake or take a quick swim. 

The day’s lunch stop was at the Chit Chat tavern in Edgewater, Wisconsin.  The tavern was for sale.  The owner/bartender had not had a day off in over two months, but you couldn’t tell it.  My Coca-Cola and fish sandwich basket cost $9.15.  I’m guessing there is not a lot of money to be made at the Chit Chat, but I’d recommend a stop. 

Emerging from the dark, air-conditioned confines of the Chit Chat felt like entering a tropical rain forest.  I love heat and humidity, but I could tell this mid-day heat was nothing to take lightly.  I stopped at a little market in the tiny town (the only store) and bought two bananas, two Gatorades and a jar of Vaseline.  All of them helped immensely. 

I’ve done a lot of endurance type exercise, but it still amazes me how important food becomes to your body’s ability to carry on.  I pulled into Edgewater dragging and worrying about whether I could make enough miles for the day, and I pedaled out feeling strong.  But the heat was oppressive and the long open stretches around Haugen tested me.  One stretch in particular is etched in my mind.  It was a long straight country road without a tree in sight.  Miles in the distance a huge hill rose up, waiting for me.  That hill sucked, especially when a diesel pick up truck passed me and put his accelerator to the floor to welcome me to the neighborhood.

Reaching Haugen felt like an accomplishment.  I popped into a little village market that felt like a scene from the 1950’s, complete with a tin ceiling, checker floor and tiny shelves.  There was a wonderful, old couple running the place.  The Greatest Generation.  She was stocking.  He was behind the ancient cash register.  I think they would still be talking to me if I had stayed to continue the conversation.  Sadly, he struggled to make change from the $50 bill I gave him.  I immediately felt bad for calling out the miscalculation, as I could tell he was disappointed in himself.  I wish I would have just considered it a tip to them and what appeared to be many, many years of hard work in that little store that used to be a bigger part of the community.  It was a bittersweet moment to see a disappearing glimpse of the past, and I turned it over in my head for many miles.  I hope they are still there when I do this trip again.   

A few more strategic head dunks in lakes and a few more Gatorades later, I made it all the way into Cumberland, Wisconsin, and found a beautiful little public campground on a peninsula jutting out into the lake right in the middle of town.  I was the only tent, again.  I bought a couple of beers at a bar downtown and a sub sandwich and sat on the lake shore by my tent watching the sun set.  There were loons calling and an osprey fishing.  Serendipity.  After Facetime calls to my Mom and Dad and Sarah, I turned in.  95 miles in the bag.  It was a great day. I just might make it to Minneapolis tomorrow after all. 

Day Three – 95 Miles

Day Four—Minivans and Heat Indexes 

What the hell is that guy doing?” I thought.  I was on my second attempt to put some distance between myself and the city of Cumberland—the first attempt earlier that morning resulted in my retreat back to town to hide under an awning on Cumberland’s main street from another huge, angry storm.  I’m used to cars flying by me, but in this case, I was gaining ground on a very old mini-van that was loaded with crap, hoarder style.  The person driving said vehicle was creeping along around 10 mph in the left-hand lane of a two-lane highway with only the driver side tires slightly off the road.  As I gained ground, the van started to climb up a very large hill—anyone coming over that hill from the opposite direction would meet this van head on.  This was fast becoming a life or death scenario.  Do I pedal like hell and catch up?  Fall back and avoid being part of the carnage?  I tried to catch up, but the car crested the hill before I did, and quickly took a right across the road and down a driveway.  As I passed by, I think I saw a flat tire on the driver’s side.  This idiot was driving on the opposite shoulder to save a tire rim.  You blindly trust a lot of drivers when you are biking, so seeing this kind of calculus—I’ll save my tire rim and avoid having to get out of my car in exchange for the risk of a violent death—was not comforting.  A few minutes later, a couple in a green pickup truck passed me.  I saw the detail of their faces and thought about how lucky they were that morning that they hadn’t driven past a few minutes earlier.  It’s easy to forget how fragile and seemingly random life can be. 

The day got much better.  After I passed the big storm and Mr. Minivan, the winds shifted around to provide a very strong tailwind.  The first noticeable tailwind of the trip.  The wind pushed me and my wide panniers along the open country road and I powered up to my biggest gear.  The speed became almost effortless.  It was a gift on what I knew was going to be a very long and hot day.  I’m pretty sure I might have spontaneously yelled “yes!” a few times on that stretch of road.  When was the last time you shouted out in joy?  Another example of the wonders of biking. 

The speed induced joy didn’t last.  The effects of the storm moved on, the wind shifted back around, and the sun returned to deliver the heat index warnings that were forecast.  I started to search the map for lakes and temporary relief.  But instead of heatstroke, I discovered something else on day four—our human bodies are amazing.  We can beat them up, push them to failure, exhaust our reserves, but they eventually respond.  I had pushed through the dead legs and sore butt of the first few days and now my body was starting to toughen up.  My legs felt strong and capable.  Blisters turned to callouses.  What a blessing it is to push yourself and find enough toughness to meet the challenge.  What a feeling!  Those moments provide a whiff of invincibility and confidence that I have used to plug into so many other parts of my life.  And you can too.  I’m not a great athlete or a natural on the bike—my calves are so skinny that my family makes fun of them.  But on day four, I felt strong and the well inside of me felt deep.  The dance between mind and body that plays out in endurance activities has been life changing for me.    

Strong legs or not, it was hot.  The hottest day of July, in fact.  I stopped at few gas stations to slug Gatorade in the icy AC, and the miles ticked by.  I had over 100 to make, and as I reached the St. Croix river valley and the border into Minnesota, I became confident that, heat or not, I would finish the trip that day. 

Maybe I got a little too confident, because not long after the cycling gods brought me back to reality with my only crash of the trip.  I was biking through a highway underpass tunnel that had stagnant, standing water on the far end of it.  I hit the water, and in an instant the slimy pavement turned as slippery as ice and I was down in a heap, struggling to unclip and crawl out from under my bike.  Thankfully the damage was cosmetic, and off I went, with the benefit of having soaked half my shorts and shirt in stinky, but cooling, water.

Crossing Highway 35 south of St. Croix Falls, I started my descent into the river valley on, you guessed it, River Road.  It was the greatest segment of the trip.  Starting on a ridge line high above the river, I felt like I was dropping into a ski run.  With big descents and sweeping turns, the road winds beautifully through the forest and seems to go on forever.  It was shaded, it was cool, it was exhilarating.  If it was an amusement park ride, I would have paid to do it again, and again.  But it wasn’t a ride, and all of that descent had to be clawed back in less than a mile on the other side of the Hwy 243 bridge into Minnesota.    

The invincibility I felt earlier in the day was fading, but crossing into Minnesota helped.  Especially after I reached the town of Scandia and joined up with a route I’ve done on long weekend rides.  I was back on home territory and no longer needed a map.  Thankfully, this home stretch was made easier when my friend Pat Dockry joined me to bike the last 25 miles or so to my house.  Pat provided a huge mental lift and it was great to have him along. 

And then it was almost over.  We crossed the Mississippi River as the sun set over the city.  I couldn’t stop smiling.  In the darkness I rolled onto my street and then into my driveway; Sarah and the dogs were outside waiting for us.  107 miles.  A state of joyful exhaustion washed over me.  A feeling you can’t get without a lot of hard effort.    

Day Four – 107 Miles

After pizza, beer and a shower, I lay in my bed that night drifting off to sleep.  In my mind’s eye, I rolled back across the distance I had covered the past four days, envisioning the roads and towns, lakes and forests, and fields and farms in between here and there in a completely new way.  The opportunity to earn that distance under my own power, and really experience it on a human scale and at a human pace was a gift.  Unlike my car trips, I’ll never forget it. 

I can’t wait to do it again next year. 

*Thanks for reading. I’d love to to answer any questions you may have about the route, gear, bike or other logistics.          

Posted in Adventure | Tagged , , | 8 Comments

The Startup Maze

I recently gave a talk at UW-Madison.  The presentation–part of WARF’s Entrepreneurons Series–was about entrepreneurship generally, and more specifically, about what it’s like to think up, launch and scale a start up.  It’s something I’ve done four times, and I really enjoy drawing lessons from the success and failure I’ve had along the way.

Start-ups are hard.  As founders, we need all of the support and help we can get.  I hope some of the personal lessons I highlight in this talk will help those of you that are in the start-up maze right now.  And I hope my experience helps encourage more of you to make the leap.

Here’s the video:


Screen Shot 2016-06-22 at 1.48.30 PM





Posted in Entrepreneurship, Start-Ups, Uncategorized | 4 Comments

Find the Experts-How to use Podcasts & Curated Lists to get Smarter/Faster/Better

In my last post announcing my EIR role at American Family Ventures, I mentioned how much I value working shoulder to shoulder with smart people.


Today, I want to highlight another method to surround yourself with brilliant people that can teach you, inspire you and drive you, even if you don’t have the opportunity to work directly with these experts in your day job. And it’s (mostly) free.

Push and Pull, Push and Pull

Google has put the world of information at our fingertips, but it’s also made us complacent. Don’t know the answer to something? No worries, just Google it. Or ask Siri. And sure, it’s amazing that the answer to any question is a few milliseconds away, but there is a huge limitation to this method—it assumes that you know the right question to ask. You also need to think about what information can be pushed to you. It’s the other side of the pull coin. And it’s neglected by far too many people once they leave their traditional school education behind.*

Your Very Own Panel of Experts

What I’ve found is that it’s pretty easy to assemble your own customized panel of experts, thought-leaders and super smart people in almost any field. And, once assembled, this panel of experts will supply you with a daily dose of wisdom, no strings attached.

Let me repeat: A continuous push of thought provoking, inspiring, and insightful content is waiting out there for you—it’s pretty incredible when you think about. And the fact that most of it is free means that you’re an idiot if you don’t take advantage of this great gift from the Interwebs.

My Example

By way of example, here’s a small sampling of the sources that I’ve set up to push me information. You’ll note that most of this is related to technology, entrepreneurship and business innovation, but you can find similar experts in almost any field of interest (say Meditation, or Sailing, for example).

Curated Emails & Lists.  It amazes me how many people and organizations will now hand pick the best information out there on any subject for free. Here is my cherished group of curators.

Jason Hirschhorn’s @TechREDEF. REDEF curates daily mixes of information around a number of themes. The Tech mix (tech + innovation + culture) is simply outstanding. I receive a daily email newsletter of these mixes and they never disappoint.

Mattermark Daily. A fantastic daily email, “The Mattermark Daily is a hand-curated newsletter compiled daily to bring you first-person accounts of entrepreneurship, investment and insights from the startup ecosystem.” I especially love Mattermark’s selection of insights from operators (e.g., those in the trenches starting companies).

StrictlyVC.  The Silicon Valley editor of TechCrunch produces this daily curated email that tracks recent company fundings and other important news in the Venture Capital space. She calls herself “your very own venture capital concierge.” I agree.

Jitha So it Goes. A weekly newsletter for start-ups, delivered each Saturday morning, it makes for great weekend reading.

Farnam Street Brain Food.  A weekly digest curated by Shane Parish each Sunday that explores “new posts, books I’m reading, and interesting things I find across the web on subjects like art, history, science, philosophy, psychology, and human misjudgment. It’s basically brain food.”

TechCrunch Crunch Daily. The grand-daddy of Technology and start-up news. I like the quick email summary of their most important posts of the day which keep me in the loop with minimum effort.

Vox Sentences. This daily email does a wonderful job of describing the top three to five big news items of the day in simple, clear language with links to more in-depth reporting. I read it each night before bed and it feels like my librarian friend is telling me everything important that happened that day.

Twitter—By Way of Nuzzel.  Like many, I stopped visiting Twitter on a daily basis because it can be overwhelming and time consuming. But Twitter remains THE source for timely news. Thankfully, there is now a wickedly brilliant and simple service called Nuzzel that enables you to get the best of Twitter in a daily email. Trust me, you need to sign up and use this service (even if you haven’t invested in following the right people—just pick the Nuzzel stream of someone with similar interests). I can’t believe Twitter hasn’t either copied this service or purchased it yet.  I get a daily email of my Nuzzel feed as well as the feeds from several other people that have similar interests. You can read the simple concept behind Nuzzel here.

Podcasts.  Oh how I love you Mr. Podcast. You enable me to fill the dead parts of my day, commuting, mowing the lawn, etc., with the voices of brilliant people. And you give me a break from the screen, which is an extra bonus. It appears I’m not the only one that loves me some Podcast (see here and here).

a16z. Produced by VC firm Andreessen Horowitz, these podcasts are short and cover some of the leading topics and trends that are top of mind in Silicon Valley, the epicenter of my profession.

The Tim Ferriss Show. Tim Ferriss does deep dive/long interviews of elite performers in fields as diverse as music, government, start-up investing and big wave surfing. I sometimes struggle with the “dude factor,” but Tim is a great interviewer and many of these podcasts genuinely inspire me, uncover new insights, and identify people that I now follow.

Common Sense with Dan Carlin. So much of being an entrepreneur is being contrarian. Dan Carlin is brilliantly contrarian in his take on current events, politics and society.

The Writers Almanac. I wake up my brain every day with this five minute reading by Garrison Keillor.

Exponent. I’ll say more about Ben Thompson below, but this is his weekly podcast with friend James Allworth. The podcast is a fantastic way to tap into Ben’s thought stream on technology and corporate strategy. I love it Ben, but please stop saying “fundamental” so much.

Ben  Ben Thompson is a great example of the theme of this entire post, so I’m giving him an entire category. His site,, is an embarrassment of riches for business strategy, innovation and technology. In addition to the Exponent podcast, he offers a paid Daily Update email and associated member forum (of which I subscribe, the only thing in this entire list that I pay $ to receive), and he also publishes a free weekly article. Here is Ben, at his finest, describing the Uber opportunity and developing a framework for disruptive technology. I can’t believe this information is free.

Communities.  In addition to Ben Thompson’s member forum, I’ll highly two other communities in my field of entrepreneurship—ProductHunt and Angelist.

ProductHunt is an amazing community of entrepreneurs and product makers that debate and discuss almost every newly launched technology start-up. The community provides me with insight, competitive intelligence and inspiration on a daily basis. One of my favorite features is a set of curated startup lists that any Product Hunt member can create. For example, I’m interested right now in the Invisible Web, and sure enough, ProductHunt founder Ryan Hoover keeps his own running list of Invisible Web start-ups right here. Thanks Ryan!

AngelList has essentially democratized the start-up funding process. It gives any start-up founder unprecedented access to investors, and highlights the best and most interesting start-ups, leaving you feeling very plugged in regardless of your geography. One of my favorite things is to check the Trending Startups, which AngelList is nice enough to push to me in a weekly email.

Blogs.  A lot of the content above is driven by an underlying blog to which I subscribe. Here are a few I haven’t mentioned yet that I find super valuable.  But I have to mention that lots of my attention lately has shifted towards the curated content rather than visiting my RSS reader:

AVC, by Fred Wilson.

Feld Thoughts, by Brad Feld.

Steve Blank, by-you guessed it-Steve Blank.

Essays, by Paul Graham.

Online Courses.  This post is getting too long, but I can’t neglect to mention the fact that you can use services like Coursera and others to sign up for university and graduate level courses, as well as find folks that are posting their summary of courses online (like this one I’m following from Chris McCann who is posting his notes on Reid Hoffman’s new Stanford Business School course “Technology-enabled Blitzscaling”).

So there’s my highlighted list**. If you’ve spent the time to create something similar (or better) in your field of interest, kudos to you. I hope you agree with me that it is well worth the effort.

If you haven’t, what’s stopping you?

What’s Your Excuse?

I don’t have time.  I suspect many of you are thinking that you don’t have time to assemble and digest information like this. For many of you, I’m calling B.S. The average American watches 5 hours of T.V. everyday.  Add in passive screen time for things like Facebook and I’ll bet that hourly total goes up a lot. Could you take 10% or 20% of your T.V. and leisure screen time and devote it to building your expert panel? Could you organize your day differently, say to get up 20 minutes early each day for your experts?

In my own life, I discovered that I was listening to entirely too much sports talk radio. It was like bubble gum for my brain. Once identified, I was shocked at how much time I spent listening to debates about who is going to start, get a contract extension or win the next game. I quit it cold turkey and substituted all of that time with the podcast material I highlight above. It was a fantastic trade off. Do you have a bubble gum for the brain habit that you could substitute?

I don’t know where to start.  In addition to asking friends and colleagues for recommendations and searching for a few podcasts in your interest area (see the Podcast articles I link to above), I’d start with Nuzzel. Pick anyone that shares similar interests with you and that uses Twitter regularly and follow their Nuzzel feed (for example, here is super investor Chris Sacca’s feed). It will lead you on a journey of personal development that you won’t regret.

I’ll leave you with a quote I heard Naval Ravikant, the founder of AngelList, say during a podcast interview on the Tim Ferriss show (seeing a trend here?):

“If you want to be happy, surround yourself with people who are less successful than you, but if you want to be successful, you need to surround yourself with people who are more successful than you”

There are lots of successful people out there, ready to push you. What are you waiting for?

*Still in school? Start building your daily push of experts now and you’ll have a HUGE advantage over your peers.

**If you’ve got a favorite expert or source that I haven’t mentioned, please leave them in the comments below as inspiration.

Posted in Entrepreneurship, Start-Ups | 1 Comment

Why I’m Working at an Insurance Company

I just finished a year off.

As I mentioned here (Why I’m Taking a Sabbatical), I set out to have an adventure with my family and to better answer the question “what am I on this earth to do?”  It was an incredible opportunity to step out of regular life and take a long, hard look at myself—an out of body experience. Sure it was scary to be on the sidelines and my bank account hated it, but it was one of the most valuable things I’ve ever done.

There are obvious reasons it was awesome, like precious, 100% time with my family and teaching my son. But I also learned something very valuable about myself. I learned that I love to create things—it’s what makes me come alive.

This is sort of a hard thing to realize because my creative outlets are limited by my lack of skills. I can’t paint or draw or sculpt. I can’t sing or play an instrument or compose a symphony. I can’t dance (at least not well). What does that leave? Thankfully, it leaves something I’ve already done . . .

Create Ideas.

To me, there is nothing quite as amazing as taking an idea that develop in your mind (often with people smarter than you) and help to launch that idea and see it take on a life of its own. To see it solve a problem and make a difference in peoples’ lives. Ask any grizzled entrepreneur and they will likely agree that the experience is intoxicating and will have you coming back time and time again for more.

I want to continue working in the world of ideas.

That’s why I’m excited to announce that I just started a new role as an “Entrepreneur in Residence” at American Family Ventures. It’s a great opportunity for me to support the innovation initiatives that American Family has underway, at the same time that I explore solutions to the problems that matter to me.

This is only the second time in my professional life that I’ve worked* for a company that I didn’t help start, but the decision was a no-brainer for me for several reasons.

Here’s why:

“You are the average of the five people you spend the most time with” Jim Rohn

The innovation team at American Family has some serious horsepower. I love working with people that are smarter than me. There is no better way to become better at what you do.

The phrase “Insurance Startup” is no longer an oxymoron

Timing is everything and the insurance space is reaching a tipping point. Industries with high barriers to entry because of complicated legal structures and/or high capitalization requirements used to be insulated from the Mark Zuckerbergs of the world, but one look at what is happening in markets like financial services (e.g., Lending Club) and transportation (e.g., Uber) shows that this is no longer the case. The traditional insurance incumbent moat is eroding, a fact not lost on smart incumbents. The space is wide open.**

American Family isn’t just giving lip service to being innovative

Entrepreneurship is hot right now, and almost every Fortune 500 company is talking about innovation. But a lot of it is just talk while the C-Suite continues to focus myopically on making its next quarterly number. American Family’s innovation push, in contrast, is coming from the CEO and leadership with a real mandate. They are taking the long view. And backing it up with real actions. Case in point—a company using innovation for their public window dressing wouldn’t quietly (and massively) increase the $’s allocated to their Venture Fund. But guess who did just that?

Brown Star this is not


Empathy is a super power

I’ve sat across the table from venture investors and big company biz dev and M&A folks for 15 years. I now get to sit on their side of the table—get an inside view of how they make decisions, what keeps them up at night, better understand their incentives and what their world is really like. Empathy is a hidden super power of really good entrepreneurs (a fact I’ve written about before) and this experience is going to make me a better/stronger/faster entrepreneur.

A person’s value system is the sum total of their actions. A person’s words, thoughts, decisions, promises have no value until they act upon them. Christian Hacker

I’ve done a lot of reading and thinking during my year off. I’m excited to jump back in and start making things happen again.


*I’m an independent contractor, like an Uber driver 🙂

**This is not a guarantee that I’m going to start something in the insurance space or even launch another stand alone start-up from scratch, but many of the themes being addressed in this space (consumer data, customer relationships, social risk, Aggregation theory) fascinate me.

Posted in Entrepreneurship, Start-Ups | 6 Comments

What We Can Learn from Silicon Valley

I’ll admit it. As an entrepreneur working in Wisconsin, I’m jealous of Silicon Valley.

Case in Point:

A few weeks ago, a social planning app called Free ( launched. It wasn’t much different than the dozens of other mobile apps that have tried (and failed) to solve the tricky problem of social planning. There is a high body count in this space—Klamr, Hotspot, Klutch, WeShould, WeOtta, Inviteful, Flock, WePopp—the list goes on and on. And I should know; my previous start-up Nextt is in this list of casualties.

Ffrree, in my humble opinion, hasn’t really done anything significantly better than these past start-ups. Not yet anyway.

Sure, the UI is very clean and easy to use, but do people really want to broadcast that they have nothing to do, e.g., they are “flexible?” And the service is only available on the iPhone. What about the +50% of my friends that have Android devices and are left out of the main features?

And yet, despite these drawbacks, Ffrree launched with some fanfare, including a glowingly positive TechCrunch post and a coveted spot in Apple’s Featured App section.


This is a HUGE advantage. As a start-up, it isn’t enough to build a great product. You need distribution for that product or you will fail. Even if your product is awesome. As Peter Thiel points out in Zero to One, relying on the Field of Dreams if you build it they will come strategy isn’t going to work. I talk to a lot of founders, and this is a very common mistake that I see over and over again. Focus solely on building a great product and neglect how you are going to get customers at your peril.

My first reaction to the Ffrree launch was to say WTF? It feels like these guys have an unfair advantage just because they are in Silicon Valley. Inherent distribution baked into the product by means of geography.

But this is a stupid reaction on a few levels. First, I hope Ffrree is wildly successful, as I really believe in the mission to make social software connect us more in the real world away from our screens.  Good luck Ffrree.

And more importantly, you aren’t going to learn anything with sour grapes. So I’m focusing on what I can learn from Ffrree, and Silicon Valley in general.

Here are my takeaways . . .

Packaging & Presentation Matter

There was a video that made the rounds a couple of months ago that showed the incredible power of context and packaging. In the video, a mass-produced IKEA poster was placed in a fancy Dutch art gallery. And as you might expect, lots of folks gushed over its brilliance. A crappy IKEA poster, worth millions when placed in an art gallery.

Tynan has a great post on this subject here in which he talks about how cheap wine in fancy bottles got the same glowing reaction and how a violin virtuoso who draws tears in concert halls received almost zero attention when he posed as a street musician.

I think this same bias is at play in the case of Ffrree. Compare the media reaction to Ffrree with the negative coverage that Microsoft received when it launched its own social planning app called Tossup around the same time. Did the fact that bumbling behemoth Microsoft was behind Tossup and a Silicon Valley stud cofounded Ffrree matter? Of course it did.

People Need Shortcuts

Here is the simple truth: people are busy and we all use shortcuts to navigate our jobs and our lives. We apply rules to save time.

And if you are an entrepreneur, one of the most important rules is this—no one is going to pay attention to you unless you can quickly validate your start-up. Potential investors, co-founders, employees, customers and advisors are looking for clues about whether your start-up is worth their time. Reporters too.

This is why Ffrree got such a great reception despite having a V.1 of their product that amounted to an IKEA print. It was incredibly easy for the media to validate Ffree:

  • The founders have really solid backgrounds, including leadership roles at high-powered consumer technology start-ups. Been there done that.
  • They have a really high profile roster of investors, including Google Ventures, First Round and Chris Sacca’s Lowercase Capital.
  • They probably got warm introductions from friends that are friends with the folks writing at TechCrunch and gate keeping at Apple. Stanford or YC alums likely. People vouched for them.

It makes perfect sense. I’m the gatekeeper at Apple or TechCrunch. I get flooded on a daily basis with pitches. I need rules to sort through this and figure out what is worthy of attention. With the validation above, I can easily and quickly validate Fffrree. They are worth my time and I’m certainly not sticking my neck out promoting them. The result is that Ffrree gets a crap ton of positive launch attention and the assumption that the first version of their product is just the start of something more brilliant in the pipeline.*

What Can We Do Outside of the Valley?

So what can entrepreneurs that work outside of the Valley do? Especially those of us in smaller market cities like my city of Madison, Wisconsin, that don’t enjoy the advantages of Ffrree.

Practice Empathy

Super investor Chris Sacca was interviewed on Tim Ferriss’s podcast recently. The entire interview if really great, but one of the most brilliant things that Chris highlighted in his discussion is how empathy is a secret super power of great entrepreneurs. I couldn’t agree more.

Successful entrepreneurs (and big company leaders, sales people, marketers, religious leaders, the list goes on and on) are really good at figuring out the worldview of the people they want to influence. They are able to put themselves into the shoes of the customer, the investor, the employee, and any other high profile target they need to capture. What makes her job easier? What is she afraid might happen?   What does he strive to be? What key point will motivate this person?

Put yourself in the chair of that person and ask “what’s in this for me?”

Let’s apply this concept to the goal of getting launch coverage in TechCrunch. If you can’t use the validation playbook that worked for Ffrree, what else can you figure out about that TC reporter? How can you make their job easier? How can you add value? What validation can you present that fits into the short cuts they apply and makes covering you low risk/high reward for them?

Here’s one simple idea: Maybe they are concerned about Silicon Valley bias. Maybe they realize that they write mostly about stuff in their backyard. You could pitch the opportunity to write about this concept at the same time that they mention you. It’s a way to turn your weakness (not in the Valley) into a strength (different=worthy of attention).

I’ve tried all kinds of pitches like this, and they always start with empathy for the target. Sometimes they work and sometimes they don’t. The important thing is to take your best shot with that specific target’s world view in mind—a blanket spam press release to everyone under the sun is a complete waste of time.

There are many more ways in which you should practice empathy–in particular by applying it to your potential customers—and I plan to return to this subject in a future post. But the key takeaway here is that those of us outside the Valley have to be masters of empathy to get people to pay attention to us.

Don’t Lean-Start Up

I know this view is anathema in today’s entrepreneurial community, but I think the Lean Start-up method—treating your start up like an experiment through which you “fail your way” to success through a series of rapid fire product tests—is being overused and misused by lots of entrepreneurs. A start up is more like that IKEA work of art than it is an easy A/B test.  Presentation matters.

I had a start-up pitch me last week on an advisor role. The first thing I did was check out their website and the images of the app in the App Store. And amazingly, I found numerous spelling errors in both. I applied my own short cut—these guys don’t know what they are doing. They are sloppy and overwhelmed and if they can’t do this simple thing correctly, it is highly likely that their actual product deliverable is equally shaky. I’m out.

I’m sure the founder in this case was trying to apply the Lean Start-up mantra—move fast with a very basic version of your product so you can get actually customer feedback into your organization as quickly as possible. Speed trumps presentation and packaging. And while I wholeheartedly agree with the overall goal of getting market feedback ASAP, you need to recognize that you are playing with fire here. How many customers looked at the huge spelling error on the first screen of the app store image and applied the same short cut that I used?   Is this founder really getting true market feedback with his sloppy product presentation? I doubt it.

Using Lean Start-Up takes a high degree of discipline and proper sequencing to truly separate signal from noise. You can’t just throw stuff around and expect to see what sticks.

Maybe folks with Silicon Valley connections and pedigrees can get by with sloppy v.1 product tests because they carry the Silicon Valley brand. But that playbook doesn’t work well for those of us scrapping and clawing our way past the gatekeepers and smaller pools of early adopters outside of the Valley. Presentation and packaging matter. Perception matters.

Stick Together

Brad Feld has done lots of great work on how to make a start-up community take off anywhere. He’s literally written the book on it and backed up his ideas by applying them in his town of Boulder, Colorado. One of the most important pieces of this advice—start up communities need to stick together and support each other.

Silicon Valley is great at this. They have a huge, hungry pool of early adopters ready to try new unproven things—a.k.a. eating their own dog food. Uber is a fantastic example—they launched and cut their teeth providing fancy black SUV rides to the San Fran early adopter crowd. Would folks in other start-up communities have hopped into the back of a stranger’s car with some unknown service launching in their community? Probably not.

We need to have this same early adopter spirit in our own start-up communities. I’ve been a huge offender of this rule; head down focusing on just my own work. I’m vowing here to change. I’m going to try to lend what support I can to organizations like Capital Entrepreneurs,, the newly formed Starting Block Madison, The Water Council, Gener8tor, and other local efforts to publicize and grow start-ups in my region.

One easy thing that anyone can do: I’m going to make an effort to be an early adopter for start-ups in my region that count me in in their target market.

And lastly, I’m going to encourage those of us in entrepreneurial communities outside of the Silicon Valley to think broadly about how they define their community. Bigger is better in my opinion. In my specific example, Madison and Milwaukee and the Fox Valley and Whitewater need each other to put together Brad Feld’s four required elements of a start-up community. And while we are at it, why are we stopping at our borders? Minneapolis/St. Paul and Chicago are close neighbors. What can we do to here in Wisconsin to pull in and leverage the resources they enjoy as larger markets? What can they gain from our support?

Labels matter here. Maybe we need a new label that captures and coordinates the entrepreneurship happening across our region. Minnesota recently came up with a really clever campaign to separate themselves from the stodgy Midwest label and recast themselves as “The North.”   Is there a label that can make our entrepreneurial community bigger, stronger, better?

Bottom line—it is possible to build a very successful start-up outside the Valley. But we need to realize that we don’t enjoy all of the built in advantages that their geography affords them. We can’t succeed by simply copying the market leader. We have to bring something different and unique to the table. We need a different playbook to succeed in our own neighborhood.

*Attention at launch is great—but it has to also be backed up with a great product and sustainable business model to ultimately succeed, even in the Valley. The anonymous messaging app Secret ( is a recent and classic example.

Posted in Entrepreneurship | 2 Comments

Travel School. What I Learned Homeschooling my Son for Five Months

My wife, son and I just returned from a 5-month trip. We spent most of this time sailing a boat from Grenada to the Virgin Islands. Just the three of us—it was an amazing, inspiring, awesomely fun adventure.

I had several goals for the trip, but now that it’s over, I think one of the best parts of the experience was homeschooling our son, who turned 13 on the trip. With two caveats*, I’m going to try to highlight some of the best parts of that experience, and ways in which any parent can try to achieve some of the same benefits we found without quitting a job or heading out on a sailboat.

Put another way, here is a very big question that every parent should ask: What is the best way to educate my children to maximize the chance that they will be smart, creative, curious, happy adults that make a positive impact on the world? In other words, successful.  

What School Doesn’t Teach

I read a book recently called “How Children Succeed.” In the book, the author bifurcates the skills and capabilities that education teaches our kids into cognitive and non-cognitive groupings. Our current educational system stresses the cognitive. Math skills, reading comprehension—stuff that you can practice through repetition and that can be easily measured and tested. But what about the non-cognitive? Things like persistence, self-control, curiosity, grit, self-confidence and creativity. These are much harder to teach or measure in a standardized setting, but they are highly correlated to success in the real world.  Some people call them character.

What School Teaches That You Shouldn’t Learn

I’m an entrepreneur. I’ve been able to make a great career, despite the fact that I didn’t go to school to study to be an entrepreneur or even learn about business (secret: my math skills weren’t good enough to get into business school). I learned most everything I know about my profession by jumping in and muddling through.

And although my 20 years of traditional education taught me a great deal, I actually had to unlearn a couple of things from school that would have held me back from success. I wrote about these lessons here, but the short version follows. School taught me that my teachers and professors will tell me what I need to know—I could just sit back, memorize what they taught me and wait for their graded approval. School also taught me that in order to be successful, I needed to be good at everything. This meant that I spent the majority of my time devoted to subjects in which I lacked a natural talent. Successful people in the real world do NOT follow these two lessons. In fact, they do the exact opposite. If you want more evidence of how our current educational system is creating generalist followers, this talk by Sir Ken Robinson is worth watching.

Our Travel School Challenge

Thus, we looked at the opportunity to take Jimmy out of his 7th grade classroom for a semester as a challenge. How could we best compliment his ongoing public education? How could we develop those non-cognitive skills and provide him with the best opportunity for adult success?

A Few Things We Did

I’m not an expert in education and I don’t pretend to know all of the answers. But here are a few things that we experimented with that seemed to work.

#1. We put Jimmy in charge of as much as possible.

What do you want to learn? Pick a few things that really interest you. Jimmy picked fishing. He picked learning about sharks and the other creatures that live in the Ocean and on the islands of the Caribbean. He picked investing and the stock market. And we also encouraged him to ask questions about the world around him and we would help him figure out how to answer those questions.

Hidden lesson: don’t wait for others to tell you what is important. Go out and do what interests you. Find out stuff that you have a “knack” for doing. And do more that stuff.

#2. Curiosity meet the Internet.

We have a box of old encyclopedias in the room above our garage. That’s where I was forced to go for answers when I was thirteen. Today, we have the Internet. Anything you want to learn, you can. Never in the history of the world has it been easier to follow your interests to become an expert in something.

Throughout our trip, we researched questions that came up, like tides and weather and Communism and Darwin’s Theory of Evolution. Why does Apple make so much money? Why is the Ocean blue? Why do my ears pop underwater? Those are great questions Jimmy. Let’s figure them out. And we also tried to be proactive in certain subjects rather than just reactive to specific questions. We subscribed to podcasts. Jimmy learned the ukulele from YouTube videos. We signed up for online courses on physics and computer programming. And although we didn’t get around to doing ½ of the stuff I’d hoped to accomplish (like learning to program), I think all of this demonstrated to Jimmy that there is a big, amazing world out there that he can dive into anytime he wants.

#3. Blurring the line between schoolwork and life.

Before this trip, Jimmy’s life was organized into pretty tight segments. School time, homework time, and all that other time when he didn’t have to learn anything and was free to actually have fun. We turned this upside down on our trip. Sure, we had a few set school tasks to keep Jimmy up on his cognitive skills like math, reading comprehension and writing, but we kept scheduled school time to a minimum.

Instead, we tried to weave learning into just a normal part of each day. A great example of this is something that we did for entertainment. Because we didn’t have T.V. or Internet often, I downloaded NPR’s Serial podcast on my phone for us to listen to at night after dinner. The podcast was about the trial and conviction of a teenage kid for the murder of his girlfriend and the lingering questions about his guilt or innocence. And although it entertained us as much as a good television series, it also taught Jimmy a ton about the rule of law, how our courts work, criminal law, debate, and truth and justice. But it never felt like school. This happened over and over as we simply explored the “real world” on our trip and Sarah and I talked about things the world has already taught us.

#4. Experiment with Calculated Risk Taking.

A lot of the things that I’ve achieved in life have been the result of calculated, thoughtful risk taking. I bet you can say the same. Yet why is it that in the U.S. we work so hard to completely take our kids out of managing any risk in their lives? Many of us would put our kid in a giant protective bubble if we could. I think it’s a big mistake. Kids are capable of much more than we sometimes give them credit.

We saw this first hand during our time on the Island of Dominica. Dominican kids are treated like little adults. For example, many of these kids receive a machete before they turn 10. A big, sharp machete. Yet, we didn’t see a single kid missing a finger or hand or worse from this responsibility. They step up to the responsibility and they become very confident in the process. Jimmy took a lot of calculated risks on the trip. He learned to scuba dive. He checked our anchor by himself. He swam in deep water where he couldn’t even see the bottom. We bought him a machete. We made him “captain for the day” at the end of our trip and he was in charge of sailing a 41ft, thirty ton boat from point A to point B. And each time he used his own judgment to manage a risk effectively, he got more and more confident and better able to understand a good risk from a bad one.

#5. We weren’t normal.

To be exceptional at something you must, by definition, be outside the norm. Yet, as social creatures, we feel a tremendous obligation to fit in. To go along. In most professions, just fitting in isn’t going to get you very far. And finding true happiness in life often involves having the guts to write your own script. Our trip was a bit crazy and atypical. It was really different. And not only did it show Jimmy how big the world is, I think it has also given him the permission and freedom to be different when he so chooses. To put another way, Jimmy now views being different as a positive part of his identity. I think this is a tremendous gift to give any teenager.

Empathy—An Unexpected Result

I listened to a podcast interview of Chris Sacca recently. Chris isn’t exactly a household name, but he is one of the best early stage investors on the planet and he has over a billion self-made dollars to prove it. When asked what he viewed as the most undervalued skill in an entrepreneurs skill set, he didn’t hesitate with his answer—Empathy. I couldn’t agree more. It’s hard to make any change in the world without influencing other people. And it’s impossible to influence people unless you understand their worldview. What makes them tick. What they fear and love and hope for. That’s empathy.

We didn’t explicitly set out to try to teach Jimmy empathy on our trip—it just sort of happened. Looking back it makes sense. We met people from all walks of life: All sorts of different ages, income levels, nationalities, ethnic backgrounds, and cultural backgrounds. We ate and drank with them, we worked with them, we hiked and explored with them, we played with them, and we tried to help when the opportunity presented itself. And Jimmy was like a sponge in each of these experiences, soaking up our differences, asking questions, trying to make sense of why all of us do what we do in life. My guess is that this part of our experience will be the most lasting and most impactful part of our road school experiment.

Some Stuff Didn’t Work

I don’t want to paint too rosy of a picture here. Not everything we did worked. Hardly. The best example of this is probably my efforts to instill in Jimmy the value of deferred gratification (doesn’t it feel better to play on your phone after you get some quality work done?). During the trip, we worked with Jimmy to fill out a daily and weekly “sheet of integrity” that listed the things he wanted to accomplish. He did this every week and most days, and even experimented with the format of his lists. I hoped that this would result in an epiphany—it feels better to relax and goof off when I’ve done something worthwhile first. I had visions of Jimmy at home this summer, getting up and independently setting his priorities for the day.

It hasn’t turned out that way. Left to his own devices, I’m pretty sure he would play video games and binge watch Netflix all day. Perhaps I had too high of expectations for a 13 year old. Perhaps I just need to give him the control to be a slacker for a week or two and miss accomplishing things. I’m not sure of the answer, but I wanted to point out that we don’t have one yet. All of this is a work in progress.

Wrap Up—Things you can teach without buying a sailboat or quitting your job

Parents can be divided up many different ways, but here let’s divide them into two groups: those who continually work to become better at the job of parenting, and those who do not. My guess is that any parent reading this post falls into the former camp. And I hope that I’ve inspired you and perhaps given you some new things to try in your quest to give your kid the best chance of being a success.

To that end, here are a few specific ideas.

#1. Explore life together.

Go out and do something with your kid in the real world. Sign up for a volunteer experience. Road trip to a new town for the day. Visit a museum (yawn). Get outside of your day-to-day routine together. Doing this has two huge benefits: a) it shows your child that you care about them with your actions; and, b) it enables them to learn how you navigate and understand the world. You are their most direct and impactful teacher. And if you really want to make it count, do something atypical/weird that gives your kid permission to be unique. Don’t just go to a museum, have a contest to see who can find the ugliest work of art or the most obscure collection of things. Don’t just visit a small town, see if you can find the best piece of pie in your area. Don’t drive through a city. Walk it and see what you find. You get the picture.

I just finished an inspiring book about death. That might sound impossible, but Peter Barton, the former CEO of Liberty Media pulled it off in “Not Fade Away: A Short Life Well Lived.” In the book, Peter approaches his impending death from cancer, and although this guy made gobs of money and rubbed shoulders with the rich and powerful, the thing that he seems most proud of is a series of field trips he designed and took with his kids that he called “Real World Outings.” They learned where things actually go when you flush the toilet. They learned about fast food. They visited an airport and studied luggage handling. Simple stuff, but it had a huge impact on him and his kids.   Most of us have the ability to do these things. They don’t require millions of dollars or weeks of time. Go do something together.

#2. Introduce your kid to risk.

Resist the temptation to put your child in bubble wrap. Seriously. Financial risk, bodily risk, emotional risk. Let them quit something. Buy them a lottery ticket with their piggy bank money if that’s what they want. Do something physically challenging that takes courage. Give them something that they view as dangerous. Take the coffee challenge with them. And most importantly, even if they aren’t really in control and you are supervising the whole thing, let them feel like they are making the decision to take the risk.

#3. Live in an intellectual household.  

We watched an amazing movie the other night called “The Lady in No. 6” about Alice Sommers, the oldest holocaust survivor in the world. It’s a short film and I’d highly recommend it for a number of reasons. But the one I’ll highlight here is what Alice said about her education. According to Alice, the most important form of education anyone can receive is to be brought up in an intellectual household. In fact, she credited it with setting the framework for her amazingly rich life.

Just what does that mean, an intellectual household? To me, it means that as a parent you remain relentlessly curious about the world and that you share this curiousness and what you learn with your kids. Ironically, that is what I was trying to do while watching The Lady in No. 6 with my kids. Learn more about human nature and happiness.

Here’s an easy way to get started. On your way home from work ask yourself, what did I learn today? And then share that with your kids at dinner.

One thing I’m going to do this summer—paint one of our kitchen walls with whiteboard paint. And anytime I learn something new or cool, anytime I have a question or I’m confused, I’m going to whiteboard it. And I hope I can get the rest of my family to play along too. One example: “you are the average of the five people you spend the most time with.” You don’t need a literal whiteboard, but I think the image of your family whiteboard captures what it means to live in an intellectual household. Is your whiteboard empty or full?

In closing, I’ll respond to what many of you are thinking—I don’t have the luxury of time to do all of this stuff. And some of you may not. But I’d challenge you to really think about how you spend the hours of each day. Here’s a personal example. If you are like me, you’ve probably invested a great deal in your kid’s athletic career. You’ve paid for camps. You’ve driven everywhere, even across state lines. You’ve sat on the sidelines. Hours and hours and hours of time. Don’t get me wrong, I love sports and I think they have a lot to teach kids. Athletics and exercise are a huge part of my life. But think about this time and whether you could take just a small portion of it to do some of the things you’ve come up with from this post. And then ask yourself which set of hours will have a bigger long-term impact.

Bottom line, even if everything you try fails miserably, your child will be left with the most important belief of all—that you care deeply about them and tried your best. Anything else is really just extra.



I apologize for doing a humblebrag about my own child. I couldn’t think of a way of talking about how great our travel school experience was without using specific examples of the benefits I’ve seen reflected in Jimmy.

When I criticize our educational system, I’m talking about the system and not the teachers that participate in that system, may of which are wonderful, caring and smart people that make a difference in lots of lives.

Posted in Adventure, Entrepreneurship | 3 Comments

Re-Entry—It Isn’t Just Hard On Astronauts

We are back.

Just a few short weeks ago Sarah, Jimmy and I stepped off the boat that had been our short term home and began a 22 hour journey from Tortola, B.V.I., that included a ridiculously dangerous taxi ride, a ferry ride involving the rescue of a capsized sailboat, two long flights, and a 1AM drive from Milwaukee to our home in Waunakee, WI.

The Journey Home Begins


The Last Picture of the Trip


We are back. Back to pets, unopened mail, and lawn mowing. Back to bills, budgets, expectations, responsibilities and goals. Back to friends and family. Back to feeling normal. But also feeling really abnormal, like we used to live here.

Happy Reunions 


But Missing This . . . .


Yes, re-entry has had its ups and downs. Right now, I’m working hard to distill what I’ve learned from the experience and translate it into the next phase of my life’s work.

In other words, I’m asking myself “what the hell do I do now?”

Entrepreneurship, in many ways, is about freedom. Freedom from gatekeepers and bosses. Freedom to pursue something in which you are passionate. Freedom to pick and choose opportunities. Freedom to make yourself into something that you design.

So I’m using my experience as an entrepreneur to help me address this strange freedom that comes from stepping outside of your regular life.

And one of the first lessons that keeps sticking in my head comes from this great list of from the VC Fund First Round:

Choose Must.

There is a difference between what you should do (or could do) and what you feel that you must do. Here’s how Elle Luna describes that question in the First Round piece:

Elle Luna quit her dream job at the peak of success. She left Mailbox before it was acquired by Dropbox because she wanted to create art. Over the next year, the talented designer behind Uber‘s mobile app and Medium painted, traveled to Bali, and launched her own textile venture, The Bulan Project. Most importantly, she emerged with a lesson that applies to everyone: ‘There are two paths in life: Should and Must. We arrive at this crossroads over and over again. And each time, we get to choose,’ says Luna. Should is how others want us to show up in the world — how we’re supposed to think, what we ought to say, what we should or shouldn’t do. Must is different. Must is who we are, what we believe, and what we do when we are alone with our truest, most authentic self.’ The hard thing about Must? It’s a daily practice and a recurring choice. The good news? You arrive at these crossroads again and again, and you always get to choose. Here’s how Luna did it

This “must” question isn’t easy to answer. But as I consider it, I keep reminding myself that finding satisfaction and joy and meaning from life doesn’t come from lazy things like sitting around drinking beer all day—or from hard things like selling your soul to make more money so you can buy more material possessions (or sit around drinking more expensive beer all day). That stuff just doesn’t last.

And I also remind myself that the “must” career question shouldn’t be a completely selfish one. It also has to work for my family and fit with the “must” responsibilities that I have as a husband and father.

Jeff Goins, in his new book “The Art of Work” makes this point brilliantly with the following quote from Jackie Robinson

A life isn’t significant except for its impact on other lives.

Exactly.  Here’s hoping that we can all make an impact that matters.  And that you are able to make the freedom to ask these questions too.

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New Friends & Sad Endings

Welcome back,” the Cruz Bay Customs Official said to me as I stepped up to clear into the United States on the island of St John. After the longest absence of our lives, we were back on U.S. soil. I have to confess that it felt good in a familiar sort of way. Like walking back into the family home after your first year of college. I don’t like everything that my country does, but I do love my country.

Back in the U.S.A.


After clearing in, we made a short sail back to Maho Bay, on St. John’s beautiful north shore. I say “back” because we have vacationed here many times with family and friends. In fact, it is the first place that I dipped my toe into the Caribbean Sea.

A homecoming.

Tree frogs calling from the twilight hillside—the white sand of Maho beach reflected in the thick moonlight—the “goat path” up to the now shuttered Maho Bay Camps—the spot where my girls would “lay out” in a fit of adolescence bliss and burn their already peeling winter skin in the Caribbean sun.

Places are like old songs, they bring memories pouring back.

And this place was making us miss our girls, and our family and friends. Sure, we had a blast snorkeling, relaxing and hiking at Maho and then again at anchorages in Leinster Bay and Salt Pond Bay. And sure the sailing is amazing and easy here with short distances between islands and waves that make you feel like you are on a Midwestern lake. But there was an underlying feeling of emptiness, as the echoes of past trips bounced around noisily in our ears.

Swimming with the Fishes–Salt Pond Bay


How We Felt After Reaching the Virgin Islands


It was the perfect time for Serendipity to join our trip again, this time in the form of “Buddy Boating.” If you’ve read this blog for some time, you may remember me talking about Scott and Brittany Meyers. The Meyers set out a few years ago from Chicago on a sailboat and haven’t looked back. I’ve followed the adventure that is their life on Brittany’s blog Windtraveler since the beginning. Three kids, two boats and thousands of sailing miles later—they are still going strong. We met Scott and Brittany in Chicago for dinner before our trip, searching for advice and maybe just a little bit of courage. A friendship was formed.

And now, serendipitously, we were getting the chance to see them again right here in the British Virgin Islands.

Shine-A-Light, Shine-A-Light, this is Asante, over.” I tell Jimmy to grab the VHF radio and answer Scott’s call to our boat, which he does. “This is Shine-A-Light, switch to channel 69, over.”  Jimmy is excited and so are Sarah and I. We’ve just grabbed a mooring ball in Great Harbour on Jost Van Dyke and the Meyers are there too on their boat Asante, along with their friends Eben and Genevieve on the sailboat Necesse. For the next four days, we get to experience what live aboard cruisers call “buddy boating.”

The Meyers’s Mini-Van Complete with Double Carseat 


Buddy boating is pretty much what you’d think. You learn that boat friends are in the area (usually this happens now via Facebook), you meet up, and you then bop around from island to island, from sundowner to sundowner, from dinner to dinner, from hike to hike, together.   It’s pretty loose and informal most times, and man is it fun.  Sarah and I wanted to get a glimpse on this trip of what it might be like to actually live on our own sailboat, and buddy boating is a big reason why we now have more “pros” than “cons” on our live-aboard sailor ledger.

Of course our favorable experience was due in large part to the awesomeness of our traveling companions. I’m not sure how Scott and Brittany pull it off, but they are raising three amazing girls on a 44 foot monohull sailboat. Oh, and did I mention that their oldest daughter just turned 3 and the two youngest are 13-month-old twins? Yep, their days are a constant sand-filled stream of crawling, feeding, napping, cleaning, crying, wiping, drooling, diapered, bucket laundry, sippy cup craziness. And they pull it off with a smile and an energy that is amazing.* Rock-Stars.

We spent time with our “buddies” on Jost Van Dyke, then moved with them to Cane Garden Bay, Tortola, to celebrate Brittany’s birthday, and finally sailed together around the north side of Tortola to Marina Cay. On our final morning together, Scott invited us over for waffles made with their new waffle iron. Scott was due in Road Town, Tortola that morning, but he rescheduled the meeting. As we lingered and talked long after the waffles were gone, it was pretty clear that we were all having trouble saying goodbye. In a few short days, a lasting friendship had been formed. The goodbyes were as hard as we expected, and we left with a strong feeling that this wouldn’t be the last time that we spent time with this amazing family.

I can’t wait to be a Dad someday,” Jimmy said to us after we untied our dingy from Asante that morning and made our way back to our own boat. I think that takeaway tells you the kind of people we had just started calling our good friends. And he wasn’t the only one that had gained a new perspective and some insights.

Spending time Buddy Boating made me think about how many of us wait for some future milestone—a job title or a 401k balance—before we “sail away.” Instead, we put in our time doing something that we don’t really love in the hopes that someday we can [fill in the blank].

Is waiting wrong? That’s a personal choice obviously, that bleeds into questions about what it means to live a full and rich life that matters to you and the people around you. These are questions I have pondered often on this trip and the crews of Asante and Necesse provided me with a different perspective. A perspective that will certainly help me as we wind up our adventure and return to our “real” lives.

Someday I’ll [fill in the blank]. It’s a question all of us should ask of ourselves. I hope you are able to design a life for yourself that makes it really hard to answer that question.

Jimmy & Isla


A Day in the Neighborhood


Waffle Party


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Into the Dark

I think I just saw an old colonial woman out there,” Sarah said to Jimmy and me as she rejoined us at the helm. Having not seen the movie Bridesmaids, I didn’t immediately get the joke, but quickly realized that I didn’t need to worry about a sea rescue. “Wow, is it dark out here . . .

Up until now, Sarah, Jimmy and I have been able to do our island hopping during daylight hours. It’s been pretty easy—you point your boat at the next island after breakfast and usually arrive in time for lunch. But the Anegada gap, a stretch of open ocean about 90 nautical miles wide between Anguilla and the British Virgin Islands, forces a change in that routine. Assuming a safe average of 5 knots/hour, the trip across from Anguilla takes around 18 hours. Yep, we need to do this one in the dark.

Night passage. In the sailors’ learning curve, this is a biggie. We spent the day bumming around Road Town, Anguilla, all of us a bit anxious for our 6pm departure. Batteries in headlamps? Check. BVI waypoint entered in GPS? Check. Harness out and jacklines rigged in case we need to leave the helm? Check. Lifejackets out? Check.

Bumming Around Anguillla


At 5pm, Jimmy and I grabbed take out pizza from town and Sarah got the boat ready and set up our sleeping arrangements in the salon for the night. I planned to stay up most of the night, but Sarah and Jimmy each wanted to do their own shift at the helm too. We decided that the other two would sleep in the main salon, within earshot of the helm in case something came up.


We pulled up anchor around 6pm and started to make our way off shore. For a rookie, coastal sailor, pulling anchor at sunset is a strange and exciting feeling. Here we go. Into the dark. We quickly got our sails set on a broad reach and made some distance from the shoreline and its myriad fish nets, lobster pots, and other obstacles. We watched the sun set, and the stars slowly emerge. And then it got dark. And because there was no moon, it got really dark.

Getting Underway


It takes a long time for your eyes to adjust to darkness, and all of that hard-earned night vision can be ruined with one flash from a bright light. Because of this, we kept all of the lights off in the boat with the exception of our running lights at the top of the mast. The result was a feeling of charging headlong into the darkness, waves and unknown.

Eyes Closed for Night Vision


Night changes everything. It is sort of like walking in the woods. Take a walk down your favorite path in the daylight and everything is relaxing and beautiful. But do that same walk in the pitch black of night and it’s a whole different ballgame. Every sound, every rolling wave, every big puff of wind felt a bit ominous at the start.   Thus, the old colonial woman. But as the hours went by, we started to get more comfortable and trust in the boat and each other.

The conditions didn’t hurt our growing confidence either. We picked a great night, with winds in the 10 to 15 knot range right behind us. It was a gentle ride down the waves, for which we were very thankful. Other than having to dodge a big tanker and a few other boats, the night was blissfully uneventful. And amazingly beautiful. We watched our boat wake light up with bioluminescence as we disturbed thousands of tiny organisms that fired off light in the water. It felt like we had giant sparklers attached to both hulls. Or like a whole new universe of stars had taken up residence below the water to mirror the Milky Way above us. Mesmerizing.

The three of us sat there at the helm together, on and off for most of the night. Our own little self-sufficient world. The stars whirled overhead, the waves rolled, the earth spun, and we tumbled forward into the unknown together. It was a microcosm of this trip.

The sunrise saw Jimmy and me at the helm, still offshore and out of sight of land. I was taking over for him after his 4am shift and he wanted to watch the sun come up with me. I was so proud of him. When I left him at the helm at 4 and went to bed, it struck me that this was the very first time in my life that I fully, 100% trusted him to take on a very adult responsibility. Jimmy’s got this, I thought to myself as I fell asleep. And he did. It’s amazing what young people can accomplish when given the responsibility. It’s something I’ve learned on this trip and want to take back with me.

Blue Grey Sunrise


Back to Sleep


Sarah got up a bit after Jimmy went back to sleep and we made coffee and fired up the engines to gain a little speed as we were still several hours from dropping anchor (yep, it was that calm). What can I say about Sarah? This is a woman who was terrified of the open ocean just a few short years ago. And now here she was, sitting next to me completely at ease and loving the moment. Sure, she had her bear spray ready last night in case we had “marauders” by the boat, but she was enjoying this moment and the feeling accomplishment. I felt so thankful that she trusted me to do this trip. There are many ways to be rich in this world, but I think that being in love with your spouse has to rank up there as the most important kind of wealth. That the light in her smile, the way she smells, and her warm hug makes me feel much the same way it did when I met her over 25 years ago. What a blessing.

Coffee at Sea


We (finally) grabbed a mooring ball in the Bight on Norman Island around 1pm. A very slow and very amazing 19 hours at sea. We had passed our test and had taken a big step on our way to becoming sailors. And we now get to enjoy the calm waters of the Virgin Islands. I’ve flown here from the U.S. many times, but this arrival felt much different. It was earned together with my family. Is there a better way to travel?

Our Path Across the Anegada Gap

Screen Shot 2015-05-06 at 9.26.50 AM

We Made It!  




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Up Island

Traveling the Caribbean by sailboat is something that I’ve dreamed about for years.  And I can now confirm that the actual experience is even better than I expected.  After saying goodbye to our college girls, Sarah, Jimmy and I departed Antigua and started heading “up island,” as they say around here.  We hit Montserrat, Nevis, St. Barths and Anguilla.  And we made our first overnight passage together from Anguilla to the U.S. Virgin Islands, a distance of about 90 nautical miles.  It hasn’t sucked.

Making Landfall

Arriving in a new country by sail is pure awesomeness.  You leave one country and the next one comes slowly into view over your bow.  Details start to emerge.  Roof tops come into focus, individual trees stand out, and before you know it you are dropping anchor with a sense of anticipation to explore a completely new place.  This kind of travel–slow, peaceful (most of the time), and completely on your own schedule–is really unique.  Each time we leave an island, I think about my last step as I push off from shore in the dingy and realize that my next footfall will be on a new beach in a new country later that day.  No airports, no lines, no TSA, no luggage.  Just the three of us in our temporary floating home.  It’s an amazing way to travel, even if you do have to shower outside and manually flush your toilet.

Hello Statia, It’s Nice to Meet You


Customs, Immigration and Port Authority

And o.k., I have to admit that our travel isn’t completely without some bureaucratic hassle.  I do have to clear in and out of each country we visit.  This involves a visit to 3 separate government offices, which are usually located right next to each other and are overstaffed and chock full of procedures that will make the DMV feel like  Checking out of Antigua was representative.  I first went to Customs, but they told me to go first to Immigration, then back to them, then to Port Authority and then finally back to Customs one final time.  The offices were all in the same building the size of a large garden shed.  Yep, I’m not making that up.  You just have to smile.  And so far (knock on wood) the process has been quick and painless.  If you wear a shirt with a collar, shower occasionally, and show the officials respect, things seem to go quite well.

I Miss the DMV


Daily Adventures

My cousin Jennifer McGuire commented on a picture I posted online that she loved following our daily adventures.  That phrase has really stuck with me.  It captures perfectly what this trip feels like.  Each day has involved a new adventure (or three).  These adventures have been possible because we have put ourselves outside of our comfort zone.  We aren’t on a tour, or following the directions of a hotel concierge, or tour guide, or cruise ship.*  We are completely “winging it” as they say.  But getting outside of our comfort zone has opened up some amazing experiences. Some are uncomfortable and a bit scary (I’m not the best sailor in the world), some are funny, and some have brought a complete sense of wonder.  But all of them have been authentic, real experiences that make me feel like I’ve lived 4 regular years of my life in the past 4 months.  I wish I could always feel this way.

The following are a few highlights.

The Montserrat Volcano

Montserrat is a beautiful little island that reminded us of Dominica.  It’s people are friendly and the island is lush and green.  Lots of famous musicians have recorded music here, including Paul McCartney, The Police and The Rolling Stones.  But unfortunately, in 1997, the Soufriere Hills volcano decided to wake up.  It destroyed the main town of Plymouth and several outlying towns in a series of eruptions that have spanned several years, the most recent of which was in 2010.  The residents that remained, about 5,000, had to relocate to the unsettled northern part of the island.  They literally had to pick up one weekend and move everything–government offices, the prison, the bank, churches, you name it.  It’s pretty incredible to think about.  We did a 4-hour volcano tour with a guy named Joe Phillips who lost his home (and home town) in the eruptions.  He was full of knowledge and pictures showing us first hand the before and after as he drove us into the wasteland.  Other than Joe reminding us about 4,000 times how great his tour was and how hard he worked on it, it was an incredible experience.  We got to feel geologic time in real time, and see how most of these islands were formed.  Surreal, awesome, sad, up lifting.  It confirmed that what we build is not permanent.

A House that was a Home


No Time to Even Grab Clothes


Yes, That Was a Swimming Pool


Monkeys on a Morning Hike

We all loved the island of Nevis.  It has a sort of proper old English feel to it, it’s clean and mostly uninhabited, and the huge cone volcano made us feel like we were in Hawaii or the South Pacific somewhere.  We stayed two full days here, visiting museums (Jimmy’s favorite, not), the town market, and a bunch of ruins and historical sites.  My favorite experience though, was on the morning of our departure.  Sarah and I got up at dawn and did a hike up the mountain to the ruins of the Pinney Estate.  We saw the remains of an old Caribbean cook house, the largest baobab tree I’ve encountered, and a troop of monkeys.   I’d love to spend more time here someday.

A Much Friendlier Volcano


The Cook House


Waz Sup Monkey?


Quill Volcano

Our next stop was the Dutch island of Statia.  We had an “interesting” sail from Nevis, meeting winds that went from 2 knots to +35 knot winds in the blink of an eye as we rounded St. Kitts.  It was the first time that Jimmy and I really worked as a team to get the boat under control.  I wanted him to have a few scary moments like this on the trip to grow his confidence and he handled it better than I did.  13 year olds are invincible.

Statia is a land of commerce.  It was a free port for 100’s of years, providing sailing ships a tax free way to move goods around the Caribbean and to the U.S. and Europe.  It was the place that many enslaved Africans first stepped foot in the Caribbean.  And it is still a bustling, busy port, only now they distribute oil through here rather than enslaved people and sugar.  Even though we had a giant tugboat for our backdoor neighbor and we rolled around the anchorage at night like a carnival ride, we loved this place.  The old town and fort have been remarkably restored, the slave road into town is impressive to say the least, and the hike up into the huge Quill volcano crater made me feel like I had been dropped into the t.v. show Lost.

Hello Neighbor


The Quill Volcano Crater-Our Goal for the Day


Mission Accomplished


Sharks Under the Boat

Jimmy has discovered that if he floats our blow up solar light off the back of the boat at night, creatures emerge from the depths.  It has become our nightly entertainment.  And it’s way better than television.  The best show so far was on St. Barts.  Huge tarpon, amber jacks and nurse sharks kept us company every night for hours.  Where do they come from and why don’t we see them when we snorkel during the day?  Jimmy’s love of fish and ocean creatures is infectious.  And each night that I sit and listen to him yell out species that we need to come and see up close, I try to grab the words and hold them in my memory bank.  It’s sort of like listening to your third grader get excited on Christmas morning that Santa made a visit.  Adolescence will soon steal some of that wonder.  But right now, I get to enjoy it every night.  I hope every parent gets similar opportunities.  You certainly don’t need to be on a sailboat to find these moments.

This Picture Was Not Staged


Next up, our overnight sail from Anguilla to St. John, a.k.a., Sarah sees an “old colonial woman” out there in the waves . . . .

*I’m not begrudging anyone for taking vacations like these.  If you enjoy them, more power to you!  My point is that doing something outside of your comfort zone is also a really good thing to do once and awhile.  

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