Reflecting on the cost of getting everything you ever wanted

Welcome Entrepreneurs. I’m so glad you’re here.

Hard to believe, but it’s been just about a year since I left VNN, the company I founded and scaled over a 10 year period. As one does with anniversaries like this, I took the opportunity to reflect. A couple things came up in doing so.

First, after a solid year of weekly publishing on this newsletter, I’ve decided it’s time to move to a biweekly publishing cadence. I will continue to write daily because I love it, but as full as my life is getting with things I love (family, clients, really-really-cool-I-can’t-wait-to-talk-about-them projects), one thing that I realized is getting squeezed out is space. Space to enjoy the sunshine, to walk in the woods, to play golf, to read. The culturally indoctrinated part of me feels more valuable when I am productive, but I’ve finally grokked over the past year that I don’t really want what that part of me thinks it wants.

And the second thing that came up for me was this week’s post, called Blinders. With a year of space between me and VNN, now feels like the right time to reflect on that period in my life. This is one of those posts that’s a bit uncomfortable to publish, but it’s true for me, and I’ve learned that that’s enough.

Hope you enjoy.


I looked around at my life and realized that I hadn't made a choice of my own in 10 years. That moment changed everything. 

I looked around at my life and saw success. I had a big house, a BMW, a supportive family. I had a fast growing business that had launched a successful career. We went on vacations. I had all the things you're supposed to have. 

But then I read a Brene Brown article and found myself sobbing so hard I had to go outside so as not to freak out my kids. 

It wasn't that I hadn't made decisions. I had founded a venture-backed startup and had grown it to 100 employees and market-leadership. At that scale of company, most of what I did was make decisions all day: where to allocate funds, who to hire, which strategy to pursue. I did that all the time.

But when I thought about it, I realized that the last choice I made, the last time I had looked at options and really thought about what I wanted for myself and my life, was signing up for the TechStars seed accelerator back in 2010. That had been a choice. 

I could have done so many things at that point. Laura and I were talking about moving to North Carolina or Georgia for grad school, I was slowly growing my first company, West Michigan Allstar, and stringing as a sportswriter for a few newspapers. I was thinking of writing a novel. But the TechStars opportunity, the opportunity to jump in full time for three months and build the idea I'd had for a hyper-localized high school sports media network seemed too good to pass up. You only live once, I remember thinking as I made the choice to forego everything else and jump in with both feet. This is how you live the biggest life possible.

But in choosing that, I realized in hindsight, I started a process at the end of which I'd have gone to sleep for a decade. (I’ve realized since that I’m not as unique as you might think.) 

Part of the package when joining TechStars, along with the $20k in investment capital, was the expectation that you'd spend the next 12 weeks working obscene hours to build your company so that you could present it to a room crowded with investors. Demo day, they call it. The capstone of my business-school-in-a-box. The moment I chose to join TechStars, the path to demo day was laid out in front of me. So I put on my blinders, channeled myself wholly into my goal, and ran as fast as I could. 

Still, we didn't close any follow on financing on demo day, despite our high expectations. Nobody did, as in 2010 there was approximately one tech investor in Grand Rapids, Michigan, and he had already invested $20k through Techstars. I remember the conversation with my mentor:

"What do I do now?" I asked.

"Well, what feedback did you get from investors?" he said.

"We are too early for them. They don't believe we can sign up schools quickly enough."

"Sounds like you should focus on signing up some schools."  

So I did. 

That was an offramp, I realize in hindsight. A chance to look around and choose a different direction for my life. Only at the time I wasn't looking for one. At the time, I was intent on leaving my own dent in the Universe. 

By 2012, I'd signed up 30 schools and was generating about $100k/yr in revenue. After Laura and I returned from our honeymoon in Italy, I promised a few local angel groups that I could turn 30 schools into hundreds, and they asked me about my exit strategy. I had no idea, but I said we'd sell to a national media company, which seemed a reasonable enough answer. And then I had $500k in the bank, along with the expectation that I'd go sign up a shitload of schools. 

$500k is freedom money, if you want it to be. But I knew that part of the game was that I'd need to spend it down close to zero, and close additional capital before running out. TechStars had taught me that. In 2014, 300 schools later with our bank balance in the five digits and dwindling, we closed our series A round, $3mm lead by a VC from down south. 

Three million dollars. I'd never seen so much money. I wanted to celebrate, to take a second and soak in the position in which I'd found myself. Maybe I did, but I don't remember. I do remember the bone-deep knowledge I had as to why they'd given it to me. They expected me to sign up all the schools in the country. So I kept running. 

I started waking up early. 4am most days to get a full day’s work in before heading to the office. I hired and fired. Switched strategies. Scaled regionally, then nationally. Ruined our company culture because I didn't know any better, which almost ended the ride. I fought desperately to stay alive, and over time we rebuilt our culture into something new and better. That was when I learned what leadership is

I raised more money when we were running out -- sometimes with good terms, sometimes with bad, $21mm in total -- trying not to think of the little pieces of myself I was giving up each time. Of my company, I mean. 

But it worked. I hit milestone after milestone. Missed plenty, too, but accomplished the big ones. In 2018, right after crossing one of those finish lines, I remember thinking that it didn't hit as hard as it used to. I’d just gotten five million new dollars in the bank, and I remember thinking that it didn't feel like I thought it would. It felt like trading one set of obligations for another. 

I think I noticed an off-ramp even then. I saw my growing family playing in the grass just off the highway, but before I could think about what life could look like with different priorities, I’d passed it. I was going too fast. I had too many employees. My cap table was 35 people. Too many people were feeding their families on my ability to keep my promises for me to think too hard about whether those promises were the ones I wanted to make. 

By 2020, we'd signed up close to 20% of all high schools in the US. We had a plan to buy a few other companies, which would give us 50%+ market share, and just needed a bit more capital. The board came to me and said they thought we needed a CEO with experience rolling up an industry. They told me they were interested in funding the company to do a roll up, but that doing so came with the expectation that I'd hire my replacement.

I knew this was also a part of the game, that lots of founders were replaced by a professional CEO at some point. I never thought it would happen to me. I’d been eyeing off-ramps for years, but it’s different when it’s not your choice. It hurt. But I still had a job to do, so I pushed that aside and scaled up my recruiting and fundraising efforts. A few months later we'd hired the perfect candidate to roll up the industry. 

Job done, I stepped aside and realized I had no idea who I was. In a flash, the new CEO had taken on all my responsibilities, I found myself without a goal to drive toward for the first time in ten years. It felt deeply wrong.

Nothing else to do, I took off my blinders, took a breath, and looked around. With no boxes to check, I read Brene Brown and cried outside my house. With no meetings on my calendar, I ran my fingers through a stream in the woods near my house. I listened to Pink Floyd for the first time since college, just to hear that line:

And then one day you'll find /

ten years have got behind you /

no one told you when to run /

you've missed the starting gun.

I looked behind me ten years, at the last time I'd consciously chosen where I wanted to take my life. It was like meeting a high school flame again, both of you now with mortgages and remembering the time you said you'd love each other forever. 

But I wasn't that person anymore. In the space between, I'd gotten married, had two kids. Become an executive, whatever that meant. I hoped I'd helped people along the way, but I'd been running too fast to tell for sure.


In building a company from scratch, if you're successful, one thing you get really good at is setting and hitting goals. In a simplified sense, these two muscles are the building blocks of all successful companies. All the team building, culture crafting, competitive jostling, in a certain sense all the aspects of building a VC-backed company can be boiled down to your ability to call your shot and hit it. 

The most powerful tool I've found to do that is blinders. As in, focus. As in, don't let yourself think about anything or anyone else too much, so you can maximize the chances of hitting your goal. Like transforming a gentle mist into a firehose, that type of focus can break down walls.

Ten years now behind me, I realize that each goal I reached, each wall I broke, was a mile marker on the way to somewhere. Part of raising capital and scaling a VC-backed company is signing up for a very specific somewhere. An end of the road that looks like an exit, one way or the other. I knew what I signed up for in 2010.  What I didn't account for was just how different things would look after two, five, ten years. How differently I'd feel about the somewhere I'd been headed, after having arrived so many times. And how much life had happened along the way, somewhere outside my blinders. 

My twenty-five-year-old self would be blown away at what I accomplished. What I did by calling my shot, putting my blinders on, and hitting it. I’ve been all over the world, in the most influential boardrooms, and on the brightest stages.  I’ve won more often than I would have thought possible. But with blinders off, my thirty-five-year-old self looks back on the last ten years -- at my wedding day, the birth of my two sons, at so many friends entering and leaving my life, at all the things I didn’t do because it just wasn’t the right time --  and wonders how much winning is worth.  

Would I make the same decisions again? I think so. Probably. I had to go there to get here. 

But would I do it the same way today? No. In opposition to a lot of muscle memory, today I work hard to keep my blinders off. My goals call me with an intensity equal to any I’ve felt before, but today I’ve also learned to hear the subtler call of a sunrise. 

(HT: Julie Mosow, Giselle Sproule, Joel Christiansen, and Compound for editing!)

Liked this article? I’d be honored if you’d share with others who might find it valuable. 


Who is Ryan Vaughn? 

I’m an executive coach for startup founders, a role in which I get to help high-performing founders expand into extraordinary leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator, reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here.  If that’s not enough, here’s a more detailed bio.


One: How to Frame Ambition, and Not Let it Frame You (McKinsey)

If I could suggest one article to read this week for ambitious founders, it’s this one. My ambition has gotten me so much, but increasingly I’m aware of its downside. I’ve wrestled with this topic a couple times, most notably here, but author Nicolai Tillisch really nails it with this article, a transcript from his interview.


Two: Proof of New Physics from the Muons Magnetic Movement (The Conversation)

If I could suggest another, it would be any article you find by googling “muons” this week (equally interesting IMO, but may only be relevant to physics nerds like me). The physics community is up in arms around how the wobble of muons seems to contradict all known laws of particle physics. Depending on who you believe this could mean we need to entirely revamp our understanding of the laws of physics, or we goofed before. So excited to see where this ends up.

Three: Which mask are you wearing? (Waking Up)

Sam Harris’s Waking Up community raised the issue of identity this week in a 7min podcast, and I really liked it. The link is only email, so I’ve copied the highlights here:

We all know people who behave very differently depending on who they’re around. Someone who’s polite, deferential, and accommodating with their grandmother can morph into a jerk when speaking with a customer service agent. 

Now, it’s easy to judge these people as being two-faced or disingenuous. But it’s instructive to notice that we’re all in this situation to varying degrees. 

For instance, who we are on a Zoom call with a client likely feels different than who we are when speaking with a family member or friend. 

The core of who we take ourselves to be seems to remain intact, yet the face we wear seems to change, whether subtly or dramatically. It’s as if we have a collection of masks that we reflexively put on, depending on who’s in front of us. 

As you go about your day today, notice how your sense of self changes depending on who you interact with. Notice the mask you’re wearing in each interaction. 

And realize that it’s not who you really are.

Four: To Lead Better Under Stress, Understand Your Three Selves (HBR)

Last week I analyzed the way our brain’s fight/flight/freeze function, so highly adapted eons ago, now gets in our way, using hammer corals and the triune brain model. HBR tackled the same issue through an archetypal, Jungian lens, by characterizing the three selves that we each create as the Child, the Defender, and the Adult. The language is different, but I’m struck by the similarities of the insights. We might be onto something.


Five: You Were Made for This (Clarissa Pinkola Estes)

A poem for a founder:

Ours is not the task of fixing the entire world all at once, but of stretching out to mend the part of the world that is within our reach. Any small, calm thing that one soul can do to help another soul, to assist some portion of this poor suffering world, will help immensely. It is not given to us to know which acts or by whom, will cause the critical mass to tip toward an enduring good. What is needed for dramatic change is an accumulation of acts, adding, adding to, adding more, continuing. We know that it does not take everyone on Earth to bring justice and peace, but only a small, determined group who will not give up during the first, second, or hundredth gale.

One of the most calming and powerful actions you can do to intervene in a stormy world is to stand up and show your soul. Soul on deck shines like gold in dark times. The light of the soul throws sparks, can send up flares, builds signal fires, causes proper matters to catch fire. To display the lantern of soul in shadowy times like these -- to be fierce and to show mercy toward others; both are acts of immense bravery and greatest necessity. Struggling souls catch light from other souls who are fully lit and willing to show it. If you would help to calm the tumult, this is one of the strongest things you can do.

There will always be times when you feel discouraged. I too have felt despair many times in my life, but I do not keep a chair for it. I will not entertain it. It is not allowed to eat from my plate.

In that spirit, I hope you will write this on your wall: When a great ship is in harbor and moored, it is safe, there can be no doubt. But that is not what great ships are built for.

It’s quite remarkable what can happen in a year. How much life can be packed in, when you slow down and allow for some space. I can’t help but wonder if maybe that much life is always packed in, only now I’m paying attention.

Either way, thank you, deeply, for giving me this space every week for the past year. I’ll talk to you again in two weeks.

Until then, be well.


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