I had just turned 25. My birthday has been a fairly monumental day for me in my early 20s.
The day I turned 22, I found out I had gotten into Stanford Business School. I had applied on the condition that I work for two years before attending -- for what, I had no idea. I wanted to start a company.
Later that day, I had dinner with a few classmates, and we started said company. Strange how that works sometimes.
A long-standing interest in consumer products, along with a series of conversations with a good friend from school culminated that night in what would come to be my first full-time experience as an entrepreneur.
I rationalized having a business dinner on my birthday by telling myself I'd hang out with my sister afterward. My previous startup and I share the same birthday.
Two years later, also on my birthday, I wrapped up my involvement there. It had been a roller coaster ride, and I was burned out.
Oddly enough, I celebrated turning 24 at the same restaurant we'd started the company two years before -- Bertucci's, near Kendall Square, for those who are curious.
I interviewed at a bunch of places (Apple, Formlabs, a buddy's robotics startup), not knowing what to do next, but nothing panned out that made sense. I went to two of my favorite professors at MIT, both of whom know the startup game well.
Context: While the last startup was taking off, I'd asked for and received a third year of deferral from Stanford.
Issue: I still had a year and a half to go. What did my professors think?
Simple: Give back the extra year and go to Stanford the coming fall. Do not pass go. Do not collect $200.
But, deep down, something didn't feel right.
Yes, I'd cofounded a real company, and it had been an incredible learning experience, but I've learned that sometimes, you have to listen to your own intuition, especially when you're getting advice from intelligent sources.
Only you can truly know what you need.
On the personal side, I felt like I had failed as an entrepreneur, and I didn't want to show up to Stanford all ragged and torn. Practically, I know I learn more when I've done more.
I didn't want to go back to school with only one experience; I needed more.
Lucky for me, I had that third year in my pocket. I didn't have to go to school right away. I'd sold enough shares from the startup for the coming year, or so I thought.
This gap would be my gift, my curse and my learning.
Business school could wait.
I'd been dating a girl long-distance since graduating from college, and she had moved to Texas. In spite of the issues we were having, it was a chance to finally be close to her, and I needed to leave Boston — too many ghosts.
I moved to Austin in March, but my memories had yet to be dealt with. Removing yourself from the situation is one thing. Removing the situation from yourself is quite another.
In the words of my undergrad Intro To Acting professor, Alan Brody (MIT has an incredible arts program), I wasn't centered.
That spring, after leaving the startup, I began plans for a music and design studio that would serve as a lab of sorts.
There, my friends and I would test ideas and learn about a market that still fascinates me: audio and consumer electronics.
What better way, I thought, to learn about the technological problems facing musicians than to build a music studio?
We would then be able to prototype solutions right there.
Sound good? I know, it sounded good to me, too. But, things that sound good, I learned, needed to ultimately make sense on a spreadsheet, as well. Come with me to May -- the beginning of the summer, the studio and the end…
A Pick-and-Roll Summer
After having set a category record on Kickstarter at the previous startup, I fully expected to be able to list our new project at the studio: laser-engraved, anodized aluminum business cards.
Admittedly, this project was a reboot of an old side project from college, but I thought we had done a great job with the new designs.
But, just when you get a little ego, life (or, in this case, the nice staff at Kickstarter) keeps you in check.
Our metal business card pitch wasn't right for a number of reasons, and they did precisely what they should have: rejected us. We appealed, and they rejected us again -- just in case we'd forgotten.
Enter independent crowdfunding. In June, we decided to give it a whirl.
A friend of mine who works in big data visited the studio for a weekend and agreed to help the cause. Rabble rousing with him earned us some welcome press.
Though we didn't exactly earn enough to keep the lights on, we did end up learning a lot about guerrilla marketing.
Was Starting This Studio A Mistake?
Well, there were actually three mistakes: 1) It wasn't scalable (i.e. zero ability to attract investors), which meant 2) I was putting in my own money (I'd left the startup with one year of financial runway, which runs out faster when you hire people), and 3) I had a limited time horizon.
I wasn't entirely sure about business school, but the option remained.
Our challenges were best summed up by Bob, an MIT alum currently teaching at UT.
Bob Metcalfe, the co-inventor of Ethernet, namesake of Metcalfe's law and a successful venture capitalist, visited our studio for lunch as the summer drew to a close. He was genuinely nice and brutally honest, a combination I've come to appreciate.
I wasn't looking for him to invest, but I did seek his perspective on our concept.
After I explained our fundamental business model (by this point, on version four), he told us he didn't invest in lifestyle businesses. (A photography studio is a good example; Tesla, Uber and Airbnb are the opposite: high-tech, high-growth businesses.)
Then, he looked around and quietly said:
This … is a lifestyle business.
Not that I needed Bob Metcalfe to tell us we were screwed.
You Have To Laugh
I had been watching our bank account deplete all summer. Our main problem was not understanding how to make more money than we needed. I discovered that in business, this is more commonly known as a cash flow problem.
Regardless of circumstance, I couldn't help but see the hilarious irony of a tech titan kindly reading the writing on the wall.
Sometimes, you have to step outside yourself and laugh at the relative craziness of the situation in order to keep the ship afloat. If you can still laugh at that hardest point, you just might live to laugh for another week or two.
What happened next is not a story about professional triumph. There is no hero or anti-hero; stay with me.
We Need Fuel
The summer was over, and I fast came to the frightening realization we were going to have to find alternate sources of funding, ASAP. Shares of my previous startup, perhaps?
Finding a private investor was not going to be easy. My shortlist was tapped out; I would need to find someone new.
Not everyone I ran this share sale idea past was optimistic. When I asked one of the founders of Zeo (who was super generous with his time, as are many people who have spent time in the startup wilderness) about selling shares, he told me it would be impossible with such an early stage company.
My previous startup had gone through a successful seed round, but it had a long way to go. Impossible, though? Impossible can be a highly subjective concept.
An Unexpected Call
In September, I got one last email invitation to my fraternity's reunion at MIT.
I had been ignoring these, but perhaps I could meet some older alumni with more spare change than I had. Who knows?
Whenever I'm in a place of scarcity, I go to places where people, ideas and resources exist in high concentration and with a high probability of collision. I'm a huge believer in ecosystems.
I frequently hear my good friend, Ted Gonder, say, "Make mistakes of ambition and not of sloth."
Those words were written by the ever-controversial Niccolò Machiavelli.
The reunion was only two and a half weeks out, but checking flights couldn't hurt, right?
I looked online and discovered the cheapest tickets I have ever gotten to Boston. I bought them. When life throws me a bone, I do my best to catch it.
Fairly broke, I paid for only one of two dinner events the fraternity was hosting, saying I was a student for the other.
Aren't we all students at heart? I got a message from our alumni chair, who called me first thing in the morning. Oh no, here it comes -- should have paid the $60.
We chat and he tells me their alumni speaker has cancelled last minute. He'd seen my posts on Facebook (I like inspirational quotes), as well as the press from our independent crowdfunding campaign (P. T. Barnum did say once there's no such thing as bad publicity…).
Would I fill in? I would be the youngest alumni speaker in my fraternity's 120-plus-year history.
I leapt at the chance. This would be a way to connect with the entire audience, and maybe, just maybe, find someone to buy the shares.
Finding That Place
I anxiously stood up in front of the crowd, fidgeted with a mic that wouldn't cooperate with my nerves for what seemed like an eternity (about 45 seconds according to the video), but I ultimately found my rhythm.
My goal that day was to find a place of vulnerability with my audience.
It is the place where you feel as if it's only you and one of the audience members, face to face. And, though it wasn't perfect, I found that place with my audience by sharing something real.
While joining the fraternity, the term "brother" had been used a lot: The brothers feel a certain way. Why do you want to be a brother? Stay together with your brothers.
I shared with the audience that, growing up, I had lost my older and only brother, Brian, to a terminal illness. I shared that, though they may not have known it, the term "brother" meant a lot to me.
My voice cracked and my eyes momentarily took on a pronounced sheen.
I had gone there; I had found that place with them. From a room of 300, I witnessed the only true standing ovation I have ever received. More than the applause, though, it was that moment.
Living that moment was an incredible feeling, and it is one that I hope to find again.
Later that evening, I hung out with some of the more recent alums; most were familiar faces, but some were new.
Among the few I hadn't met before was an independent angel investor (read: investor in early-stage startups) who explained he had bought founder's shares before.
Excuse me? You've done what?
I can't make this stuff up. Sure, it's not that outlandish for him to be an angel investor, but for him to tell me he had bought founder's shares before was like looking down at four aces. I know it happens, but it doesn't happen very often.
Regardless, he was straightforward, friendly and had even invested specifically in the fashion space before. This guy was solid.
The following Monday morning, I pitched him with the cofounder of my previous startup.
This was admittedly awkward, but my previous cofounder and I are better friends after splitting up.
Clarity breeds confidence. Pitching with him again, we instantly entered our old tag-team. I had forgotten how fun this was.
The investor seemed excited, and if he agreed to buy a chunk of shares, he would fund the rest of our year at the studio in Austin.
Send Me The Wiring Info
Those were the magic words. It was October by this point, and after a few calls, my investor had emailed to confirm the deal.
Those are the magic words because they precede the imminent arrival of precious resources in the form of a number and lots of zeros next to it on my screen.
He was in.
By Halloween, we would have oxygen -- sweet, sweet oxygen. My friends and I would get to keep the lights on at the studio. We would get to keep exploring.
But, in the few days before closing, something new arose. My previous company was looking at a new round of funding.
Ordinarily, this would be cause for celebration. Usually, people wanting to give your company money (even when it's your former company) is a good thing.
With all the twists and turns of the past year, my world had departed from usual a while back.
Enter the right of first refusal.
I could go into the details, but suffice it to say, the company could delay the selling of my shares for up to 45 days for any reason.
In this case, the choice for them was clear: I wasn't going to be getting any oxygen, at least not for another month and a half.
When something happens, the way you respond can make it better or worse
My mom had posted these words next to the bathroom mirror while we were growing up.
I stared at that poster for what must have added up to dozens of hours while brushing my teeth. (The print-out was there for over a decade; she would replace it whenever it faded.)
Then, it sank in: When something happens, it's our response that defines the situation, not the other way around.
That delay was my reality check. The studio was out of cash and this extra 45 days would burn up the rest of our runway, effectively putting us under.
I was reminded of the winter before, negotiating my way out of my previous startup.
How could this keep happening?
I stayed in bed for two days until my then-current cofounder, roommate and best friend, Mark, leveled with me.
You essentially have two choices: Stop, or keep going. Mark knew that me lying there in bed wasn't going to solve anything.
True Friends Will Give It To You Straight
It was time to face the music, and somehow, that not only made everything more tolerable, it pushed both the situation and me forward. Clarity breeds confidence.
We were not a business, and now, our studio was in total jeopardy.
The fraternity investor wasn't happy; I wouldn't have been, either. Delayed?! I don't care how much or how little skin in the game you have. Who likes waiting?
Life, It Seems, Is Not Without A Sense of Irony
Life had a lesson for me. We were broke, and I had to lay off Mark. It was the ultimate déjà vu; I was voted out of my previous startup one year before.
People sometimes ask why I left. It wasn't any one thing with the startup; it simply wasn't working.
When you ask investors in startups what the biggest risk is, they will often say, "Teams." It is hard for people to work on something together with such promise, acceleration and risk.
Etched into my memory is the incredible pain I felt the night I spoke with my cofounder about the fact that it wasn't working. It's not something you want to relive or repeat, but here I was again, only this time on the other side.
Though the situations were very different between the startup and the studio, I couldn't help but notice the similarities.
Life can be a funny teacher. Now, it was my turn to learn what firing someone you care about was like from the other end.
Mark had anticipated the imminent demise of our project's current incarnation as we had actively discussed the studio's financial woes, but that didn't make it any easier.
Honestly, it was nothing short of extremely frightening, but I attempted to communicate with the greatest amount of respect and kindness possible.
Oscar Wilde once said,
True friends stab you in the front.
I apologized for the share delay and promised to help in any way I could, but nothing could change the fact that this sucked.
Regardless of circumstances, I find it hard to think of a situation where firing a friend and colleague for any reason feels anything remotely close to good.
Ultimately, we made it through, and we're best friends to this day. That is as much of a testament to his attitude as it is to anything I said or did, and I aspire to that level of maturity.
Sir Winston Churchill said,
If you're going through hell, keep going.
The 45 days of share purgatory taught me what it means to be an entrepreneur; to deny death and, instead, to courageously approach life.
Mark and I both began ferociously freelancing from the studio.
He ended up landing a little bit of web design consulting, and I ended up jamming as an essay editor for grad school applications. All hail the virtual economy.
Uncertainty is a strange thing. While it can often paralyze, it can also serve as a catalyst to push you to spring into action.
And so, it was with us. Though I didn't feel like getting a 9-to-5 job, I also explored that avenue by securing a job offer for the months leading up to business school.
Still, hope springs eternal. At the end of the 45 days, the investor had a few more questions. Understandable. No big deal.
But, inside, I was on pins and needles. By that point, I was exhausted -- waiting can do that to you if you're not careful.
Use The Moment
Back to that cold winter night in Austin.
I was now 25 years old, and the immense uncertainty of the share delay hung over me. Our fate had yet to be decided, and I seriously contemplated retreat. I thought about closing myself off again, frustrated and angry at a world I could not control.
But, something within me stirred. In limbo, I saw with remarkable clarity that the path forward was a simple choice. In the face of fear, I remembered Mark's words: Stop, or keep going.
That night, I began training for the April marathon I'd signed up for the previous summer. Because why not?
Running along that path, I experienced an overwhelming surge of emotion. I am a privately religious person, and I generally prefer to keep it that way.
But, alone on that trail, I began to speak aloud:
What do you want me to do? I'm here. I'm ready. If you want me to get a job before school, fine. I'm fine with that. If you want him to buy the shares, fine. If it's something else, fine. I'm ready. It's not about me.
The real gift here is not what happened afterward, but rather, the moment itself. It was a moment of utter humility, one we must all eventually face in the arena.
It's the realization that the universe is bigger than we are, and that's okay. It's the understanding that there is a certain amount of blind, yet active confidence required to play this game, and we must have an equal, if not greater, amount of straight-up willingness to respect the game.
To respect the process of exploring the unknown is to make something new. I heard Bollywood Star, Shah Rukh Khan, say it perfectly when I saw him speak about resilience: "There will be losses."
What that means, however, is not rolling over and playing dead. Screw that. Capitulating to inaction and complacency produces little and accomplishes less.
Instead, in the face of uncertainty, run — somewhere, anywhere. Find balance in the noise.
Be productive; move, and if you're tired, rest, but don't forget to wake up. It's much easier to turn in the right direction once you're moving. Stop or keep going.
In my year in the wilderness, I found what had so often eluded me before: balance. Balance in great friends and in fighting the urge to control things beyond my control. Balance that frees me up to tackle what I can control.
Balance that lets me stand in a raging storm while I close my eyes, if only for a moment, and feel solid ground beneath my feet.
Fear is a Teacher
John Harthorne, the cofounder of MassChallenge and a wonderful mentor, told me that in my gap year, I would encounter a moment of fear.
I should allow myself to become immersed in that fear because it had things to teach me I couldn't learn anywhere else.
He also said to never completely believe it — to never grant it that power — but to still allow it to engulf me, to teach me.
On my run that night, I experienced that moment of real fear.
And, it taught me that if nothing else, there are at least two things we can control: our desire and our actions.
It's the belief and willingness to carry out our dreams. Much is up to the world, but the rest is up to us.
Two days later, I was at a belated birthday dinner, and I got a text message from my investor with a straightforward question about the investment terms, which I then knew by heart. I responded immediately, and the investor did, as well.
The money will be wired in the morning. I took a deep breath and smiled. Oxygen. Didn't I tell you birthdays are awesome?
This part of the story reminds me of one of my favorite quotes from Malcolm Gladwell's "David and Goliath," as he discusses the survivors of the Blitz on London in WWII. Gladwell cites Dr. J. T. Maccurdy, who says the conquering of fear produces exhilaration.
The contrast between the previous apprehension and the presence of relief and feeling of security promotes a self-confidence that is the very father and mother of courage.
We'd made it through the crucible, and I could feel a new dawn rising.
The Real Success
The real success that winter was not, however, the share sale.
There was something deeper going on -- something different, something new. The real magic was not in the circumstances or the outcome. The real magic was in my new, changed response.
One of my favorite movies, "The Shawshank Redemption," put it best:
Get busy livin' or get busy dyin'. "Stop or keep going.
In a world of comparison where we go online to see a catalog of our friends' favorite memories, I found I had to look inside myself and ask, "Do I want to do this? Is this worth it? And, if so, how can we make it happen?"
And, then, I had to search the world for the answers. Because they do exist; you just have to look closely.
The nine months that followed encompassed one of the most creative times of my life.
We got to use our studio to learn and build, hosting over a dozen design weekends with friends, the most notable of which brought my previous cofounder and I back together in a meaningful way (designing and building a table together will do that for you).
He and I took the time with a few close friends to have discussions that enabled us to take our friendship beyond its then-awkward state into a brighter reality.
Clarity breeds confidence.
Personally, I grew, both finishing the Big Sur Marathon and earning my pilot's license, which had been put on hold the previous summer.
Flying is special for me. We lived by the Austin airport, and every time I heard a plane overhead, I vowed I would make it back to the sky.
More than any singular accomplishment, I found my center again, reaffirming why I want to continue building companies.
I decided I would go back to school and attend Stanford. I started last fall.
Time in the wilderness can teach us so much. In the wilderness, we experience fear in a very real way.
The wilderness shows us fear is not to be avoided. Instead, fear can be a bright light, showing us in stark contrast what we must change. And, that change often starts within.
What you know today may not get you to next week, but if you can make it to tomorrow, you might find what you need.
This isn't a secret; it's the kind of flexibility I have observed in people with extreme levels of grit, and it is an attitude I strive to emulate.
We live our lives so often avoiding pain. No one wants to get hurt; the idea of getting hurt scares me, too. But, what truly frightens me is the notion of never having fully lived in the first place.
The studio was a magical place, but deep down, I always knew I could not stay there forever. I remembered Robert Frost's beautiful words:
The woods are lovely, dark, and deep. But I have promises to keep. And miles to go before I sleep. And miles to go before I sleep.
Our time in Austin has come and gone, and I now know what the wilderness was trying to teach us: Some of the best experiences are born from some of the hardest. Fear into fuel.
True alchemy, it seems, does not lie in turning metal into gold, but rather, in turning painful experiences into joy and learning. I looked up the word, alchemy, just now. And, I think the definition I found describes our time in the wilderness perfectly:
Al·che·my: a seemingly magical process of transformation, creation, or combination.
Author's Note: This article was in part inspired by Ted Gonder's Managing Your Own Psychology as well as Andy Dunn's The Risk Not Taken. This article, like the past year has been the product of great friends. I deeply appreciate help editing and feedback from M.S. Rustagi, Cindy Sui, Luis Navia, Ted Gonder, Franklin Russell, Ross Pedersen, M.F.E. II, & Camilo Ruiz. And to you, the reader, I sincerely hope you found this story useful.