My philosophy is simple: a life with plenty of mistakes, but no regrets.
When I was younger, I was always striving for 100 percent. I wasn’t trying to beat somebody on the test. Rather, I competed against the thing itself, not the person. That mindset carried forward — I’ve always measured myself against the standard, not against peers.
You can be competitive and push to win. Sometimes you’ll fail, sometimes you succeed. You pick yourself up and learn from it. But as long as you never get into the gray area of your own personal ethics, there are no regrets to the mistakes.
I’ve had failures along the way. They hurt, those failures leave marks. But they also form who I am now. The two years I spent as a turnaround CFO aged me like dog years. The company had six months of runway left when I walked in. Every decision was urgent. Every day I’d count how many times I muttered “Seriously?!” at some broken process. My ‘Seriously Quotient’ was usually north of one per hour — never a good sign. I knew that if we didn’t pull it off, people would lose their jobs and investors would lose all their money. Still, we managed to extend the runway, restructure, and sell it after two years. But I walked away with gray hair and a deep appreciation for how fragile everything really is.
“Every day I’d count how many times I muttered ‘Seriously?!’ at some broken process. My ‘Seriously Quotient’ was usually north of one per hour — never a good sign.”
We knew it was risky. It always is. But we believed in it enough to go all in. She became the CEO. I took the CFO role. Our third partner was the CTO. Together, we built it to forty people before being acquired.
Those five years were some of the most intense of my career. It was twenty-four seven. Building the product. Raising money. Scaling the team. Designing the office ourselves because it mattered what the space felt like. And always knowing that the choices we made determined whether the people who had trusted us with their livelihoods would still have a job in six months.
That’s the scariest part of entrepreneurship — the part people don’t talk about enough. It isn’t competition. It isn’t even failure. It’s the responsibility.
When you’re just responsible for yourself, or a handful of people, the stakes are high but containable. Once you start hiring, you carry other people’s lives on your shoulders. Payroll is coming. Rent is due. People have families. And you know if you screw it up, it isn’t just your mistake — it ripples out to everyone who trusted you. And as the team grows, the scale of the outcome needs to be so much bigger to make a meaningful difference in the lives of the broader team when the company exits.
“That’s the scariest part of entrepreneurship — the part people don’t talk about enough. It isn’t competition. It isn’t even failure. It’s the responsibility.”
There were nights I lay awake staring at the ceiling, replaying decisions in my head. Did we hire too fast? Did we stretch the product roadmap too thin? Are we missing something obvious? That weight never goes away. You learn to carry it.
We sold the company, and I stayed for six months to transition things inside the acquiring company. After that, I stepped away. Not because I didn’t love it — I did — but because I had poured everything I had into it, and it was time to let others carry it forward. There’s relief in that, but a sadness that you are no longer directing the thing you built. A startup is like a child in some ways. You love it, you nurture it, and at some point you have to let it grow beyond you.
Through all of it, I leaned on systems. I’ve always hated wasted motion. I love efficiency. I don’t like doing the same thing twice. If I can automate it the first time, I will. In consulting, that meant building spreadsheets that could be reused instead of redone from scratch. In a startup, it meant setting up processes that meant the team wasn’t reinventing the wheel every month.
And when the work felt too heavy, I leaned on what I call productive procrastination. If I didn’t want to tackle a problem head-on, I’d pivot into something adjacent — redesigning a board deck cover, automating a report, rewriting a model. It was still procrastination, but at least I had something tangible to show for it when I circled back. That approach saved me more times than I can count.
I’m a deep introvert. I love people, but by the end of a week of meetings I’m burned out. Painting became an honorable excuse for solitude: I’m in the garage painting. That was restorative. After a week of decisions with millions of dollars and dozens of jobs at stake, standing in front of a canvas where the only question was whether I liked the color was pure freedom.
Looking back, there were plenty of mistakes. Hiring too slowly at times, too fast at others. Chasing one feature too long. Underestimating how quickly the market could shift. Plenty of mistakes. But no regrets.
Failure is inevitable. Regret is optional. Draw your line early and refuse to cross it. That way you can push hard, fall hard, and still look yourself in the mirror. That’s the long game.
Mistakes are inevitable, but regrets don’t have to be. I’ve lived this philosophy as a turnaround CFO, extending a company’s life when it had only months of runway left, and as a co-founder building Accompany from an idea on a whiteboard into a forty-person team later acquired by Cisco.
The hardest part of entrepreneurship isn’t competition or even failure — it’s the responsibility of carrying other people’s livelihoods on your shoulders. That weight never goes away, but you learn to carry it.
I lean on systems, efficiency, and what I call productive procrastination to keep moving forward. And when the work gets heavy, I turn to painting — a reminder that freedom and creativity balance the responsibility.
The long game is simple: failure is inevitable, regret is optional. Draw your line early and refuse to cross it.
Last week, I had a chance to share some thoughts on my founder experience (Accompany 2013 – 2018) with Aaron McDaniel’s Haas MBA 295A entrepreneurship class.
Fundraising is a constant focus for us as entrepreneurs, and it’s a topic that comes up nearly every time we meet. The startup world is filled with stories about founders pitching to dozens of VCs, going from meeting to meeting, before finally securing that elusive first round of funding. For those of us willing to invest in our networks, I completely disagree with this approach.
Yesterday, I had a chance to share some thoughts on my founder experience with Accompany with the latest LAUNCH Cohort.