What a decade of building a venture-backed company really taught me.
In 2011, I heard a public-radio underwriting spot that changed my life. WNYC’s Radiolab ran the “Undercurrent, a digital strategy firm in lower Manhattan thinking about human–refrigerator interaction, 3D printing, and cat memes.” I cold-emailed them: need an IoT expert? Months later I was in GE’s executive dining room atop 30 Rock discussing future of GE’s overall strategy.
The epiphany that led to Parabol came not in a boardroom but in a blizzard. Working for Undercurrent I had taken a car from Brooklyn up to GE’s old Fairfield Connecticut headquarters hours through the driving snow just to meet by using their executive video conferencing room. Why did I need to travel? On the ride home I wrote down the thought that became Parabol: software will eat the office; the majority of knowledge workers will work remote at least some of the time.
At Undercurrent we’d adopted Holacracy and leaned on structured, facilitated meetings to unlock decisions. We routinely led workshops that relied on much simplified, related facilitated structures to minimize politics while maximizing progress. When Undercurrent was acquired in 2015 and the acquirer swiftly went bankrupt, I decided to start Parabol to build those facilitation mechanics into software—beginning then with a too-small market to facilitating team Check-In meetings for our friends at August Public, and later expanding to Agile meeting formats popular in product development led to our early successes.
“The days are long but the years are short” is an aphorism often applied to raising kids. Reflecting back on 10 years of Parabol, that pithy observation fits. After years of early struggle, some success, and navigating periods of intense global and societal change I feel we’ve learned a lot and our best years still ahead of us. We’re doing the best work we’ve ever done and the company feels more relevant than ever.
One of Parabol’s cofounders, Terry Acker, tags wins with the 0️⃣ emoji. He borrowed an idea from a team that declares the score “0–0” after every goal. The idea is simple: no matter the last play—win or loss—the stakes reset. That’s how I try to run Parabol now. Process the past; don’t be bound by it. Plan for the future; don’t dread it. Stand fresh on the field and play your best game today.
In the spirit of “processing the past,” below are a few of the most notable things I’ve learned starting and operating Parabol over the past decade.
What I thought success would look like (and what it actually did)
I’d previously worked at two startups and believed I could raise a seed financing round on a deck alone, work together with a small team in shared office, iterate quickly, and find product-market fit like a well-paced montage. Instead, it took nearly 5 years to raise institutional capital. 200 investor meetings all told me remote work, “would never amount to a substantial market.”
I largely self-funded the company by continuing to consult and gave the majority of my wages to my cofounders as we slowly built our initial product. Iteration was slow and expensive.
Did I think I’d still be CEO in 10 years? Yes. I am irresistibly drawn toward responsibility and risk. I love my job.
“A man is a success if he gets up in the morning and gets to bed at night, and in between he does what he wants to do.”
– Bob Dylan
The moments that bent the curve
Using GraphQL before it was cool. When Matt Krick joined and rebuilt our stack around GraphQL and built our own real-time pub/sub implementation before it was in the spec, our first live team meeting on Parabol felt like lightning in a bottle. While we’ve iterated our architecture substantially, we’re still based on the GraphQL patterns we established 9 years ago.
Bottom-up adoption from big orgs. In 2017 when a U.S.-based home-improvement retailer signed up organically and internal usage grew virally, I thought, this company might actually work!
COVID whiplash. The week the world locked down, signups jumped from hundreds to 4–5k per week. We were just 5 people. Matt and I re-architected the product to vertically scale in 72 hours (and barely slept). Investors pre-empted with our Series A; my anxiety rose faster than the line on our usage graph.
Setting limits to ring our cash register. Another large U.S. retailer had thousands of free users but a VP who communicated “there is no real demand for Parabol” We shipped a feature that temporarily locked out their teams and displayed a message with a button the retailer’s employees could press send that would email that VP and request Parabol be unlocked (along with my phone number). The VP called to chew me out but a PO followed just hours later.
Defense adoption. Seeing thousands of U.S. airmen and contractors sign up broadened our sense of where structured, semi-async collaboration mattered. I lost sleep worrying about what kind of data these folks were adding to our public SaaS. I channeled that worry to reach out to senior defense staff and soon won several contracts to provide secure, accredited instances for them to work on and scale.
The moments worth losing sleep over
Silicon Valley Bank’s collapse. I was in San Francisco meeting with several firms close to leading our Series B. Instead of putting money in our bank, we had to figure out how to get our assets out before the bank collapsed. We didn’t. For several days we worried how we were going to make payroll. Most investors froze, CRV moved quickly. It’s in moments like these people’s true stripes become clear.
The aftermath. The shock to the investment market removed all possibility for closing a Growth round at that time. Our attention changed to extending runway. Many teammates voluntarily took pay cuts—a humbling sign we’d built a place people believed in and would fight for. We were able to recapitalize. However, re-budgeting has meant many painful goodbyes.
Alongside the business headlines were human ones.
The mind is willing but the flesh is weak. In early 2021 my mother-in-law came to help us care for our two-month-old son and unknowingly brought COVID with her. She was hospitalized and thankfully soon recovered; I developed Long COVID and spent ~12 months largely bed-bound, surfacing only for critical meetings. As the principal product driver, my absence slowed our ability to invest in innovation.
Dangerous lies told as truth in startup culture
Working within the venture-capital system taught me that luck is an underweighted variable to success. Investors like to talk about pattern recognition; the patterns often ride demographic shifts, pedigrees, and macro trends beyond control. I learned your batting average matters, but you don’t get to choose when a pitch comes straight down the middle.
What is in your control is tenacity and preparation. Stay on the field long enough and you learn what you’re made of. One aphorism that is true: a CEO’s first job is to not run out of money.
Year one, everyone warned: “If a founder leaves, you’re dead.” Shortly after our first term sheet arrived, one of Parabol’s cofounders exited our business. I braced to tell CRV. The partner said, “This actually happens all the time—here’s how we handle it.” The real lesson: investors care most about market signal and evidence you’re on an exponential, not continuity nor harmony among the founders.
Leadership mistakes I had to unlearn
Before Parabol, I worked at a consultancy, Undercurrent, that transformed from a traditional partnership into a self-managing organization—the dawn of a golden period fueled by transparency, empathy, and data-driven decisions that led to rapid growth, strong talent acquisition, retention, and success with clients. I tried to port that culture one-for-one into an early-stage startup.
We hired purposeful, values-aligned people. We built a great place to work—probably faster than we built the best tool to do work. I under-weighted selecting comfort with risk as a hiring dimension. This caused us to take smaller, more cautious steps when we needed to stay bold. Over time I learned to tune the company’s risk profile and staff our business with folks who thrive amid uncertainty.
Another lesson: don’t scale on an uncertain business model. During the pandemic our usage exploded while our revenue model and sales motion were still forming. Conventional wisdom—amplified by our board—said, “Spend faster to raise faster.” If we’d fully complied, we’d have run out of runway in a year. I should’ve trusted my gut to keep the team small until the model repeated predictably.
And beware metric-hunting. It’s tempting to stare at a funnel and decide that nudging signup→activation by 5% will unlock your next round. You’ll burn quarters and barely move it. Early on, swing for changes that make the whole journey better. Even misses generate more insight than button-placement tweaks.
What’s next
Parabol is in our most inventive period since our founding. We started by guiding Agile ceremonies and semi-synchronous collaboration. Now we’re expanding from meetings to workflows—any structured process teams can imagine, run on their own time, with software doing most of the orchestration. I can’t wait to put it in users’ hands.
Ten years in, through peaks and gut-checks, the score is still 0–0—and that’s exactly how I like it.
To my enterprising parents for making entrepreneurship look cool. Thanks also to Johanna Beltowska, Mike Arauz, Clay Parker Jones, and Aaron Dignan for taking a chance on a hardware nerd and teaching me to design organizations, not just products. To Taya Miller for helping us get off the ground. To Adam Pisoni, all the folks at August Public, Jason Spinell, and Tim Mayeur for the early financial and emotional support. To NOBL (especially Bud Caddell) and all of The Ready for giving me work during our early years. To Taya Miller for helping us leave earth’s atmosphere. To Terry Acker for turning big ideas into digestible products and being the bedrock of who we are and strive to become. To Matt Krick for challenging us, building the architecture, and accelerating us forward. To Grayson Crickman, Aviva Pinchas, Taylor Hanken, and Kendra Dixon for pouring the many foundations we have built this business upon. To every teammate, advisor, investor, user, and customer—especially the ones who challenged us. You made us better.
