The Prologue | Moving Fast with Domm Holland

Overnight success takes a decade. Though coverage of today's founders often makes staggering success and hefty raises look commonplace, behind each story are many others. Tales of unpleasant old jobs, failed businesses, dead ends and disappointments. The Prologue is a series by The Generalist about what came before an entrepreneur's big break.

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It was a small moment amidst big news.

Fast, a startup building a 1-click checkout for the web had just raised its $20MM Series A. Domm Holland, CEO, took to Twitter, a platform on which he’s active most days, to share the news.

“[Co-founder Allison] and I, along with the whole Fast team, have been working tirelessly to make the web faster and easier for everyone. Proud to announce that Stripe have now joined us in that mission. 🙌 1-click checkout is coming to everyone!”

Congratulations populated the comments section. It was, after all, an impressively sized round and in Stripe, Fast had secured the support from arguably the most prominent private fintech company in the world. But among the well-wishers, there was one exchange that caught the eye. In response to the news, one user shared his thoughts on Stripe’s involvement succinctly, “Future acquisition.”

From the outside that might make sense. Stripe recently raised $600MM at a $36B valuation and is widely considered to be one of the best-run companies in Silicon Valley.

Without missing a beat, Domm responded. “No, we have no ambition to buy Stripe, they are a great partner 😄.”

In my conversation with Domm, that interaction stuck in my mind. In part, because I think it summarizes him: unbridled ambition with a grin. Over Zoom, Domm was game to talk about anything, but there was no mistaking that behind that friendliness is determination and big plans.

In this edition of The Prologue, you’ll have a chance to hear about Domm’s childhood dreams, the company he started to impress a high-school girlfriend, and what boxing taught him about business.

Brief

  1. Learning to fight like Kostya Tszyu

  2. Following in Michael Dell’s footsteps

  3. Scaling a business to $10MM in 12 months

  4. Serving governments and managing stress

  5. Using Whatsapp like a weapon

  6. Answering Harry Stebbings

  7. How Product Hunt and a16z showed he was onto something with Fast

  8. Tubthumping with Elon Musk, Jeff Bezos, and Frank Sinatra

Origins

What he wanted to be growing up

As a kid, I always wanted to be an army commando or Navy SEAL. Those just felt like the coolest, most intense jobs you could have. To be honest, I kind of still wish I could do them. Now at least, I get to live vicariously through my trainer, who used to be a commando.

Early heroes

I didn’t have entrepreneurial heroes growing up. I was interested in Bill Gates, but I didn’t study him obsessively. I’m a little older than many other founders in San Francisco, and in some respects, I grew up in the pre-internet era. I probably didn’t spend as much time learning about those entrepreneurs. Today, I have massive respect for Jeff Bezos. What he’s built is amazing.

My real role-model was a boxer: Kostya Tszyu. He’s a Russian fighter who immigrated to Australia. The first-ever boxing match I watched was Kostya Tszyu versus Zab Judah. Tszyu got the knockout. It was incredible to watch.

Picking fights

I used to pick a lot of fights when I was younger. I got the crap kicked out of me because I was small with a very big mouth. And so I remember watching that fight with my ex-stepdad one Sunday, sitting in the pub. The next day he took me down to the youth center to start taking boxing lessons so I could learn to protect myself.

In hindsight, that was a pivotal moment in my life it changed a lot for me. Boxing became an outlet: I lost weight, became more confident, and felt happier.

Beginning to code

I have my ex-stepdad to thank again. He’s a computer scientist and was a lecturer at Stanford as well as some Australian universities. He’s a tough man. One year, when I was fourteen, he set a book in front of me called The C Programming Language written by Brian Kernighan and Dennis Ritchie. And he just said, “Read this book and do all the exercises.”

The Palindrome Machine

I’d never programmed before, but it turned out that this was a book designed for third-year computer science students. Once I completed the book, my ex-stepdad gave me a project: create a script that could tell whether a word was a palindrome. That was the first piece of software I built, this quirky little product.

In the arena

Company 1: Buy Technology

When I was fifteen, I started an e-commerce company that sold used computers. I’d find components, build the computers myself, then sell them online. I had a girlfriend at the time, and I wanted the money.

I remember getting called into the principal’s office at my boarding school. The headmaster told me, “Dominic, you’re not in trouble, but we’ve received a fax ordering $5K worth of computer equipment.”

And I said, “Fantastic! I’ve been waiting for that.”

He thought it was great that I was being entrepreneurial. But he did ask me to stop using the office staff as a makeshift admin team for my startup. Fair enough.

Inspiration from Dell

Because that’s where I got my start, I’ve always really enjoyed the Dell story. Michael Dell built and sold computers from his dorm room. It’s crazy that it’s not a more popular story because here’s the kicker: Dell did $80MM in his first year of operating. $80MM! Out of his dorm room with $1K in startup capital.

That’s something I still think about a lot. No matter how fast I think we’re going, I remind myself we can move faster.

Dropping out

I used to get bored pretty easily, so after a while, I wound Buy Technology down. Not long after, I went to university. I’d gotten a scholarship to attend the top computer science school in the country, but I left after just a couple weeks. I really wanted to join the workforce. I ended up starting in door-to-door sales, then debt collection, before joining Dell of all places. It was one of the best places I ever worked. After a while, though, I knew I wanted to start selling my own products again.

Company 2: DMDN

My wife’s family is in the automotive industry, so through them, I got to meet a lot of car dealers. That opened my eyes to the sector: how massive it is, and how out of date. I started building tech to help dealerships better run their operations and managed to scale pretty quickly. In 12 months, we had more than 100 employees and did +$10MM in revenue.

Limitations

Even though we grew quickly, there were fundamental elements of DMDN business that capped our potential. For one thing, we were very reliant on one customer. That’s something I learned to be more conscious of in the future, though I faced similar problems in my next business. Beyond that, DMDN was also service-based. Over time, I’ve focused much more on product companies.

Company 3: Tow

For a moment there, Tow was one of the fastest-growing companies in Australia. We were named to Deloitte’s 2016 “Fast 50” list and transacted $50MM in four years. We had a fantastic business: providing on-demand towing. Clients included multiple government entities, as well as multinationals.

From paper to the cloud

The towing industry is one of the most traditional sectors in the world. It’s very old-school. When we started, most customers operated like it was the 1990s. They made phone calls to dispatch individual trucks manually and filled out paper forms. We digitized everything. In the process, we brought transparency to an opaque market. That was part of our undoing.

Managing stress

The whole experience taught me a lot. About working with governments, for sure, but also about the legal system and stress management. Trying to keep the business alive while we were dependent on just a few customers caused me a lot of anxiety. Today, I think emotional equilibrium is one of my strong suits. A lot of that stability came from handling the ups and downs of Tow.

In the arena

The inspiration

I have two kids I came up with the idea for Fast while my youngest was sick. He was in the hospital 24 hours a day, so my wife and I had to split our time between the hospital and home. My wife’s grandmother helped us during that period, and part of that was doing the little things, like making sure we had enough groceries in the house.

One night, I remember, my grandmother-in-law was trying to place an order online and because she forgot her password, she couldn’t buy the groceries. Despite this being a reputable site, despite her being a good customer, she quite literally couldn’t place an order.

It was so clear to me at that moment that passwords are broken. I remember thinking, “they just don’t make sense.”

Product/market fit

In two days, I built a passwordless authentication product and launched on Product Hunt. Things went crazy. In just a few days, tens of thousands of people had used Fast. Just a couple days after that, I’m sitting in regional Queensland, and Andreessen Horowitz reached out. They said, “We love what you’re doing want to jump on a call?”

My son was still in the hospital, and Fast was a five-day prototype. To get that level of interest from both users and investors? I knew immediately this was going to be a big business.

Lessons

Learning from the ring

Boxing is an incredibly gruesome activity. And not just because you get punched in the face. I fought competitively for years, and nothing drains your energy faster than someone rushing at you, trying to knock you out. Every muscle in your body is being exercised, and your mind is running a hundred miles an hour trying to predict what will happen next and make sure you don’t get knocked out.

It’s hard work. It takes discipline and motivation. That’s how boxing has helped me in business I’ve become accustomed to training hard every single day and translating that effort into the rest of my life. I have a strong work ethic.

Giving employees the tools to succeed

(H/t to Harry Stebbings for the question)

Onboarding staff is something I think about a lot, and Fast as an organization thinks about a lot. You want people to be excited from their first day and first interaction with your company.

We renovated our office space completely as soon as we moved in, so it’s a great experience from the first physical touchpoint. The first thing Fastronauts see is our green living wall. We also give our team great equipment, which means more efficiency (people produce better work faster, and it makes people happy, a win-win).

The last thing you want new employees to feel when they start is lost. We want every employee to understand what we’re working on, like how heavily we’re investing in security so that every person can communicate with every part of the company. We also try to answer everyone’s tech questions preemptively we’re moving toward zero-touch laptop deployments, so employees know which apps to download and preferred tools to use right from the beginning.

Leveraging Whatsapp

I’m lucky to have a lot of people I can go to for advice. I don’t necessarily have just a single mentor, but a brain trust that I can contact with the press of a button. One of the best tools to leverage their expertise is Whatsapp. I’m not joking when I call it one of my prized possessions.

Killing friction

My work at DMDN and Tow focused on tackling problems in analog sectors and bringing processes online. In some ways, the lesson from that is that there’s opportunity in digitizing old-school markets. While I think that’s true, I think of the through-line in my work a little differently: it’s about killing friction.

Even in spaces that are technologically-savvy, there are so many points of friction. There’s so much that can be overhauled and reimagined. When I think about Fast, that’s at the core of what we do. Killing friction and giving customers their time back.

Digressions

A book that impacted him

Honestly, The C Programming Language. That book set me on a different path.

The theme song to his life

“Tubthumping” by Chumbawamba. You know, “I get knocked down, but I get up again.” (Ed: There was zero hesitation in this answer :))

The best advice he’s ever gotten

“Expect the unexpected.”

I heard that in a movie when I was younger, and it stuck with me. At this point, that mantra is ingrained in my system. I try to be as ready as possible to jump on anything that might crop up. That’s part of my job as a CEO.

The last product he fell in love with

Figma. I love everything about it. In terms of business workflow, I think it’s one of the most transformative products that’s been built for a long time. I’m not a designer our designers at Fast would laugh at the idea of “me” and “designer” in the same sentence but I’m just blown away with the product. I think a lot of valuable businesses will be built with Figma’s principles in mind.

It also has an important role in Fast’s founding story: I designed both the original and current logos in Figma. It’s one of the reasons I was so excited and humbled to have Dylan, Figma’s CEO, invest in our last round.

His fantasy dinner guests, dead or alive

Jeff Bezos, Frank Sinatra, and Elon Musk. I’d love to see what would happen with that crew. What would Elon get up to? Can I bring Muhammed Ali, too?

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