Insight from those who have founded multiple companies
There’s a societal reverence for the entrepreneur. Cities vie to be startup-friendly. People admire the risk-averse initiative required to start a company. Even the West itself is built on entrepreneurs who dropped everything to start a farm, timber company, or mining operation.
It takes a certain kind of person to start and run a business, but to do that many times over requires guile few possess. Those serial entrepreneurs form a group of business people who are multifaceted, easily bored, and a little crazy.
“We focus on what’s possible as opposed to all the things that could go wrong,” said Terry Drayton, who has founded eight companies, most of which were headquartered on the Eastside. “Any entrepreneur who is sane enough to be objective about where they are at any point in time would probably be in the fetal position and never get out of bed.”
Talk to people who have founded multiple companies, and you’ll uncover some common defining traits. On the following pages, you’ll meet some of the area’s serial entrepreneurs and find out what it takes to say, “One business isn’t enough.”
1. Ideas for Improvement
People can spend much of their careers chipping away at a single task, like a scientist researching a certain field or an engineer working on various iterations of a single project. Serial entrepreneurs aren’t motivated by fine tuning, though — they’re always looking to make monumental changes, regardless of industry.
“My wife calls it the sickness,” said Dave Parker. “On my hard drive at any time, and on Evernote, you would find a dozen (new company) ideas.”
Entrepreneurs who start a single company see the world through this lens, too, but their focus sharpens once they start a company or remain within an industry. Starting multiple companies across multiple industries, however, requires constant analysis of markets and a realistic sensibility about how a company might help a perceived customer desire.
“It’s seeing that the current customer experience sucks, and that there’s a way better way of doing it,” Drayton said. “I like to learn something brand new. When I sign up in an industry, that fact that I don’t know anything about it doesn’t bother me at all. You have all your experience and background … but I’m completely comfortable with uncertainty.”
To serial entrepreneurs, the world is a big Rube Goldberg contraption. If they find an aspect of the market that can be simplified, they don’t just say, “What a shame.” Instead, they learn the necessary skills, hire the necessary experts, and start a company with the intent to capitalize on a market void.
2. A Wandering Mind
Some dream of starting a company and guiding it to the multibillion-dollar realm. It’s a lofty goal, one that usually takes a lot of time — far too much time to ask of a restless serial entrepreneur.
“I like the 0-to-60 phase,” said Mary Jesse. “I really like the phase where you’re starting something from nothing and you’re struggling to make an idea happen, whether it’s a new project or company.”
As folks constantly looking for the next big thing, most serial entrepreneurs find the minutiae of honing companies boring. They like implementing big changes in a short time, and starting a company from scratch is the best way to achieve that goal.
Serial entrepreneurs’ short attention spans can in part be attributed to their definitions of success. One-off founders want to guide their companies to the highest realms of profitability, and employees want to be a part of that mission. Serial entrepreneurs want to get the ball rolling on starting a problem or creating a segment. Once that’s been accomplished, a mix of seeking the next adventure and creativity leads them to start another company.
“There are a lot of cases where people do just start a company, and it ends up doing well and they have an exit and they’re happy; they’re good,” said Sean Muller. “But true entrepreneurs don’t like to be bored, don’t like to not work on something significant. It drives them nuts.”
3. Be your own Boss
We’ve all had bad bosses. They stifle creativity, treat employees like machines, or disregard any external circumstances. Everyone hates those bosses, but serial founders find themselves disliking working for even the best bosses.
“What motivated me? I guess adventure, and the knowledge that I’d be a terrible employee,” said Andy Sack.
Serial entrepreneurs aren’t blind to the benefits of working as an employee. The money is stable, the hours are more predictable, and most of these folks are talented and versatile enough to command top salaries. But employment doesn’t offer the risk or the accountability that comes with running the show, even if that job is in the C suite.
“When you’re a president or CEO of a company, you’re implementing someone else’s business plan,” said Joe Verschueren, “but when you’re a founder, you’re creating it.”
The sink-or-swim nature of founding a company can be addictive. Nearly every entrepreneur says that, when it comes to running a business, the highs are higher, and the lows are lower. A product doesn’t succeed, your product succeeds. On the flip side, the company doesn’t fail, your company fails. The stakes and stress are greater, but nothing would be worse for a serial entrepreneur than being an employee who could pass the blame up the ladder.
And, if things go well, the rewards are yours for the taking. Entrepreneur James Wong remembers a successful campaign as an accounting consultant. “Here we are working for our measly salary, and we just made half a million for the company. I figured if we went into our own business, we could do way better for ourselves.”
4. Risky Business(es)
If you stick a pro skier, kayaker, or mountain biker in an fMRI machine, you’d find numbed dopamine receptors; thus, these folks have to ski faster, drop bigger waterfalls, or jump gnarlier gaps just to get fired up. Stick a serial entrepreneur in an fMRI, and you’d find a similarly wired brain.
But instead of putting their lives on the line, entrepreneurs bet their livelihoods — money, relationships, and time.
“If you look at it realistically, the odds of success are really, really low,” Parker said. “The chance that we will succeed, continue to be friends, and make any money, is really low. If you were objective you would look at it and go, ‘This doesn’t make a lot of sense.’ But we look at the problem and think we can change the world. You have to be slightly delusional.”
That’s not to say these founders gravitate toward toxic propositions. The challenge for serial founders is to balance their slew of potentially ground-breaking ideas with what could feasibly work. They might be willing to take a risk by founding a company, but founding a company on a bad business plan puts family members and employees at risk, too.
“When I was younger, I was trying to prove to the world that I could be successful. I wanted to send message of, ‘Wow, look at me — I’m able to build a multimillion-dollar business,’” Wong said. “Now it’s more about, ‘Look what we’ve done for our employees, and look at what we’re doing for our society.’”
5. Wanting to win, and knowing you can
We’ve established serial entrepreneurs are constantly looking for business ideas, but turning a criticism into a company isn’t something that comes easily; there are plenty of times average people think somebody could make a lot of money building product X, but they lack the confidence to become that somebody.
Serial founders have one clear advantage when it comes to confidence: They’ve done it all before. Entrepreneurs must be confident running their first businesses, but having multiple successful exits — or multiple failures to learn from — breeds an understanding of how companies work and how a market need can be properly addressed.
“Ideas can sound great. It can be like, ‘Everyone needs one of these’ … but it may be the case that there really isn’t a business there,” Jesse said. “You have to have customers that are both willing to buy and able to buy.”
This confidence doesn’t exist in a vacuum. Just because an entrepreneur thinks he or she can do something better doesn’t mean the competition won’t change or materialize. When founding a company, serial entrepreneurs are confident that they understand a key element competitors don’t, and they’ll be able to adapt with the speed necessary to fend off other startups and deep-pocketed stalwarts alike.
“I’m very competitive. When I set out to do something, I work hard and I focus on improving myself constantly,” Muller said. “It’s no different than sports. You look at elite athletes — they’re super competitive, they’re very focused, they outwork, outsmart, and outmaneuver everyone else.”
6. Always on the Clock
Many of us work a lot, but compared with serial entrepreneurs, most people’s workweeks are a cakewalk. Founders are scrambling for funding, trying to release products, searching for the best workers, and are probably doing the work of an entire staff themselves.
This means long hours, but founders get to set those hours. Such is the strange dichotomy of running a company: Some folks founded companies because of their families. When you’re the boss, you don’t have to ask anyone if you can run your kid to the doctor or skip a day for your anniversary.
On the other hand, though, are later hours. Even if you can leave work in time to pick up your kids from school or be home for family dinners, that likely means you’ll have to work well into the night to make up for lost time.
“I get to decide which hours I work — which 12 hours of the day I work, that is,” Wong said. “But it’s not really working because I enjoy what I do.”
As with anyone, work-life balance is a juggling act. But entrepreneurs have more at stake — they don’t just have work tasks and home tasks. There are multiple tasks to monitor, employees to keep in line, and sometimes multiple companies to run. The professional demands can ratchet up the home demands, even with the added flexibility.
“You don’t have to be an entrepreneur to have the challenge of work-life balance, but that challenge is harder for an entrepreneur than anyone else,” Verschueren said.
7. Failure is an option
Products flop. Ideas don’t pan out. Hires turn toxic. Companies go bankrupt.
Most businesses fail, and for those that succeed, a panoply of elements of everyday operations falls flat on its face. Every failure can be traced back to a founder, especially in a small company.
But there’s no avoiding the screw-ups, so serial entrepreneurs learn to use the mishaps to their advantage.
“Something you learn as an entrepreneur is resiliency, and turning failures into learning experiences,” Verschueren said. “Sometimes people are serial entrepreneurs not because one startup is a huge success and they want more, but because one fizzles out and they just start again.”
Those who are able to turn mistakes into learning experiences often are those who don’t hold their own ideas sacred, and let the end user of their product or service determine what works and what doesn’t.
“Accept the fact that if you put something out there, and people don’t like it, that’s the stuff you listen to,” Drayton said. “Customers are smart as hell. I’ve had many of my favorite ideas crash and burn when we put it on the market, and that’s fine. Try it, and if it works, keep it. If it doesn’t work, try something else.”
Not only is Dave Parker helping people overhaul their careers at Code Fellows, he also serves on the board of directors for four companies, and formerly worked as the director of the Founders Institute and senior vice president at UP Global. Now, Parker is flexing his CEO muscles as Code Fellows embarks on a period of rapid growth. “It’s exciting because (we) already have the idea and its proven traction. It’s a super fun stage of business to be in,” Parker said.
Current gig: CEO of Code Fellows
Companies founded (eastside in bold): DKParker LLC, OneAccord Partners, Bundled.com, 9Spaces, License Online
Parting thought: “How I mitigate risk is totally different than first-time entrepreneurs. … As a repeat entrepreneur, you mitigate risks because you order priorities appropriately. You don’t have to build a product before you find out if the customer cares about what you’re doing. Prioritizing which questions you ask and when is the hard part, and part of that is learning through experience. But mentors and advisors can help with that.”
Serial entrepreneurs may start multiple companies, but few help run multiple companies simultaneously. That’s what Mary Jesse is up to, and she might be the busiest person on the list. Along with her professional juggling act, Jesse is a parent and mentors women in technology and business.
Current gigs: Executive at VRStudios, producer at Rip It Productions, president and COO of Photonic BioSystems, member of HipLink Software board of advisors, managing partner of Hexagon Blue
Companies founded: Rip It Productions, RadioFrame Networks, Ivycorp, Hexagon Blue
Parting thought: “I’m really quite adamant that company culture is incredibly important, because your employees really are your greatest assets and they’re the face to the customer. … The culture is modeled by the CEO and then cultivated within the company.”
Andy Sack worked on his first startup as a graduate student at MIT in the 1990s and hasn’t looked back. With Seattle’s Techstars, Sack used his fierce energy and impressive contact list to help other startups gain traction. Sack’s connection with Microsoft CEO Satya Nadella led to his most recent venture with fellow serial entrepreneur Philip Vaughn. Innovation Arts Group is working to help Microsoft become more agile by implementing practices utilized by startups. “It grew from a small consulting project to being rolled out across cloud and enterprise,” Sack said.
Current gig: Cofounder of Innovation Arts Group
Companies founded: Founders’ Co-op, Lighter Capital, Judy’s Book, Kefta, Abuzz, Firefly Network, Innovation Arts Group
Parting thought: “I write (ideas) down, and I don’t think any of the companies I’ve ever started have come from the notebook. It’s just an outlet for a nervous twitch.”
Sean Muller watched his father found and run a software company in Israel. That instilled in him the desire and expectation that he would lead a group, so as a student at the University of Washington, Muller decided to take his first crack at leadership by founding the school’s waterskiing team, which eventually climbed to No. 6 in the nation. After school, he jumped right into entrepreneurship and founded EduClick.
Current gig(s): CEO of iSpot.tv
Companies founded: EduClick, The Wedding Tracker, iSpot.tv
Parting thought: “You have to be honest with yourself about whether a product you’re developing is something the market needs. There’s a tendency to just convince yourself that a product is going to work out … that’s a mistake I learned from.”
Bellevue resident James Wong studied accounting at the University of Washington, but he always knew that he wanted to be an entrepreneur. His career took him to several major cities across the country, but he made his way back to the Eastside and Seattle to launch Avidian Technologies and his current company, SolTerra, an environmentally conscious development firm. Wong supports other entrepreneurs, too — he has dabbled in angel investing.
Current gigs: Chairman at Avidian Technologies, managing partner at SolTerra
Companies founded: Foci Technologies, Avidian Technologies, SolTerra
Parting thought: “Entrepreneurs are relentlessly resourceful. Every organization deals with limited resources, but entrepreneurs don’t let those limited resources stop them from moving forward.”
Joe Verschueren is a native of Mercer Island. After attending the University of Washington, Seattle University, and Gonzaga University, he launched his now long-term career in the tech industry. Since founding his first startup in 1992, Verschueren has never gone to work for anybody else.
Current gig(s): Executive vice president of business and development at Formotus
Companies founded: Parallel Communications, ImageX, Formotus
Parting thought: “The difference with startups is that you don’t have to love them equally like you do your kids. For example, I can definitely say Formotus is the one I’ve enjoyed the most, even with the stress of the recession and changes in the industry.”
Terry Drayton is best known for founding dot-com darling HomeGrocer.com, which eventually merged with, and floundered alongside, Webvan. But that’s not Drayton’s sole entrepreneurial venture. His first company sold bottled water, and he’s also run firms that handle online payments, storage rentals, and political social media.
Current gig: CEO of Livible
Companies founded: Laurentian Spring Valley, Aquaterra, HomeGrocer.com, Ramp Technology Group, Arena Group, Rainier Software, Votocracy, Storrage
Parting thought: “(Serial entrepreneurs are) chronic rule-breakers. We’re trying to figure out stuff, and we don’t care what the conventional wisdom is. We were always in trouble at school for asking the teacher, ‘Why?’ They’d say, ‘Go do this,’ and we’d say, ‘Why?’”
Marjorie Clark, Summer Meza, and Caroline Skinner contributed reporting to this article.
Photos by Rachel Coward
Note: This article originally was published in the September 2015 issue. It has been edited to reflect the updated names of SolTerra and Livible.