Adam Doppelt

Adam Doppelt

Current endeavor: founder, Dwellable
Prior companies founded or led: Urbanspoon, Strangeberry
Entrepreneurship advice: The best entrepreneurs refuse to give up, and simply barrel through any obstacles that arise. Cultivate persistence.

With his son

Andy Liu

Andy Liu

Current endeavor: CEO, Advanced Media Research Group (dba BuddyTV.com)
Prior companies founded or led: NetConversions
Entrepreneurship advice: A good plan violently executed today is far better than a perfect plan tomorrow. (George Patton)

At a technology lab focused on teaching technology and leadership skills in El Salvador

Andy Sack

Andy Sack

Current endeavor: general partner, Founders Co-op, Techstars Seattle, Code Fellows
Prior companies founded or led: Lighter Capital, Judy's Book, Kefta, Abuzz, Firefly Network
Entrepreneurship advice: Take more vacation. It'll help your career.

Sack

Ben Huh

Ben Huh

Current endeavor: founder and CEO, Cheezburger Inc.
Prior companies founded or led: Circa, Raydium
Entrepreneurship advice: Don't do what your advisors tell you, but be inspired by what they did and go find your own path.

Photo by John Keatly

Brenda Spoonemore

Brenda Spoonemore

Current endeavor: director, Kindle content, Amazon.com
Prior companies founded or led: Dwellable, Fantasy Moguls
Entrepreneurship advice: Share equity as equally as possible with your founding team and understand that key people coming into the company in the next 18 months may still need "founding team" treatment. It's a marathon, not a sprint. Keep everyone aligned on the fairness of the equity splits and you'll be better positioned for both success and tough times.

With her family

Bill Bryant

Bill Bryant

Current endeavor: venture partner, Draper Fisher Jurvetson, (based in London for a year)
Prior companies founded or led: Airworks, Medio, Mixxer, Qpass, Visio
Entrepreneurship advice: Startups are *way* hard. Success is a function of a multitude of factors coming together at a moment in time---unmet customer needs within an emerging market, a disruptive technology coupled with an innovative business model, a team that is made up of superstars as well as super contributors who are culturally cohesive and love working together, incredible strategic focus on a narrow set of objectives, forgiving competition who make strategic mistakes that you avoid, sustained hard work over a long arc, and more than a little luck.... Because it's hard, the emotional satisfaction when the team you’ve helped build and the culture you’ve helped create do experience success, it’s the greatest feeling in the world.

Brent Frei

Brent Frei

Current endeavor: executive chairman and co-founder, Smartsheet.com; founder, HarvestWest Investments
Prior companies founded or led: Onyx Software
Entrepreneurship advice: Put as much or more energy into selling and partnering as you put into creating your product. It'll make for better financial outcomes as well as better product.

With his family

Dan Shapiro

Dan Shapiro

Current endeavor: founder, Robot Turtles
Prior companies founded or led: Sparkbuy, Ontela
Entrepreneurship advice: When raising outside investment, you're constantly looking for feedback to tell you you're on the right track. What I've learned is that there's only one reliable indicator of progress: a cashed check. Everything else is noise.

Photo by Randy Stewart, blog.stewtopia.com. (CC)

David Bluhm

David Bluhm

Current endeavor: co-founder, chief marketing officer, Medio; co-founder, chairman CopsForHire
Prior companies founded or led: Z2, NextMedium, GoTV Networks, WUF Networks, HandsOn (aka (M)Forma), NearMe, 2WAY, Realtor.com, WorldVoice
Entrepreneurship advice: Be extremely selective when building your board.

Riding a trials bike in the woods

David Shim

David Shim

Current endeavor: founder and CEO, Placed
Prior companies founded or led: LeagueTraders, eccoBay.com
Entrepreneurship advice: Don’t talk, do. Great ideas and opportunities are rarely given to you, rather they require action to discover, shape, and execute against.

Jeremy Jaech

Jeremy Jaech

Current endeavor: CEO, SNUPI Technologies
Prior companies founded or led: Visio, Aldus, Verdiem, Trumba
Entrepreneurship advice: Persistence is the key. Nobody (including me) is irreplaceable. Surround yourself with people who are smarter than you. "Nothing in this world can take the place of persistence. Talent will not: nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not: the world is full of educated derelicts. Persistence and determination alone are omnipotent." (Calvin Coolidge)

With his wife Jacquelyn and their two dogs, Madeleine and Montgomery

Jonathan Sposato

Jonathan Sposato

Current endeavor: chairman of Geekwire, Vizify, and PicMonkey
Prior companies founded or led: Picnik.com, Phatbits
Entrepreneurship advice: This notion of 'screwing up fast'. I wish I had applied that same level of quickness in decision making earlier in my career, even when I was working at a big company, in order to increase the rapid pace of learning that occurs when you are willing to fail fast.

Kristen Hamilton

Kristen Hamilton

Current endeavor: co-founder and CEO, Kairos (working title only)
Prior companies founded or led: World Learning, Onvia
Entrepreneurship advice: Surround yourself with "co-CEOs", not just co-founders (colleagues, advisors, board members) who are better than you at something vitally important. Keep a beginner's mind and cultivate an environment that rewards you for being your best self. Fail fast, early and cheap.

Lisa Sharples

Lisa Sharples

Current endeavor: co-collaborator, Project Equator ("a family gap year")
Prior companies founded or led: Allrecipes.com, Garden.com
Entrepreneurship advice: Dozens of people will tell you why your idea isn't good. Don't let them deter you! The best entrepreneurs worked against all odds to create something others thought wasn't possible!

Sharples, second from left, with family in Oia, Greece

Michael

Michael "Luni" Libes

Current endeavor: founder and managing director of Fledge, Kick, and Realize Impact
Prior companies founded or led: Ground Truth, Medio Systems, 2WAY, Nimble Corp
Entrepreneurship advice: For most businesses, the outside funding entrepreneurs seek will do little more than speed the time to market, and the speed to failure or success. If there is a path to market with less money, it may take more time, but it avoids working for the investors' timeline instead of one's own.

On a road trip to Alaska

Mary Jesse

Mary Jesse

Current endeavor: founder and CEO, Ivycorp
Prior companies founded or led: Hexagon Blue Consulting, RadioFrame Networks
Entrepreneurship advice: A mentor taught me to “own their objections” when prepping to pitch an investor. This advice has been helpful in pitching, selling and even hiring. Prepare in advance to address potential issues head on in any discussion.

Mike Mathieu

Mike Mathieu

Current endeavor: founder and chairman, Front Seat
Prior companies founded or led: Walk Score, All Star Directories
Entrepreneurship advice: 1) Even if you're bootstrapping it's still better to have a board of directors; 2) The best entrepreneurs are those who are most aware of their own weaknesses; 3) Better to be a mediocre company in a growing market, than the best company in a declining market.

Mike McSherry

Mike McSherry

Current endeavor: VP, advertising and content, Nuance Communications
Prior companies founded or led: Swype, Amp'd Mobile, Boost Mobile Australia & US, Zivo Internet Services
Entrepreneurship advice: Trust serendipity. If you're smart, persistent and have your health, you'll always land on your feet. Every startup needs it's lucky break. But you create your own luck by being out there and trying.

Natalie Angelillo

Natalie Angelillo

Current endeavor: founder and CEO, SwopBoard
Prior companies founded or led: Swink Style Bar, Steelhead Group, PhotoZone.com
Entrepreneurship advice: Hire people smarter than you. Don't insist on being the CEO of your own idea.

Photo by Eva Blanchard

Oren Etzioni

Oren Etzioni

Current endeavor: executive director, Allen Institute for Artificial Intelligence
Prior companies founded or led: Decide, Farecast, Netbot, Clearforest
Entrepreneurship advice: The real risk is the risk of *not* doing a startup!

Finding cell coverage in Israel

Shwetak Patel

Shwetak Patel

Current endeavor: co-founder, SNUPI Technologies; associate professor, University of Washington
Prior companies founded or led: Zensi
Entrepreneurship advice: It's good to iterate fast on your project, but when it comes to business development you should focus focus focus and not bite off way too much.

With Jeff Bezos

Sunny Gupta

Sunny Gupta

Current endeavor: co-founder, president, and CEO, Apptio
Prior companies founded or led: Opsware, iConclude
Entrepreneurship advice: Don’t get too stuck on your original idea—it’ll morph like 50 times as you bring it to market. We once thought Apptio would be a transactional play, like a ten- or fifteen-thousand-dollar sale to director-level people. As we validated the idea, we found out it’s a strategic sale much higher up in the organization. Be open to change.

T.A. McCann

T.A. McCann

Current endeavor: co-founder, RivalIQ
Prior companies founded or led: Gist.com, Jump2Go
Entrepreneurship advice: 1) Always be recruiting. Finding the best people takes a long time and you need to be building relationships with top performers well before you might need them. 2) Don't just sell your stuff, advocate for the customer. With each meeting, give them more value than they give you, usually in the form of suggestions of products, services or approaches which can improve their overall business/success.

Swimming with jellyfish in Borneo

Thor Culverhouse

Thor Culverhouse

Current endeavor: CEO, Skytap
Prior companies founded or led: Stratavia, willbeHired
Entrepreneurship advice: Ideas are great, but without a great team that can execute, and ongoing access to capital, you are nothing.

With his family

Tom Huseby

Tom Huseby

Current endeavor: managing partner, SeaPoint Ventures; venture partner, Voyager Capital
Prior companies founded or led: Metawave Communications, Innova, Tegic, Snapin
Entrepreneurship advice: Most startups don't fail because they can't make the product. They fail because nobody wants the product.

Villette Nolon

Villette Nolon

Current endeavor: consulting, Angel Capital Association
Prior companies founded or led: HomeSavvi, NetReflector, Ameriscribe Data Resources
Entrepreneurship advice: Assemble the absolute best team possible. The quality of that team will be the most important predictor of success.

What does it take to make it as a startup entrepreneur? Persistence and a great team.

Those themes came up repeatedly when we asked 26 serial entrepreneurs in the Seattle technology industry for the entrepreneurship advice they wish they’d heard earlier in their careers. We’ve collected their words of wisdom—as well as pictures of the entrepreneurs having fun and with their families—in the slideshow above.

We consulted with venture capitalists, angel investors, and others in the Seattle tech entrepreneurship community to identify this group of repeat hit-makers. But we know there are more out there, and we’d love to hear from readers about the ones we missed. We plan to update this list with your suggestions, and to recognize future successes.

Our imperfect definition of “serial entrepreneur” is someone who has founded more than one tech company, or founded one and held a C-level or equivalent position at another. Our list includes some people who are now primarily investors. And it leaves off some iconic founders who have reached global-scale levels of success—and are therefore rather hard to contact—or have so far only done one startup. Names like Bezos and Gates and Rich Barton come to mind for the former group, and Sujal Patel of Isilon Systems and Kabir Shahani of Appature for the latter.

We hope this collection of entrepreneurship advice will add inspiration as Seattle pays extra attention to startups and innovation this month. Events include Entrepreneur Week 2013, going on now on the University of Washington campus; Northwest Entrepreneur Network’s Entrepreneur University 2013 on Friday; and Seattle Startup Week, Oct. 18-25, with a ton of great events such as Techstars Demo Day on Thursday, Oct. 24, and Geekwire’s Startup Day on Friday, Oct. 25.

Benjamin Romano is editor of Xconomy Seattle. Email him at bromano [at] xconomy.com.

  • Danielanthony

    nice collection

  • http://www.blackhawkpartners.com/ Ziad K Abdelnour

    entrepreneurs are people who, starting with nothing more than an idea
    for a new venture, have the ability to take it to the point at which the
    business can sustain itself on its own internally generated cash flow.

    Thank you.