Why 4 Austin serial entrepreneurs keep coming back for more

Kelly Jackson

For entrepreneurs who have had a taste of success, founding one company is not always enough.

Neither is two, three, even four. But for serial entrepreneurs, what keeps driving this need?

We connected with four of Austin tech’s leading business leaders to discover what keeps them motivated as they launch venture after venture — and the lessons they’ve learned along the way.

 

Jan Ryan

With more than 25 years in the biz, Jan Ryan boasts quite a resume. While at Vignette Corporation, Ryan led the entire sales organization as VP until its IPO in 1999. She served as CEO at Sigma Dynamics, which Oracle acquired in 2006, and co-founded Social Dynamax in 2009 which Lithium Technologies acquired in 2012.

Today, Ryan supports the Austin startup community as a mentor, strategic advisor and angel investor, while leading [email protected], a women’s network to increase the number of women launched businesses locally. 

What drove you to start your next company after going through the process the first time?

Starting a company from an idea and building it up into something of value is very hard. I always say it’s the hardest thing you’ll ever love to do. It’s similar to an obsession. But somewhere through all the late nights and false starts and iterations and worries about capital you stop and realize that you and your team have created something that’s changed lives. What a rush!  Even after that right exit comes along who could resist doing it all over again, just to see if you could do it better and with half the mistakes?

What is the hardest lesson you’ve learned throughout your career?

I’d sum up everything I’ve learned with a mantra I often repeat with others: “Fall in love with making your customer’s lives better.” It’s so easy as an entrepreneur to get distracted by investors, or pitch events, or the dozens of issues you face in defining and running a new business. But I’ve learned the hard way that the customer’s voice is the only one that matters.  Let that be what wakes you up in the morning. Whether your skills are technical or customer facing, the reason you started the company is because you have an innate sense about what the customer needs and will buy. Stay faithful to that.

How does that lesson help you in running a company today?

I’m a believer in staying obsessively close to customer feedback and their evolving needs as you scale. For instance at Social Dynamx our product team spent a ton of time with our top customers. They were not only supporting the customer but watching how they used our product “in the wild” in their natural environments, and how we could make their lives easier. Likewise as sales teams scale, they should design the steps of their sales process and even their internal vocabulary to align with the customer’s buying processes, making it intuitive and easy to do business with you.  

What is the most valuable piece of advice you’ve received?

Get comfortable with uncertainty. My Dad used to model this in his own business. Entrepreneurs must be able to make a decision, any decision, and move on. New companies are loaded with risk — there are no sure bets — but if you take too long making decisions or waiting for the perfect moment, you’ll miss many of the best opportunities.


 

Sam Decker

It seems Sam Decker always had an itch for entrepreneurship. Before Clearhead and Mass Relevance, there was lawn mowing, neighborhood festivals and writing computer programs for his dad’s business. Today, Decker serves as executive chairman at Clearhead, chairman at Mashbox, executive advisor at Silvercar, a board member for Needle and mentor at Capital Factory

What drove you to start your next company after going through the process the first time?

Experience and confidence in what it takes to scale a company as well as understanding product/market fit and timing. Most of my early startup failures were due to bad timing and/or bad culture. Bazaarvoice, Mass Relevance and Clearhead were near perfect timing (and great culture).  

I also want to learn something new and building a company brings new experiences — which then leads to more confidence and so on. With each new company, repeating this cycle, you reduce risk. Reducing risk is an entrepreneur’s primary job, and it’s why investors back experienced entrepreneurs.

What is the hardest lesson you’ve learned throughout your career?

Delegation and sequencing. Entrepreneurs are Type A and competent (at least in their own head). But, they can’t do everything, nor should they. I once was behind the ball on hiring managers at Bazaarvoice. I learned that lesson and in the span of three months hired three competent executives at Mass Relevance at the right time.

You have to hire competent and passionate people and empower them to become entrepreneurs inside the company. A company is just systems and people interacting with each other. The core to reducing risk and growing a company is sequencing the hiring and launching of systems inside the company, delegating the creation of those systems and the execution of them.

How does that lesson help you in running a company today?

I’m chairman of a couple companies, which means I don’t run the show day to day. I’m active in highly leveraged ways but have been able to let go of decisions and know that the CEO and their teams are extremely capable of putting together the team and systems to grow the companies.

What is the most valuable piece of advice you’ve received?

Sometimes the advice that sticks wasn’t intended as advice at all. I worked with Manish Mehta at Dell and later hired him to run product at Mass Relevance (where he does at Spredfast today). Many years ago at Dell, I remember meeting him on some topic and he used the term “widen the aperture.” Obviously, there are a lot of corporate bingo phrases I’ve heard, and I don’t even remember the context of that comment. But “widen the aperture” is a phrase that has stuck with me as a reminder to think big, see the big picture, lead by helping others see that picture.


 

Vinay Bhagat

Eleven years after Vinay Bhagat founded Convio, a software platform for nonprofits, the company went public, having been sold for $325 million to Blackbaud. In 2012, Bhagat launched TrustRadius, an enterprise peer review platform for software solutions, where he serves as CEO. 

What drove you to start your next company after going through the process the first time?

I love building companies — finding unmet needs, defining solutions and assembling teams to solve the problem, and I am very proud of what we built at Convio. We helped bring the nonprofit sector into the digital age, raised billions of dollars for charity, became a public company and drove a healthy return for our investors. Yet I also felt there were things I could do much better second time around to build a more larger and more profitable business and to be more effective personally as an entrepreneur.

What is the hardest lesson you’ve learned throughout your career?

I started Convio in 1999, a time when capital was abundant. We raised A and B rounds quickly and spent them too quickly too by scaling our team ahead of market readiness. As a result, we had to do a reduction in force. And when markets turned south, we had to raise capital on unfavorable terms, which was very dilutive to the founders.

How does that lesson help you in running a company today?

While I have raised venture capital once again, we've been much more measured in our growth and kept our net burn rate low, enabling our capital to stretch. I believe that there are some problems which just take the time to solve and cannot be greatly accelerated by capital. Sometimes you need to walk slow to run fast later.

What is the most valuable piece of advice you’ve received?

Be intellectually honest. It's too easy to fall in love with your own ideas and believe your own projections. Listen to your customers, your team and your market.

 

Zeynep Young

Zeynep Young joined Next Coast Ventures this past March as the firm’s first venture partner. Young, who also serves as CEO of Austin spa Milk + Honey, previously founded Austin-based edtech company Double Line Partners and Data Narrative, a consulting company supporting the social sector. 

What drove you to start your next company after going through the process the first time?

I loved the feeling of coming up with a new idea and exploring a solution with customers. There's something really fun (terrifying but fun) about exploring a new product or a new way to do something.

What is the hardest lesson you’ve learned throughout your career?

Most people won't buy into your vision. Not every customer or investor will love your idea or believe in it. That doesn't mean it's not a good idea; it just may not be the right fit for that person.

How does that lesson help you in running a company today?

I've learned to not take "no" as personally. I try to learn from every interaction with a customer or investor. Even when the answer is no, you can learn a lot from the feedback and keep improving your concept.

What is the most valuable piece of advice you’ve received?

Always be selling. Some of my biggest opportunities came from informal conversations with acquaintances. You never know what connections people have.

 

Images have been provided by participants and social media.

What do you want to learn from Austin’s leading entrepreneurs? Let us know via our tip line or tweet us @BuiltInAustin

 

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