Ep. 67 - Evolution of Entrepreneurship: Perceptions, Realities and Finding the All-Important Truths - with Bryan Stolle
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Being an entrepreneur is one of the most challenging career paths you can take — something that Bryan Stolle, serial entrepreneur and Founding Partner at Wildcat Venture Partners, knows intimately. Entrepreneurial success stories have become so pervasive in our culture that it may seem like the easy way out, but don’t let the hype fool you.
Between the draw of Silicon Valley and the success of shows like Shark Tank, entrepreneurship and startups are undoubtedly more trendy than ever. In some ways, it’s become an obsession.
Some view entrepreneurship as an outcome, while others see it as a necessity, or even as a habit and a practice. Technology has also seemingly made it easier to achieve success. But is that really the case?
To answer that question, we sit down with Bryan Stolle, who has created more than $1 billion in realized liquidity for his investors as a founder of multiple companies. And as founder and CEO of Agile Software, Bryan led the creation of a new category now called product lifecycle management (PLM).
In this episode, Bryan shares his perspective on:
The perceptions and realities of entrepreneurship and its evolution
The myths and misconceptions that are still are prevalent
What an aspiring or current entrepreneur needs to consider to create momentum for success
Wired for Entrepreneurship
Having two generations of self-made businessmen in the family exposed Bryan early to the realities of entrepreneurship. His grandfather owned the first Ford tractor dealership in South Central Texas and was involved with real estate.
His father not only worked for large companies in his career but also pursued several entrepreneurial ventures. And while Bryan saw that his dad was happier doing his various startups, Bryan recognized that this freedom came with a different level of responsibility and tradeoffs.
Bryan also had a love for science fiction as a child and teen that enabled him to envision the future from multiple perspectives—not only from a technology lens but also from a societal structures and cultures point of view. This, along with the fact that he lived overseas in multiple third-world countries as a young oil brat, helped him establish a more open-minded view of the world.
Bryan was a self-proclaimed gadget-geek as well. This passion led him to motorcycles and eventually racing professionally at the age of 17. He took on every technical and business aspect of the sport, as he had to learn how to manage and fund the venture on his own. This early entrepreneurial experience taught him about the level of discipline, focus, and sacrifice needed in order to make it.
But he realized that his generalized ambitions weren’t going to be fulfilled without a college degree, and pursuing racing and academic paths simultaneously wasn’t going to be possible. So Bryan pursued a business degree and, after college, he spent time working for Electronic Data Systems, where he was able to jump head-first into the rapidly evolving world of technology.
While Bryan’s time at EDS was invaluable, he had no interest in climbing the corporate ladder the same old way. He always knew he wanted to start a company someday. After getting his MBA, he happened to fortuitously enter the world of startups, and those experiences gave him the opportunity to expand his roles and responsibilities and gain exposure to the entire workings of a company. And since he had always reported either directly or indirectly to CEOs, he also got to observe the good, the bad, and the ugly.
Bryan learned a lot of lessons — both strategic and operational — around what to do and what not to do, the right way to go to market, and the right way to organize for customer success. These lessons lead him down the path of success when he set out to create his own company Agile Software, and it’s these same insights he shares with the founders of companies he invests in as a venture capitalist.
The Evolution of Entrepreneurship: What Has and Hasn’t Changed
Despite the hype, coolness factor, and perceptions of immediate fame and fortune around entrepreneurship that exists today, the reality is that entrepreneurship now is really no different than it was 50 years ago. It is still a long arduous journey because, as Bryan shares, “It’s a completely irrational act to start a company. The odds are completely against you.”
The fundamentals are still the fundamentals; but now, speed to market is more important than ever.
An entrepreneur still sees how a problem can be solved differently and views it with a different level of risk compared to others, is willing to do “unnatural” acts to solve that problem, and is willing to make sacrifices.
Yet, to realize this vision, one has to be a great leader and promoter who gets other people on board who are equally willing to do those unnatural acts. You have to be a great team-builder with a clear definition of culture and how they want to operate, and then hire only people who align to those principles as they build and scale.
Always Ask and Understand the “Why” to Get to the Truth
To be successful as an entrepreneur, it’s still about the customer, first and foremost. You have to understand what they want, what they need, and what they are willing to accept. And to do this, you need to be a voracious learner, always ask “why,” then listen, analyze and really absorb the feedback. These aspects of entrepreneurship will always be consistent. It’s what that learning is and how you apply it that really shapes your trajectory to finding that truth.
So you have to be agile and pivot based on what your data and insights tell you. Keep up with what can impact your customers, your business and industry. And most importantly, you have to be able to build and lead a team that is just as invested as you are — because, ultimately, no one can do it alone.
Bryan’s Career Advice
As a leader, it’s critical to continually assess your team and understand where they are. Often, by the time you realize someone is not the right fit for the job, you’re already six months late.
You should absolutely respect and reward employee loyalty, but it doesn't have to be by giving someone more and more responsibility they can't handle.
Get more leadership and management experience earlier. At the end of the day, nothing happens without a team of people, so becoming as good as you can be at leading and managing as early as possible is great.
Key Takeaways:
Perceptions/Myths, Definition, Mindset
There is no such thing as instant success, despite the idealization of entrepreneurship in the news media.
To be an entrepreneur, you have to make sacrifices that most human beings are not willing to make. Often, people don’t realize how hard it really is and how much sacrifice has to be made.
There is tremendous value in creating new categories, but it is extremely difficult. The world doesn’t want something new by default. So you have to think about what you're willing to sacrifice to break through.
To build a great company, the focus has to be about building something great and lasting vs. fame and fortune.
Almost any great company that's been built has been built on the back of a tremendous amount of prior knowledge and experience that, finally, was applied to a problem in a different way.
Success Factors
As an entrepreneur, you need to find people who are all equally irrational and equally willing to do unnatural acts to make something happen.
There's no company that's ever been created that didn't take a team of people working together to make it happen.
Everyone you bring also has to think like a business owner. They need to take responsibility and accountability for the organization they're in, regardless of what position they have. They are responsible for the culture just like anyone else.
Be a great team builder. That starts with having a very clear idea about what kind of culture you're going to have, how the company is going to operate and behave, and then, hiring people who are going to embrace that and are going to go behave and act that way.
It all starts and ends with the customer. You constantly need to be a voracious learner and always ask “why?” to understand them.
Keep up with the constantly evolving market, competitive, and customer dynamics. Your relevance and ongoing competitive viability depends on it.
Success comes from having a blend of “really good data and really good insights.” Those insights are fueled by the data but still involve intuition to put it all together. The best entrepreneurs are those who can synthesize all of the data and put it together.
In today’s world of machine learning and AI, the data is more expansive and available. So you now have the ability to rapidly experiment, learn and optimize your product or service.
The more questions you can ask the better. “If you ask the right thousand questions, you're going to get much, much further than if you asked a hundred.” Try to understand the difference between what people say they want and what they'll actually do.
Learning means listening, which entails absorbing the constructive feedback that may be provided in order to move forward.
It's not about your ideas being trashed. It's about finding the truth, finding out what the market really needs and wants and what the market's willing to accept. It’s finding that market-product fit.
“Why” is so fundamentally important to business success. If you embrace “why,” not in a confrontational way but in a “I want to understand so I can do a better job” way, you are going to be much more effective.
