8 Business Exits by 35! Uncover the Secrets of a Serial Entrepreneur – Travis Steffen

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Show Notes:

Business growth never happens in a straight line. So take it one step at a time and learn from seasoned entrepreneurs who have been through the reps. Our guest’s inspiring story will help set you up for success and growth!

Meet Travis Steffen. Travis is a Serial Founder with eight business exits so far, and he’s only 35! Over the past 14 years, he has successfully built, scaled, and sold eight companies, both venture-backed and bootstrapped. He’s also raised over $100m in capital and has created over $750m in enterprise value. Now he’s committed to mentoring other motivated entrepreneurs to do the same. Travis is a growth mentor for Silicon Valley’s top accelerators, who’s been featured in the majority of the most renowned business publications.

A doctoral candidate in marketing with a specialization in AI and a published book author, Travis is the go-to person for all things entrepreneurship, AI, and growth.

In this episode of the Think Business with Tyler podcast, we talk about why everyone’s journey to entrepreneurship is different, the importance of taking calculated risks, why it’s critical to leverage artificial intelligence in business, and how to unlink your self-worth from your company.

If you want to hear more about accelerated growth and success in business, make sure you tune into this episode to hear what Travis has to say.


💡 Name: Travis Steffen

💡 What he does: He is currently the CEO of GrowthTeam and Founder of High Growth Leaders.

💡 Noteworthy: Travis is a serial founder with eight business exits. He’s also a bestselling author and an inspiring growth mentor.

💡 Key Quote: “Your self-worth as a human is not equivalent to the numbers in your bank account. I think oftentimes the things that we as humans do in our lives are oftentimes like to be seen as something.”

💡 Where to find Travis: LinkedIn

Key Insights

Everyone’s entrepreneurial journey is different. The journey to building a successful business looks different for everyone. So even though you should learn from other experts along the way, you’re the only one who knows what’s really best for your business. Travis shares his experience. He says, “I didn’t have any role models in entrepreneurship. I didn’t have anything like that. I didn’t have an education even after my first master’s degree. I didn’t have an education in entrepreneurship, but I was interested in finding something to do where I wasn’t working for somebody that I didn’t respect. And that was really my only path at that age because I didn’t really have any skills so I had to read a lot, ask a lot of questions online.”

Take calculated risks in business. There’s no success in business without an occasional risk. So, if you want to build a strong and successful business, you need to be prepared to take some risks from time to time. But make sure you do your best to minimize the negative outcomes and maximize the positive ones. Travis says, “For me now, in ventures, I’m always looking for ways to reduce risk without reducing the potential upside, kind of like they would do in quantitative trading or hedge funds. You do want a little bit of a hedge against downside. You want downside protection, but you don’t want to cap your upside if you can help it. So that’s kind of how I think about entrepreneurship a little bit more now where, how can I make sure I am validating as much as I possibly can before I invest into a company that I’m building personally without missing the opportunity window.”

Get on board the AI train. AI is here to stay, there’s no doubt about that. So as a business owner, you need to get on board it as soon as possible. Otherwise, you will get crushed by the competition. Travis explains, “As a business owner, you’re either going to be on a quest to thicken your margin or increase your production, right? 1 of those 2 is probably going to be the case. And AI can do both of those for you. […] If your company is not doing well and you have to cut expenses to stay alive, it’s likely that with the use of AI, you can cut staff, which is going to be one of your biggest expenses, without cutting production capacity because you can amplify the production ability of those that are still employed.”

Unlink your self-worth from your business. When you’re a long-time entrepreneur, your business becomes you, and you become your business. Not that there’s anything bad with being attached to your business, but you shouldn’t tie your self-worth to the success of your company. Travis says, “Your self-worth as a human is not equivalent to the numbers in your bank account. I think oftentimes the things that we as humans do in our lives are oftentimes like to be seen as something. […] “I think it’s useful to ask yourself why you’re doing some of the things that you’re doing, and if the answer is like, I want to be seen as successful, important, significant, et cetera, that’s a barrier that you can cross in ways other than busting your butt for 5, 10, 20 years, doing things that cause you to miss out on that 5, 10, 20-year stretch.”

Top Quotes

“Dan Caldwell was saying that he was looking at someone successful that he knew, and he was looking at them being like, ‘One day, one day, one day.’ And that started being my mantra about those guys.”

“The lesson that it taught me was like, you can build anything, but it doesn’t mean that people are actually going to use it. So that’s when I started to kind of round out my skillset more entrepreneurially.”

“That’s kind of how I think about entrepreneurship a little bit more now where how can I make sure I am validating as much as I possibly can before I invest into a company that I’m building personally without missing the opportunity window.”

“At the end of the day, if you wait for a hundred percent of information, you’re acting too late. If you wait for 50% of the information, you might as well flip a coin. A kind of sweet spot in there is like 70, 75%, so you want as much as you can get to arm you with as much information as you can to make the best decisions that you can make, and that’s what it is. And sometimes the probability will catch up to you, and you’ll lose, but if you practice good bankroll management again, using that same tenant, and you practice good risk management, by and large, you’re going to come out ahead.”

“It’s here. There’s not much to say other than you’ve got to either get on the train or get run over by it. It’s a pretty fascinating piece of technology that’s been conceptualized for the last 80 years. We haven’t had the computing power until recently to really make it work well in its current form, but we’ve been using AI as consumers for the last 30 years, like without really knowing it.”

“This is a tool that exists today. It’s at your fingertips. If you’re not using every resource available, your competitors will, and that’s just where you’re at now. If that’s how we all go down, it’s all how we all go down. We might as well use every tool at our disposal to create as much value for other humans as we possibly can.”

“There are some people who are just pathologically in a quest for more. It’s not the gift that a lot of people think it is. And I’ve been that person before. You will wake up at some point and recognize that you’ve been missing out and lit a chunk of your life on fire as a result. So do the things that are really interesting for you, solve problems that are really fulfilling to solve every day. But time box the things that you’re doing so that you can actually go out and live other aspects of your life.”

“If you’re going to do something professionally, try to inspire people, try to help people try to add value to people, do things that you’d be proud of having done if you’re in your final moments.”


Eliezer Yudkowsky: Dangers of AI and the End of Human Civilization

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