skip to Main Content

What I’ve Learned in 10 Years as an Entrepreneur (Thinks Out Loud Episode 322)

What I've Learned in 10 Year as an Entrepreneur: Team brainstorming ideas

I started my company ten years ago this month. And, that’s got me thinking a fair bit about what I’ve learned in the last 10 years as an entrepreneur. While some of these lessons are things you probably already know — or that I knew — what the last decade has driven home is how important these particular lessons are. It’s not that any one of these is earth-shattering. In fact, they’re fairly foundational. But what they all share in common is that, in a world where we’re facing dramatic change every single day, it’s even more important that we keep our foundation stable. We can’t adapt to the world around us if the ground is crumbling beneath our feet. And when you put these lessons together for your business, you’ll find the firmest ground you can stand on. And the greatest benefit for the long term.

The latest episode of Thinks Out Loud looks at lessons I’ve learned in 10 years as an entrepreneur. And, hopefully, they’ll help you learn how you can succeed for the next ten years… and beyond.

Want to learn more? Here are the show notes for you.

Thinks Out Loud Episode 322: What I’ve Learned in 10 Years as an Entrepreneur Headlines and Show Notes

Show Notes and Links

As always, here are the "regular" show notes, detailing links and news related to this week’s episode. Take note, there are a lot of links this week based on the wide-ranging discussion. Be sure to check out all those that matter for your business once you’ve given the episode a listen.

Free Downloads

We have a couple of free downloads for you to help you navigate the current situation, which you can find right here:

Thinks Out Loud is sponsored by SoloSegment: SoloSegment increases large-enterprise, B2B website conversion with easy-to-install software that automatically connects website visitors to the content they need to see to achieve their goals. SoloSegment does this using anonymous data and machine learning ensuring privacy compliance, addressing the many anonymous visitors, and improving the efficiency of marketing teams. Visit

Subscribe to Thinks Out Loud

Contact information for the podcast:

Past Insights from Tim Peter Thinks

You might also want to check out these slides I had the pleasure of presenting recently about the key trends shaping marketing in the next year. Here are the slides for your reference:

Technical Details for Thinks Out Loud

Recorded using a Heil PR-40 Dynamic Studio Recording Mic and a Focusrite Scarlett 4i4 (3rd Gen) USB Audio Interface into Logic Pro X for the Mac.

Running time: 21m 41s

You can subscribe to Thinks Out Loud in iTunes, the Google Play Store, via our dedicated podcast RSS feed (or sign up for our free newsletter). You can also download/listen to the podcast here on Thinks using the player at the top of this page.

Transcript: What I’ve Learned in 10 Years as an Entrepreneur

Well, hello again, everyone, and welcome back to Thinks Out Loud, your source for all the digital marketing expertise your business needs. My name is Tim Peter. This is episode 322 of the big show.

And I think we have a really interesting show for you today. It’s a little bit different, and I’m going to tell you right up front it’s a little more unusual than the ones we normally do here… because we’re so normal anyway. But I’m in a bit of a contemplative mood. I am coming up on 10 years of having my consultancy, 10 years since Tim Peter & Associates started. I’ve also been an entrepreneur involved with a software startup, SoloSegment, you know them. I’ve talked about them before, for, oh my gosh, almost five years now, a little over four years. And I’m in a place where I’m looking back on what has worked, what hasn’t worked, what have I learned?

I thought it might be interesting to share some of that with you. Some of these are things that I’ve learned in the last 10 years. Some of these are things I’ve learned in the last five years. Some of these are things I’ve learned in the last 10 or 20-plus years of my career. But they’re all things that I think are valuable as you look at, not just where we’ve been — I’m not a big fan of spending time looking back too much other than to understand what could we do differently? What could we do better? What can we learn? — I am, as you well know, really fond of looking forward. "What are the trends? What are the places where we’re going?" to help think about what you need to do next.

###Time Is Always Your Most Precious Asset
Some of these are things you’ve probably heard before. Some of these are things that you probably know. I just thought they might be interesting to help you figure out, okay, what do we do going forward? The first big one, and it’s probably the single biggest one, is that time is your most precious asset. Now, before everybody goes, "Well, duh," and just immediately turns this off, you probably know that, but I want you to think about if you know that, what are you doing because of that?

The Pace of Change Ain’t Slowing Down Anytime Soon

We live in an era of continual and rapid change, and that’s not going to slow down. You’ve heard me talk about many times, and it’s one of the things I think I’ve really taken to heart over the time that I’ve been running my own business, is that the Jeff Bezos thing of what doesn’t change. Don’t focus on the things that will change, focus on the things that won’t change.

It seems unlikely that we’re going to see the pace of change slow down. It seems unlikely that we’re going to see the amount of transition and transformation and disruption slow down. If we know that things are going to continually accelerate, our ability to be aware of our time and where we put our efforts and where we put our focus, just becomes that much more important, just becomes that much more critical to doing what we do, whether you are a business leader, whether you are the head of marketing, whether you’re a marketing manager, whether you’re a startup, whether you’re an entrepreneur. It doesn’t matter what your role is, you’re going to find yourself in a position to say, "I have to adapt to this."

How Can You Slow Down Your Perception?

The first thing that I try to do is, I try to slow things down. If you’ve ever heard, and I apologize for the sports analogy, but if you’ve ever heard older athletes talk about how they see the games that they play — you often hear this from quarterbacks in football, or you hear this from really great hitters in baseball. I’m sure you see this in other sports, too — but they talk about the fact that the game got slow for them (to a certain point obviously). If you’re a pro athlete and you get old, just because you can see it more slowly doesn’t mean that you can pull it off. But hopefully none of us have that problem.

It’s this idea where you’re trying to see the game more slowly. And there’s a bunch of tools that I use, that others use, to do this.

Circles, Squares, and Triangles: The Power of Frameworks

Every consultant in the world is fond of frameworks. I always refer to them as "Circles, Squares, and Triangles." You want to systemize your thinking wherever you can. I call them "Circles, Squares, and Triangles" because if you think about any framework you’ve ever seen, that’s how they tend to be presented. They tend to be presented as a circle. They tend to be presented as a square; just think of the BCG 2×2 matrix. They seem to be presented as triangles.

Applying Frameworks in the Real World

And you’re looking at how you apply these in the world around you, how do they help you see the world more slowly so that you can look at what’s going on rather than just everything rushing at you all at once. They can provide you clarity. They can provide you insight.

Break Out of the Box: Recognize Frameworks Limitations

What you also have to do is recognize their limits. Where you see people who consult or you see business executives, or you see business leaders go wrong, is they say, "Oh, I know what this looks like, because I can fit it into the square that I am comfortable with. I can fit it into the circle I’m comfortable with." By the way, I’m going to link to some of the frameworks that I like in the show notes. But the idea is, you can get… Pardon the phrase, but too inside the box.

So you should always be looking when you’re applying the framework for the evidence and the items that break the framework. Frameworks work best when you’re using them in a scientific way. What’s your hypothesis about what the framework is, and then look for data that proves that hypothesis wrong. If you can’t find it, then that suggests it doesn’t prove, but it suggests that the hypothesis might be right and that the framework is going to fit. But the idea isn’t go in, take a framework and say, "I’m going to shove this square peg into a round hole, or this round peg into a square hole".

It’s, "what doesn’t fit about this?" And that’s where the interesting part comes in, because that’s what starts to tell you, okay, here’s how we have to look at this differently. It helps you focus your attention. Because if everything does fit, the framework fits, just deal with it.

Everything that’s around it, everything that’s outside it, that’s the stuff you have to say, "OK, either the framework is incorrect because what’s inside mostly doesn’t fit. Or the framework works, but there’s some things around the edges that maybe we need to look at a little more closely." And it allows you to focus your time more effectively, be able to see the bigger picture more effectively and slow down the pace of change a little more effectively.

My Favorite Strategy Framework

I do the same thing. I’ll tell you about a couple of frameworks I really like. One is the way I think about the strategy. You’ve heard me say this a ton of times. This came from a book called "Being Strategic" by Erika Andersen. It’s a great book. I highly recommend it.

You think in terms of:

  • What is the hope? What are you trying to get to?
  • Where are you now? Taking a really clear, crystal clear look, at the reality of your current situation. Because you’ll never figure out how to get where you’re going if you don’t know where you’re starting from.
  • You then need to look at what are the walls, what are the things that get in the way between where you are and where you’re trying to go?
  • And then what’s your plan?

If you know where you’re trying to go, if you know where you are, if you understand what’s in the way, what’s your plan to move forward? How do you get around or over or through those walls? How do you execute on the strategy you’ve put together? Because execution matters as much as the strategy itself. How are you moving towards the goals you’ve set for yourself, the hope that you’ve set for yourself?

Execute Against Your Plan

I will tell you one of the places that I think people go wrong on execution, one of the places I’ve gone wrong when it comes to execution, is that when we think about the hope, sometimes we’re not thinking about where we really want to get to clearly.

If we’re acting strategically, if we’re thinking strategically, what it really means is that, and, again, this is from Erika Andersen — I just think this is such a great way to think about it — It’s that we’re consistently taking the actions and making the core directional decisions that move us towards some hoped-for future. So when you think about your hoped-for future, what are you really thinking about?

Top 5 vs. the Next 20: Be Clear on Your Goals

There’s a great model I love. This comes from Warren Buffett, where he talks about the fact that you really need to make a list of your top five objectives, the top five things that are the most important to you. And then you should make a list of the next 20 things that are important to you. What’s important to you that you want to accomplish there?

And you should split that list into two, the five top things and the other 20. And then your job, your purpose, your intent needs to be to avoid those other 20 at all costs. Because those 20 will distract you from the things you said are the five most important things to you.

If you’re focused on those five top things, or if you’re saying those top five things are the most important to you, and then you’re spending time on the other 20, you’re really not doing the things that are going to move you towards your hoped-for future. So it’s a really valuable way to think about where am I trying to get, and am I doing the right things? Because if you don’t execute, you’re not going to achieve your objectives.

Give Time to Your Most Important Goals

As you look at your top five items, what are you doing each day, each week, each month to move you towards those goals? If not, why not? Those are additional walls. Those are additional obstacles that you need to think about.

Take a look at whether those encompass all the areas of your life. Are you thinking about just your career? Are you thinking about just your finances? Are you also thinking about your family and friends? Your health, and these days I think we’ve all learned we mean both mental as well as physical health. Are you thinking about how to build the kind of life that you want to have, the kind of life that you want to lead, the kind of places that you want to get to?

Build Feedback into the Process

How frequently do you assess the progress that you’re making? And make sure you have some feedback around this, whether it comes from other people or whether you’re doing it yourself, from a self-reflection point of view. Think about it monthly, think about it quarterly, think about it annually, and give yourself feedback.

This Isn’t "Pass/Fail"

Get feedback from others. Don’t think about it in terms of passing or failing. I’m a big believer in school. I’m a big believer in education. I teach at Rutgers Business School’s Exec Ed programs. I’m a huge believer in education.

One of the big harms of education, though, is it has taught us throughout our lives to think in terms of passing and failing. This is life. This is business. You’re not passing or failing. You’re either making progress towards where you’re trying to get to, or you’re suffering from some setbacks at the moment. But those setbacks are only temporary. There’s no end of term, and then you get held back or anything like that. There’s no end of the marking period and you’ve got to take the class again.

It’s "you took the class, you learned some stuff, how do you apply the learning?" Think in terms of what do I need to improve? How can you improve? How can you do better? You didn’t fail, you learned something. And now how do you apply those learnings? One of the best pieces of advice I ever got was, and I’ve told this story a couple of times before, but I was involved in a big project at my work that went horribly wrong, really, really bad, years ago. This was, gosh, 15 years ago. Afterwards, I was having a conversation with my boss and he brought it up. I said, "Can you do me a favor? Can we never talk about that again?"

He said, "Here’s the thing. You paid the tuition. You may as well apply the learning." And I thought that was a really smart way of looking at it, and something I try to apply. So you’re not thinking in terms of passing or failing, you’re not thinking "I got an A," "I got a B," "I got a C," "I got a D." You’re thinking in terms of, "Great, what have I learned? What do I do to improve based on those learnings?"

Improve Where You Do Well, Too

And that’s just as true for where you’re making progress as where you’re not making progress. How can you improve on the things? How can you double-down on the things that have been successful for you, that have been useful for you? Because that’s how you’re going to get to a better place all the way around.

Your Team is Everything

The last thing that I want to talk about, and this is something that was hard for me to learn personally, has been very hard for me to learn throughout my career. It’s a weird admission, but we fall into something that can be called "success patterns." Same boss, by the way, the same mentor as the earlier story always talked about this idea of our greatest strengths can be our greatest weaknesses. But we get into a pattern. We succeeded because of X and thus we assume that X will always serve us in every scenario, just like the frameworks I talked about before. A big part of my success throughout my career was learning how to do stuff quickly and translating it for others. There’s probably a reason I got into consulting and teaching and things like that as a living.

But, of course, the thing that you always have to remember, and I’m saying this for me as much as you, is a lot of your success depends as much on the people you surround yourself with. I’m not telling you anything you don’t know, but it’s not about me. It’s about the team that supports me. It’s about the people that sustain me in my life. And I include in that, not just the folks on my team and not just the folks that I work with, but the many, many, many mentors who have been so valuable to my learning and to my growth over the last four years, over the last 10 years, over the last 25 years.

My Clients Are on the Team, Too

It includes my clients. I am blessed to have the best clients in the world, and I get to work with some of the coolest people you could possibly imagine.

I learn from all of these folks every day, I get better at what I do because of these folks every single day. You want to make better use of your time? Figure out how to get other people to teach you constantly, because you’re going to be better for it. You’re going to be richer for it. You’re going to be more fulfilled for it. And you’re going to find that everything else doesn’t matter as much as the people we surround ourselves with.

A Moment of Gratitude

I just want to say that I am the luckiest person in the world to have these people in my life, and I learn from them every single day. Not just about business, not just about work, not just about news, or things like that, but about life and about myself. They help me grow. They help me be a better person. For that, I am so very, very grateful.

I’m also very grateful for you. I talk about this a lot, but I do the show, at least in part, for me as well as you. I enjoy it. It gives me a chance to, as the title goes, think out loud. It gives me a chance to think about what’s important and what I need to focus on so that I’m focused on the top five things I am trying to accomplish. The fact that you tune in, the fact that you’re here, the fact that you listen, the fact that you comment, the fact that you share, the fact that you email me and Tweet and all of the other things that you do, is so wonderful to me. I would not do this show without you. I really am so appreciative for the fact that you have supported everything that I do for so long, and I just wanted to say thanks for that.

Show Closing and Credits

With that, we are out of time. I really want to say thanks again for all that you do. I genuinely, genuinely appreciate it. I’m going to skip with our regular credits this time. I just want to give you the quick reminder, you can find the show at You can find us at Spotify. You can find us on Stitcher Radio or Google Podcasts or Apple Podcasts or wherever you want to find the show. But if you’d go ahead and click on the subscribe button or click on the share button or click on the comment button and give us some feedback, I’d really appreciate it.

If I can help you in any way, feel free to shoot me an email at Feel free to hit me up on Twitter, using the Twitter handle @TC Peter. You can find me on Facebook or LinkedIn using, the URL is or

With that, I hope you take care of yourself. I hope you stay well. I hope you stay healthy. I’m looking forward to continuing the dialogue for the next X number of years, 5, 10, 15, who can say? But I really do appreciate the fact that you’re here. I’ll look forward to speaking with you here on Thinks Out Loud next week. Until then, please be well, be safe, and as ever, take care, everybody.

Tim Peter is the founder and president of Tim Peter & Associates. You can learn more about our company's strategy and digital marketing consulting services here or about Tim here.

This Post Has 0 Comments

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Back To Top