27 Actionable Insights I Learned From Interviewing 100 Entrepreneurs

27 Actionable Insights I Learned From Interviewing 100 Entrepreneurs
What I learned from interviewing 100 entrepreneurs that you can take action on today.

I’m pretty darn proud of the fact that I have released 100 episodes with all sorts of entrepreneurs with the goal to help build a more ethical, inclusive, and resilient world by educating and inspiring the next generation of entrepreneurs.

I know that may sound like a bold, almost crazy goal, but if you’re going to do something, it might as well be bold and crazy. I mean, it is a podcast about being an entrepreneur.

On the surface, a podcast does not seem like a bold and crazy endeavor. What is bold and crazy is to continue to do it, week after week, to improve oneself in the art of conversation, networking, and acquiring wisdom. That’s what I have gotten out of these interviews and I wanted to do this bonus episode to tell you what I have learned. Before we do that, let me tell you about how it all started.

A Little Bit of Background

The Entrepreneur Ethos Podcast was inspired by the book of the same name that I published in 2017. That book, in turn, was inspired by two events that changed the course of my life forever -- meeting a girl and getting accepted into an accelerator because of said girl. The girl was my late wife Jane and the accelerator was 500 Startups.

If you’re a regular listener of this podcast, then you hear me talk a lot about Jane. She died on April 3rd, 2017 at the young age of 36 from leukemia. What I don’t talk about often is how she inspired the book, The Entrepreneur Ethos, and how she helped my company, Lab Sensor Solutions, get into Batch 14 of 500 Startups. Both of which are relevant to what I have learned from interviewing 100 entrepreneurs for the podcast. Let me explain.

We Have the Same Last Name

Jane’s maiden name is Yin. Thus the Y in her company JSY PR & Marketing. She was a master networker and when she heard me one day talking about 500 Startups, she quickly did some research and found another Yin that worked there. Elizabeth Yin (she’s now at The Hustle Fund) to be exact.

I don’t know how unique the name Yin is but for reasons I still don’t fully understand, Jane contacted Elizabeth and they had coffee. During the conversation, Jane brought up Lab Sensor Solutions and within a couple of weeks, I had my own meeting with Elizabeth at the Mountain View office of 500 Startups.

Let’s pause here for a second because this is the first (of many) actionable insights that I’m going to share with you. This one you won’t hear on any of the 100 episodes I did because it’s from Jane.

Jane’s Insight: Find a connection. Any connection to someone you want to meet and reach out respectfully. Don’t annoy them but add value to the interaction and always follow up.

Long story short, Elizabeth introduced me to Marvin Liao (Episode 6), who at the time was running the San Francisco accelerator program. Over the next 3 days, I talked to Ed, Pete, and Andrea. By the 5th day, we got in! This leads to the next insight.

Jarie’s Insight: Be prepared for when an opportunity comes to you. Practice giving your demo or pitch until it’s second nature. Always be ready to say yes to a meeting.

It’s amazing what happens when you’re prepared to take advantage of an opportunity. Mix in a little luck and that’s what it’s like to be an entrepreneur.

How The Entrepreneur Ethos was Born

Our 500 startups batch, Batch 14 to be exact, had about 30 companies in it. As a team, Lab Sensor Solutions was on the older side. I am pretty sure that our CEO, Geoff, was the oldest batch member at 65. Let’s just say we had a lot of battle scars and grey hair. For whatever reason, we’d get asked a lot of questions about startups from some of the younger teams and first-time founders. After a couple of weeks of this, Jane encouraged me to start interviewing people and that, my friends, is how I started the book and then 3 years later, the podcast. Of course, there was a lot of work involved but that’s the gist of it.

Collection and Organization of the Actionable Insights

When I was looking back at all the show notes from all those interviews, it was daunting to figure out the themes and how to organize them all. Thankfully, in my talent stack is the capability to use Machine Learning. Specifically, topic analysis to figure out the themes for me. Well, not exactly for me since there are several limitations on topic analysis for this kind of thing.

For this type of analysis, you want to reduce what you have to organize into the most relevant text. The text I chose to look at was the Actions to Try or Advice to Take section that each interview has. All told, there were over 500 bullet points from the 100 episodes. I actually now changed the name to Actionable Insights based on listener feedback.

Reduction via Machine Learning Topic Analysis

After I compiled the over 500 Actions to Try or Advice to Take into one file, I ran it through Amazon’s Comprehend Topic analysis tool. This process pulled out 20 topics that each one of the lines fit into. I took the top 2 topics and figured out which lines went to them. That reduced the total down to below 250. Winning!

From there, I went through them all to categorize them down further into the 27 actionable insights below. I won’t go through that process because it’s more subjective than objective but I am proud of the list and I feel it reflects all 100 episodes.

One more thing before we dive in. After each insight, I’ll also give you the episode or episodes I feel does the best job of explaining the insight.

I hope you enjoy it as much as I did compiling it.

Insight #1: A Startups Default is Failure

I first heard this from Marvin Liao’s interview and it has ringed true with everyone I have talked to. It’s not that everyone was negative about the change of failure; it's that a startup is so hard that the odds are against you.

This idea is why the first tenant of The Entrepreneur Ethos is -- Failure is an option but never the results. Yes, you will probably fail but the more you try, the better the chance of success. So always give it your best.

The best episode for this is episode 6 with Marvin Liao on how to Sharpen your Ax.

Insight #2: Take Care of Yourself to Stay Creative

Creativity is an important part of being an entrepreneur. Protecting your well of creativity has a lot to do with taking care of your mind, body, and spirit. All three of those things are intermingled. If you’re working too much or too stressed out, ideas will be hard to come by.

Most guests had a daily routine of either meditation, exercise, or reflection that kept them centered and allowed the creative juices to flow.

Anji in episode 7 as well as Leslie in 4 does a great job of explaining the importance of taking care of yourself to be more creative.

Insight #3: The Answer is Not in the Building

Several of my guests talked about how they had to hit the streets to validate their idea. This theme of getting out in the world and talking to potential customers is an important aspect of being an entrepreneur.

I try to schedule this type of thing so that I do it. For me, my pervertible “not in the building” happens to be the podcast. For you, it might be handling customer service calls or attending a virtual or hopefully soon, live event.

Khiry’s episode 8 takes this to the extreme and his story of how he got his Guinness world record is inspiring.

Insight #4: What You Say Matters More Than You Think

Words matter. As the leader/boss, what you say will ripple through an organization like a stone thrown into a still lake. Don’t use words you don’t want to be repeated. Constantly think about how your words will be heard. The key difference is not what you say but what people hear. Context is important as well. Strive for clarity no matter the situation.

Episode 13 with Kevin and our discussion of the water you swim in as it relates to culture is a good example of this.

Insight #5: Configure Rather Than Customize

Think of your product or service as something configurable as opposed to doing one-off customizations for customers. This is especially important for B2B companies that usually land big corporate customers that will treat you like an extended development team and suck all your resources to customize your offering for them.

Gregory’s episode 25 is a wonderful one to listen to as he talks about how he scaled his real estate management software company.

Insight #6: Cultivate a Vision of Where You’re Going

It’s important for so many reasons to have a clear, concise, and compelling vision of where you want your company to go. As a founder or CEO of a company, this is the single biggest value you can contribute. Without a clear, concise, and compelling vision, you’ll waste time, effort, and money.

Spend more time and effort than you think you should on this. I’d say it should be a daily mediation or at least a weekly reflection. The other piece of advice would be to communicate more often than you think.

Episode 18 with Amy on the Perfect Fit as well as episode 29 with Jennifer on Cultivating a Vision will be good places to start.

Insight #7: The Best Story Wins

We all think that our awesome technology will win the day and usually, it does not. Of course, you’ll need the tech to work but what my guests have regularly told me is that it’s the story about your vision and company that makes a difference. No amount of technology can compensate for a badly written story.

Tom’s episode 26, Tim’s episode 69, and Chris’s episode 50 are master classes in the power of story. In particular, Tom’s idea of making them care is what every single brand should strive for.

Insight #8: Take Luck Over Skill

The amount luck has played in the success of those I have interviewed seems like it’s made up. The truth is, most of those I have interviewed have a healthy respect for luck and would take being lucky over having the skill pretty much 10 to 1. I’m in the camp as well because it’s luck that allows you to use the skills you have. Without luck, no amount of skill matters.

So how do you make luck? That’s easier than you might think. Luck is about the opportunity so if you create more opportunity, then you’ll create more luck.

Ben’s episode 24 about learning every day is one to check out on this.

Insight #9: Have an Abundance Mindset

Instead of a scarcity mindset, which is the belief that there is a finite amount to go around, adopt a mindset of abundance where there is an infinite amount of opportunity. This seems to be another universal I have observed with guests. They have an attitude that they want to create more instead of dividing up what’s already there.

The opposite of abundance is scarcity and when driven by the scarcity mindset, it’s always about getting yours as opposed to expanding the pie.

I’d say the best episode for this would be Joanna’s episode 23 about not afraid to fail. Her attitude about sharing her knowledge by writing books is spot on about the abundance mindset.

Insight #10: Love the Journey Not The Rewards

Startups take forever to become successful. All of those “overnight” successes took way more overnights than most will admit. Enjoy the ride and don’t worry too much about the trappings of success. It’s fleeting and may not come.

Several of the entrepreneurs I interviewed had their successes come from a “failure” that taught them the right product to build. A lot of that timing was also due to luck as well.

Richard’s episode 22 is a good example of this as well as Anupam’s episode 21.

Insight #11: Steal Good Ideas

Look for good ideas to steal in other places that apply to your market. These ideas can be found in any market and be applied to any other market. This is especially true for industries that are technology laggards like healthcare and governments. Several of the entrepreneurs I interviewed took their knowledge in one area, SaaS, and applied it to healthcare.

What I mean by stealing is not someone’s actual product or service but the concept or idea. This whole steal like an artist can be controversial but if you have an abundance mindset, you’ll soon realize that ideas are worthless without execution.

Episode 34 with Nadine,  episode 37 with Ryo, and episode 38 with Mark talk about the creative process and more importantly how a good idea can be made your own.

Insight #12: Finding a Cofounder is Like Finding a Spouse

A lot of my guests talked about the challenges and struggles they had with co-founders. The best advice they gave was to take it as seriously as finding a spouse. What that means is that they looked for the intangibles that make being with them uplifting and pleasant as opposed to say technical prowess. This was important for finding a tech co-founder since that tends to be hard for some non-tech co-founders to evaluate. Some of my guests have a spouse as a cofounder.

John’s episode 35 has a good discussion about this. If you want to hear about what it’s like to found a company with your spouse, then check out episode 21 with Anupam and episode 32 with Dilip.

Insight #13: Future Sales Come From “Existing” Customers

Sales always seem to be a sore spot for entrepreneurs. I’d say almost everyone I interviewed had some sort of heartburn over sales. I’m included in this group because I’m not the biggest fan of selling but over time, I have learned to embrace it.

You’ll notice that existing is in quotes. The reason being that your current customers will be the best source of new customers. I heard a lot of this from entrepreneurs who were starting to get product market fit along the road to full go to market.

One of the best discussions about this idea was in episode 54 with Jerry when we talk about Don’t sell. Solve problems.

Insight #14: Keep It Sesame Street Simple

Startups are complex and only get more complex as time goes on. Almost everyone I interviewed was always trying to simplify, simplify, and simplify some more. This is easier said than done, especially if it’s a technical offering.

What seems to be a theme on this is that the curse of knowledge is more of a curse of assumptions that can derail even the most diligent entrepreneur. I think this is best summed up by if you can’t explain it to your grandmother then it’s too complex.

This concept is also about telling a good story as well. We talked about this in insight #7 and this idea of keeping it simple applies to that as well.

Manu’s episode 47 on Do one thing well is a great example of this.

Insight #15: Be of Service

Service was a big component of all my interviews. Service to one’s employees, market, and fellow entrepreneurs. This seems to be ingrained in the job since it’s such a hard thing to be successful at. This difficulty naturally leads to asking for and offering up help.

I always like to say that this job is so hard that you can (and should) scream from the top of the mountain what you’re doing and who might be able to help.

Episode 45 with Roy is a great example of being of service and trying to find the best way to help.

Insight #16: Stay Aligned with Your Why

Your ‘why’ is the internal reason you do what you do. This transcends all external motivations like fame, fortune, and prestige. Lots of my guests had a strong internal ‘why’ as to their purpose for creating their company or for what they do.

As fame, fortune, and prestige came to them, it got harder and harder to stay aligned. Almost all those external things focused them away from their ‘why’ and they regretted it. So the insight to keep here is don’t forget why you started the company in the first place.

Episode 56 with Ash, episode 53 with Phil P, and episode 66 with Lee are all good places to start.

Insight #17: Curiosity is an Antidote to Fear

Entrepreneurs are naturally curious and this seems to counteract fear. Specifically, fear of the unknown. As I always like to say, if you want to be an entrepreneur, you need to be comfortable being uncomfortable. This comfort level is derived from having a curious mind that can handle the zigs and zags of business and life.

Being curious also allows you to remove yourself from the emotion of a problem and focus on the problem.

A great episode to listen to about this is episode 78 with Nir.

Insight #18: SALE(s) is NOT a 4-letter Word

Sales is a numbers game. Don’t take it personally and no matter how much you “hate” it, learn to do it. Your job as an entrepreneur is to sell your ideas to folks who are happy with the status quo. Don’t get me wrong -- this is much easier said than done.

As the founder or CEO of a startup, you’re the first salesperson. If you can’t sell to customers, then no one can. Again, learning this is hard to do and I have a ton of respect for anyone who can sell anything. It’s a hard job and supercritical to a company's success. I’d say it’s more important than any feature or function a product has.

Just so you know, I’m really bad at sales. It makes me squirm and I feel so bad when I have to do it but do it I must.

Stan’s thoughts on sales in episode 62 are practical and also make it more accessible. Jan’s thoughts in episode 75 are also great.

Insight #19: Don’t Give Up

The majority of the folks I interviewed had a story or two about how they kept at it a little longer and bingo, the company turned around. It’s been my experience that most new founders quit too early or underestimate how long development or the sales cycle will take.

While there are no hard and fast rules on when to give up, I’d say that pushing a little harder when you think you should quit is advisable. As one of my old bosses used to say, never let money get in the way of progress or the other one was I never gave up too soon.

There are so many great episodes about not giving up but the one that sticks out to me is episode 60 with Michelle. Michelle has been traveling all around the country in an RV that captures all sorts of stories about entrepreneurs and how they are coping with COVID 19.

Insight #20: No One Has All the Answers

A universal truth is that you’ll never be 100% sure of anything when it comes to your business. The challenge is to make educated guesses that move the company forward. Waiting for perfect information will always fail since there is always another competitor that takes a risk on imperfect information.

The trick, it seems, is to make your best guess given the information at hand and be flexible to change your mind.

Episode 61 with Jaryd and episode 65 with Nicole give some great insights into just doing it.

Insight #21: Take Your Time But Hurry Up

Startups are all about speed. This speed is the primary reason they crush big companies. It comes at the expense of risk and sometimes “speed” kills. A lot of my guests had a sense of urgency but not a sense of panic. This meant that they pushed forward at a pace that maximized progress while attempting to minimize bugs. This is a delicate balancing act that has bitten some guests to the point that they had to shut their company down.

Episode 77 with Sam and how it’s important to start somewhere is insightful on this.

Insight #22: There’s Always Value in Honesty

The truth will set you free as the saying goes and it seems that most of my guests feel the same way. The complexity of creating something from nothing is hard enough that being honest will get stuff done quicker. I think this is one of the best aspects of being at a startup. Honest feedback along with telling the truth is one of the hallmarks of a great entrepreneur as well as a great company.

Those who try and hide the truth will always be at a disadvantage. Nir in episode 78 is the one that coined this term and I feel that it’s an important part of leading the entrepreneur lifestyle.

Insight #23: Everyone Has a Part to Play

The challenge with scaling a company is that, as the team grows, there will be all sorts of different skill sets and personalities in play. For hard-charging type A’s, this can be frustrating. This is especially true when you as a founder have to assess someone's capabilities that are outside your area of expertise.

What most of my guests have found is that they need to keep an open mind and find the best people they can. This can be hard with hard to quantify things like PR and marketing where the metrics and impact are harder to nail down.

Cody in episode 80 has a great story about this. John in episode 79 takes this idea to a different level when we talk about who advocates for entrepreneurs.

Insight #24: Clarity Over Everything Else (including Product)

We touched on keeping things simple above and this one takes that to the next level. Clarity of message and thought is the most important idea to cultivate within an organization. To put it a different way, you want your ideas to be Memes -- easily reproducible for maximum spread.

Clear, concise, and compelling messages are what Peep talks about in episode 81, and his company Wynter helps folks do that. I’m a big, big fan of Wynter and am also one of their testers.

Insight #25: Always Be Cultivating Relationships

Networking is another one of those activities that many entrepreneurs stop once they start working on their company, which is a shame. Organizations are built on relationships and you never know when or with whom your next opportunity will come. Image if Jane never reached out to Elizabeth. Chances are, you’d not be listening (or reading) this right now.

The most unlikely episode that explores this is from the lead singer of Prison, Johnny in episode 84. Katie (episode 82) and James (episode 85) also talk about this.

Insight #26: Start Promoting Earlier Than You’re Comfortable With

Promotion takes time. Lots and lots of time. A general heuristic that seems consistent among all my guests is that it takes as long and as much money to promote and market a product as it took to build it.

While I’m sure some great offerings have done it faster, this seems to jive with what I have seen in the press as well. What this means is that you should consider and do whatever you can to promote your company as soon as you can.

Episode 91 with Tracy is a good one to understand the power of PR as well as episode 94 with Farzad.

Insight #27: You Can Never Ship Too Soon

Perfect is the enemy of good enough. This seems to be the hallmark of the “move fast and break things” startup culture. While I’m sure there are times where this is true, most of the time, shipping something is much better than shipping nothing.

This attitude I think also gives you and your team the discipline to figure out what matters. In the end, a shipped imperfect product will trump a perfect product that’s delayed every single time.

Episode 90 with Roger talks about this when he discusses how he pitched a client and when they said yes, he had to create his company. Farzad also talks about this in episode 94 as well when we discuss beta testing. A lot of my guests do beta testing to understand how their product will perform when customers use it.

Thanks to All My Guests and Listeners

Whew! That was a lot to get through. Thanks for spending the time with me today. I hope some of these 27 actionable insights you can take action on today.

Special thanks to Shaun, Angel, Sydney, Jacob, Nick, Sarah Beth, Farzad, Dallen, Swire, Tracy, Roger, Ugi, Bharat, Sedale, Kuda, James, Johnny, Phil, Katie, Peep, Cody, John, Nir, Sam, Dan, Jan, Trav, Dylan, Christina, Dustin, Eric, Tim, Nelly, Brenden, Lee, Nicole, Robert, Priya, Stan, Jaryd, Michelle, Ozzy, Aman, Belle, Ash, Doug, Jerry, Phil, Phillip, Donteacia, Chris, Nate, Janet, Manu, Neville, Roy, Shana, Claudius, Adam, David, Denise, J, Mark, Ryo, Melinda, John, Nadine, Jeremiah, Dilip, Brady, Jo Lynn, Jennifer, Kurt, Tom, Tom, Gregory, Ben, Joanna, Richard, Anupam, Nathan, Amandeep, Amy, Mark, Marvin, Jerod, Greg, Kevin, Nathan, Marc, DJ, Candice, Khiry, Anji, Marvin, Mark, Leslie, Ravi, and finally my first interview Grant.

It was an honor to have you on the show.

Before I end, I’d like to say thanks once again to Alyssa Colton who does all my show notes. Without her help and awesome eye for detail, I could never have compiled the above list.

So thanks again, Alyssa.