About this episode

In this episode, we’re reflecting on the key entrepreneurial learnings across our 100 founder interviews. To be honest, when I first started The Startup Story, I had no intention of it becoming a full-time venture. I simply wanted to fill a personal void created by a previous employer. However, it is now two years and 100 episodes later and I am all in.

Soon after I decided to be intentional about making The Startup Story my full-time endeavor, COVID hit. When this happened, everything got flipped on its head. I’ve had to lean into the learnings from the entrepreneurs I’ve interviewed over the past two years. I know these learnings have impacted all of you, as well. Tune into this episode to hear and reflect on these key truths that have sustained many of us through 2020.

In this episode, you'll hear.

  • How The Startup Story came to be.
  • How failure drove me to seek to understand what successful entrepreneurs were doing.
  • The worst thing you can do in the midst of challenge or disruption.
  • The upside of COVID for business owners.
  • Why entrepreneurship is supposed to be hard and how remembering that truth helped me thrive during COVID.
  • How entrepreneurship more resembles a journey than a title or role.
  • Why even hard chapters in our lives aren’t wasted.

Resources from this episode

Join Grindology: https://grindology.com/
ExpressVPN: Get 3 Months Free → ExpressVPN.com/StartupStory
Get Emails: https://app.getemails.com/referrals/newaccount?ref=R18HWW5
The Startup Story Inner Circle: https://www.thestartupstory.co/vip
The Startup Story on LinkedIn: https://www.linkedin.com/company/thestartupstory
The Startup Story is now on YouTube: https://www.youtube.com/jamesmckinney
The Startup Story on Instagram: https://www.instagram.com/thestartupstory

Share the podcast

The Startup Story community has been so incredible sharing our podcast with others, and we thank you! We do have more stories to tell and more people to reach. There are three ways you can help.

First, the most powerful way you can support this podcast is by leaving a review on Apple Podcasts or wherever you listen to podcasts.

Second, follow us on Facebook and Instagram, and be sure to share your favorite Startup Story episodes with your friends and on social media. Tag or mention @thestartupstory.co so we can give you a virtual high five and a thank you!

Lastly, share the podcast on LinkedIn. The Startup Story podcast is for entrepreneurs. Don’t underestimate the power of sharing on LinkedIn so other entrepreneurs can discover us.

With your support, we hope to further our reach in encouraging and inspiring the founders of today and tomorrow. Thank you!


If you like this podcast and are thinking of creating your own, consider talking to my producer, Danny Ozment.

He helps thought leaders, influencers, executives, HR professionals, recruiters, lawyers, realtors, bloggers, and authors create, launch, and produce podcasts that grow their business and impact the world.

Contact him today at https://emeraldcitypro.com/startupstory

Episode transcript

Hello everyone. I'm James McKinney, creator and host of The Startup Story, and this is our 100th episode.

Every wildfire began with a spark. Every superhero has an origin story. And every single startup has a moment that they point to as their beginning. And every founder has a purpose that drove them in the midst of all obstacles. THAT is The Startup Story.


James McKinney: Welcome to a special episode of The Startup Story podcast as we reflect on some key entrepreneurial learnings across our 100 founder interviews. You know, it's a bit surreal to say that out loud because two years ago around this time I had just fully committed to creating a podcast. Now here we are, two years from finally deciding I was going to start this journey, to celebrating our 100th episode. You know when I launched The Startup Story podcast I had absolutely zero intention on it becoming my fulltime venture. I mean to be fully honest, I only started The Startup Story to fill a personal void created by a previous employer that I had.

See in 2017 and now that I think about it, I don't think I've ever told this story before in any episode, so this is the first time you're hearing how The Startup Story kind of came to be. But in 2017 I joined a software development company to oversee their sales efforts. This was actually the same software development company that built my mobile app called Simple Deal. My experience of trying to build a business around a mobile app is a whole other podcast episode so we're not going to get into it here, but just know that I could never gain any traction with the app so I shut it down at the end of 2018. And during this whole time while I was working with the software development firm and trying to build out my app business, I started networking with other entrepreneurs. My intent in doing so was actually two fold. First, to surround myself with people just like me and second, to generate some leads for those needing technical assistance.

Now, I don't know if you knew this or not but not all technical founders are actually technical. So being that my 9 to 5 job was to sell custom software development, I thought being around a demographic that might need technical assistance would be a great lead source. Well one of my mainstays when it came to the entrepreneurial community was the organization called Startup Grind. Startup Grind has hundreds if not a few thousand I guess chapters across the globe that meet at varying intervals and under varying formats. The premise is to bring entrepreneurs together to help each other. I loved it so much that I ended up starting a chapter in the Santa Clarita Valley, which is just north of Los Angeles for those that are unaware of the area. And again, my intent with starting that chapter was twofold. Again, to surround myself with people who thought like me and were driven like me, and two to help position the software development firm that I was selling for as the place to go to for technical development in the area.

Well, our first Startup Grind event was incredible. We hosted Matthew Arevalo, cofounder of Loot Crate, and over 100 entrepreneurs gathered to hear how Matthew helped to grow Loot Crate to $100 million in just three years. The energy was electric and the community of entrepreneurs was remarkable. That event really helped to build momentum for the chapter and our brand. Well, each month we would host an event with a featured founder and each month we would have a turnout of at least 80 plus entrepreneurs, and then it all had to come to an end. Now remember, one of the reasons for hosting these events was to generate leads for the software development firm.

Well after six meetings and zero dollars in revenue generated the president thought it wasn't working so we needed to stop our involvement with Startup Grind. Now obviously, I disagreed but I wasn't the decision maker. I was an employee at the time. And I saw these events much like I see many things in my life as a long-term play. I'm a relational person at my core and for me I saw these events being something that I would take eight to ten months before we would actually see a project come out of it, especially since I was trying to sell customer software development that costs around $100,000 or more. I wasn't trying to sell a $5,000 website. Now just for all of you listeners that are sales oriented people out there, 12 months after our very first event I closed two projects totaling about $600,000 in revenue from relationships developed during my time leading Startup Grind. Like I said, I believe in the long game. I'm not a fan of short-term thinking.

At any rate, to make a long story short I had to stop leading the Startup Grind chapter and it was actually our very last event where the seeds of The Startup Story began to stir. In my last event there were three different people, all of which did not know each other, came up to me and asked me if I had a podcast because they would listen to it. See, at these events I would interview founders just like I do for The Startup Story, and it was those conversations that people resonated with and kept coming back for. Yet, I had zero idea what it took to execute a podcast. I was great at connecting with successful founders and unpacking their journey in a way that delivered real value to those in attendance. [05:00] I was incredibly passionate about that, but I had zero idea about what was entailed to launch a podcast. So the idea of a podcast just sat as an idea for a few months.

Then I realized that I had this deep seeded internal need to keep connecting with successful entrepreneurs to understand their journey, especially because I had just decided to shut down my fourth attempt at a startup. After failing that fourth time, I had a hard time believing that my failures were about my personal abilities and not simply a gap in understanding and execution. I had to understand why some entrepreneurs were succeeding and why I wasn't and I realized that other people were probably just like me. It was there that The Startup Story was birthed, and on January 15th of 2019 we released our first three episodes and it has been a wild ride ever since. But like I said earlier, I never had a vision for this being anything but a side project that met a personal need I had to meet successful founders and to understand their entrepreneurial journey and why they were winning.

It wasn't until six months after our launch that a UK listener messaged me on The Startup Story Instagram page to let me know the show was, I think at the time somewhere around like the top 25 in the entrepreneur category. And that message blew my mind because I wasn't tracking any metrics other than downloads. Again, I did not create The Startup Story for any reason other than to share the learnings that I was desiring to learn for myself from massively successful people. Well, that success metric gave me a reason to start thinking about what The Startup Story could become if I was actually intentional about it. So in October of last year I went all in on The Startup Story and it became my fulltime endeavor. We jumped into 2020 with excitement and ambition, like I'm sure all of you did. In fact, we had been planning a large scale in person event at the global headquarters of the Dallas Cowboys. We were bringing in three exceptional founders to speak to us as well as inviting 1,500 entrepreneurs to attend. It was really going to be a big deal. I mean we were about to sign a six figure deal for a title sponsor contract for two live events that were supposed to take place this year. Well, that was until COVID hit and changed everything for everyone.

Well within 30 days we lost all in show advertisers and of course live event sponsors. I know that narrative is not unique to me, but as I know you can relate it sure did feel like a personal struggle. Since April of this year I've had to lean in on all the tremendous learnings that I've been fortunate enough to obtain from my 100 founder interviews. I know those learnings have also impacted you as well because I hear from many of you about a key learning or perspective shift that has taken place because of a founder interview that you heard. So as we celebrate this incredible 100 episode milestone, I thought I would share with you the key truths that I have relied on throughout 2020.

That first truth that I've relied on is that the worst possible thing you can do in the midst of challenge or disruption is to stand still. In fact, our very first episode with Jason McCann, founder of Varidesk now rebranded as Vari, shared his mantra if you will to keep rowing until the wind catches his sail. The truth of the matter is that quitting is the only way we lose. As the world was falling apart this past year, I never stopped believing that The Startup Story was a platform that entrepreneurs everywhere needed. I just needed to figure out ways to generate revenue to weather this COVID storm. From April to today my audience has tripled. Why would I call it quits just because I cannot see a path to revenue given the temporary state we all found ourselves in? and again, I know I was not the only one in this place but it sure felt isolated and personal. And that's why you've heard me say time and time again that I believe any brand that is able to scratch and claw their way out of 2020 and into 2021 is going to be set up for a tremendous opportunity. If your business is still alive, even if it's on life support, think about all the lessons you've learned about your business that only something crazy like COVID could have revealed. As hard as it may be to acknowledge, COVID did have an upside. It revealed a vulnerability in our businesses that we would never have seen otherwise.

Jason McCann's story is not the only one that reveals this truth. Jamie Schmidt talks about this truth as she built Schmidt's Naturals to a point where she sold it for over $100 million to Unilever. Kelsey Carroll speaks to this truth in last week's episode as she talks about losing her live event business and pivoting to create Stand Up Stations. As long as we keep moving forward then we will make progress. We just have to make sure that we're always making some amount of progress.

Before we continue on with our 100 episode celebration I want to remind you about our Grindology Subscription Service and our $12,000 giveaway. Like I mentioned, even in a crazy year like 2020 you have to keep making progress. Well, for us progress meant that we had to keep delivering you the fuel needed to help in your entrepreneurial journey. [10:00] And that is why we launched Grindology.com. as a Grindology member you will receive a custom curated entrepreneurial resource kit every single quarter. Within every Grindology box you will receive two 12 oz. bags of our uniquely roasted coffees specifically crafted to help fuel your hustle as well as a limited edition mug and the current issue of Grindology Magazine that is chock full of tactics and strategies provided directly by founders and brands that have proven those tactics to produce results. This is not a magazine full of journalistic content. It's a tactical manual for entrepreneurs by entrepreneurs.

To celebrate our launch we joined forces with Design Pickle to award an entire year of their pro service plan that provides unlimited graphic design and creative services to one lucky winner. This prize is valued at approximately $12,000 and one lucky Grindology member will win it if they find the golden pickle within our premier shipment this January. You can learn more about this promotion and how to enter at Grindology.com/goldenpickle. Our Q1 box is our first shipment and it will be an exclusive offering so secure your box today at Grindology.com. Now let's get back to our 100th episode celebration.

The second truth that I clung to throughout this year is that entrepreneurship is supposed to be hard. There are so many easier ways to make a living. We choose this. We opted to forgo a stable 9 to 5 job that provides a paycheck and health insurance to try and create something ourselves. we willingly stepped onto this path knowing it was not the easiest option out there. In fact, if we're really honest it is the unknown challenges that drew us to this journey. Everyone has a book full of dreams and ideas, but only the few are willing to put it out there to try and execute on one of those ideas. If it was easy it wouldn't be rewarding. I'm reminded of that scene with Jack Nicholson in the movie A Few Good Men where he just unloads on Tom Cruise's character. In fact, it's probably one of the most popular monologues in cinematic history. You know the scene. In that scene he states, "You don't want the truth because deep down in places you don't talk about at parties you want me on that wall. You need me on that wall. We use words like honor, code, loyalty. We use these words as a backbone of a life spent defending something, you use them as a punchline." Man, I can go on and on. That quote, that monologue, that scene with Jack Nicholson is so good. But that same passion and drive that he speaks to in that segment, it's a bit true for the entrepreneurial journey as well.

Despite how hard it is, we need to pursue this idea and concept. We can't imagine not dealing with the challenges we face. With that truth in mind, there is no good that comes from wallowing in our frustration and disappointment. COVID didn't just happen to me or you. It happened to the entire planet, so yes while we might not have signed up to navigate a business in the midst of a pandemic, we did sign up knowing that there were unforeseen forces that we had to solve for and provide a solution around. Larry Namer, the founder of E! Entertainment Television, speaks to this when he talks about needing $60 million to start a television network, but only receiving $2 million. Did he just throw his hands up and say, "I'm out, I didn't get what I needed"? No, he took that $2 million, scratched and clawed his way to building a network that would eventually sell for $3 billion. His journey has trial after trial because that is what he signed up for when he left his high-rise executive office to start his own business.

The same truth is echoed from my conversation with Christina Stembel, founder of Farm Girl Flowers. She continues to grow her business regardless of the obstacles thrown at her and venture capital still won't invest in her business because the team doesn't quite, I'm having air quotes here, "the investable look." She didn't sign up to build a business to deal with discrimination within the investment community, but she also didn't stop building her business because of it. No, she solved around it and continues to move forward. Like I said, reminding myself that entrepreneurship is supposed to be hard helped me quite a bit this year because it reminded me that this journey is about solving problems, period.

Lastly the third truth that I grasped onto is that entrepreneurship actually more closely resembles a journey than it does a title or role. See every single founder that I've interviewed has reached the success that they have because of many previous chapters in their life. Throughout our 100 episodes you've heard me refer to the breadcrumbs of life, and if you're a person who likes hiking or anything outdoors then you probably actually pictured dropping breadcrumbs along a path. But if you're a designer or a developer then you might picture the navigation type of breadcrumb. Either way, they show us how we got to where we are right now. Sure, the analogy also lends itself to the interpretation of the fact that they also show us how to get back to where we were, [15:00] but that's not my point of reference because I'm always about what's ahead and the breadcrumbs of life show us that every single chapter, whether it's a successful one or one of hardship and failure, every single one contributes to where we are today. We learn from every single chapter and we take that learning into our next chapter. There truly is nothing wasted along the entrepreneurial journey, and this is even true for 2020.

I'm excited about what the next 100 episodes of The Startup Story have for us because I'm part of this journey with you. I'm not a journalist who is simply taking notes with my founder guests to write a great article. No, I'm ingesting the learnings just like you are so that my current chapter might be a bit more successful than my previous ones. And I thank you. I am so appreciative of you for being part of The Startup Story community and for subscribing to the show wherever it is that you listen to podcasts. I do not ever take for granted the hours and hours you've invested into the show, and I am forever grateful to you for that.

With that in mind, there are still so many people that are unaware of The Startup Story. I'm talking about millions and millions of entrepreneurs who need to hear these remarkable stories to help their entrepreneurial journey. The Startup Story exists to provide insight, guidance, and inspiration to help entrepreneurs everywhere to either one, begin their entrepreneurial journey with a real perspective of what it takes, or two to give them the quick hit of perspective and inspiration to keep going. Either way, I hope you will consider sharing The Startup Story with your immediate network. You never know who needs to hear these stories. And I say it in every episode because I believe it with my very being, entrepreneurs support other entrepreneurs and I am so very thankful of your support of my entrepreneurial journey.

If you like this podcast and are thinking of creating your own, consider talking to my producer Danny Ozment. He helps thought leaders, influencers, executives, and authors create, launch, and produce podcasts that grow their business and make a real impact in this world. You can contact him today at emeraldcitypro.com/startupstory.

Listen Now

November 24 2020
James McKinney, Episode 100

More Startup Stories

All Startup Stories