Home For Dinner: Recent Episodes

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Entrepreneurship is kind of like social media.  Usually we only see (and share) the highlight reel.  We don’t get to peak behind the scenes of what people’s lives are really like.  Granted – if you’re a single twenty-something year old grinding it out 80 hours a week, it’s almost glamorous to be living off ramen noodles to build the next big thing because you can say “remember when???”

But for those of us with families, it can seem daunting to make the jump. And then once we do, the commitment is almost always more than we expected.

That’s what’s special about our next guest.  He’s at a point in his career where he serves as an advisor to entrepreneurs and works in venture capital.  And, at least for me, that’s a place I would like to get to, because if you’re involved with venture capital, it’s generally an indicator that you’ve had some modicum of success yourself.

But what we don’t often see is the other side, and what it took to get there.  I don’t mean about the business struggles…those are documented well enough.  I mean the side that isn’t talked about, because frankly, I don’t think many entrepreneurs have been able to successfully navigate it.  

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A successful tech startup and exit; teaching at Indiana University’s prestigious Kelley School of Business; formerly the Chief Marketing Officer at Indianapolis-based startup Powderkeg; and founder and CEO of Dreamfuel.

At first glance, Kevin Bailey is unassuming.  He’s got an easy-going, laid back conversational tone, and when you sit down to talk to him, you realize he’s sincerely interested in you as a person, despite an impressive pedigree. 

But what you don’t see are the scars and hard-fought lessons learned that have impacted Kevin’s outlook on entrepreneurship and life today.

Being acquired is a dream that many tech entrepreneurs work towards.  It’s what’s known as having a successful “exit,” and, rightfully so, it’s a badge of pride for the co-founders who have successfully navigated an acquisition. 

So who would’ve thought that as a 27 year old co-founder looking at multiple offers for his company, Kevin was about to enter one of the most difficult periods in his life?

Kevin shares in raw detail the reality of what happens when you lay it all on the line for your company, working as though burn-out can’t happen to you.  And it’s not the ending you’re expecting - this isn’t a Cinderella story ending that you read about in magazines like Fortune and Inc, or the many business podcasts out there.  This is a story about the highs and lows of running a high-growth company, the lasting effects of making decisions with a scarcity mindset, and what the future looks like when you’re burned out, disillusioned, and are holding on to just a glimmer of hope.

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Quiet confidence. That’s what comes to mind when I think of Mary.  The kind of person who can inspire you to conquer the world with just a few words, or can tell you that your idea is legitimately terrible, and you walk away respecting her even more.

She can command the room if she needs to, but is also satisfied to help others forge ahead by blowing wind into their sails.  That’s Mary.

We met at the LaunchIt course put on by Nucleus here in Louisville, where she was serving as the director of the program.  Throughout our time together, I regularly approached her about the tensions we talk about on this podcast.  Questions like:  how smart is it to pursue a business opportunity when you’ve got a wife, four small kids, and a mortgage?  How do I know when to shut down that venture, and do something more traditional for a while?

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Roy Englebrecht and I met in a freshman level class in college.  Of course, I should probably clarify something - I was the student, and he was the guest lecturer.  I remember sitting in class and hearing my professor announce that a real-life entrepreneur was going to come to and share his real life experience starting and growing a company.  I really wasn’t sure what to expect - this whole “entrepreneurship” thing was pretty new to me.

The year was 2010, the iPhone was still relatively new, Facebook had recently upset MySpace as the most popular social media platform, and entrepreneurship as a “thing” was just starting to become vogue. 

But Roy did more than just share about how he saw his first opportunity, and worked hard to turn it into what is now.  He inspired me to do that same - and that’s when the whole world of entrepreneurship opened up in front of me.  The good, the bad, and the ugly.

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That’s what it sounds like when I come home at the end of a work day. My family is there, not only waiting for me, but excited to see me, reminding me about what’s important in life.

Because when you’re an entrepreneur, when you go into business for yourself, those types of things...your family eating pizza on a Friday night, your friends grabbing lunch at your favorite spot, your spouse offering a careful listening ear...those unquantifiable things are quickly pushed to the side when you’re working to create something from nothing.

Inc. Magazine is a business magazine dedicated to small business owners. They cover everything from tech and marketing, to human resources and fundraising. It’s practical, and inspiring. And also a little scary. Because while there are all of these great stories of entrepreneurs getting funding, creating amazing products, and sometimes literally changing the world, there’s always a question that’s sitting in the back of my mind.

Really, it’s not so much a question as it is a latent fear…sort of like the feeling you get when a lump forms in your throat, but instead of sadness and tears, it’s a visceral reaction to one of my biggest insecurities.

And this question, this fear, only gets worse when you realize that answering the question honestly might also mean giving up something you’re really passionate about.

Steve Jobs. Richard Branson. Elon Musk. Those guys really have changed how we do things everyday.

Steve Jobs created something we didn’t know we needed with the iPhone.

Richard Branson has disrupted multiple industries and inspired an entire generation to jump into entrepreneurship.

And Elon Musk has literally reached for the moon, and shot straight past it.

They seem happy, fulfilled, and generally say the same when they're asked. People listen intently as they share their morning routines, what they look for in leaders, and how they evaluate opportunities.

These entrepreneurs, and others like them, have reached the pinnacle of achievement.

They’ve climbed a level of success that most can only dream of.

But maybe that’s the catch.

For all of those achievements, there’s one thing that’s always missing…

Because it seems like reaching that level of success requires letting go of something that’s valuable, something that songs are written about, and lives are committed to keeping.

And the thing that’s missing is their families. Or lack thereof.

My name is Philip Devine, and my biggest fear is losing my family on my entrepreneurial journey. The sounds you heard at the beginning, with my kids running up to me, and my wife giving me a kiss when I come? I don’t want to give those up in order to become a successful entrepreneur…or that version of a successful entrepreneur.

And who knows, maybe I don’t have to. Maybe that’s a false dichotomy I’ve dreamed up. But if you’ve paid any attention to startup culture or Silicon Valley, the message is pretty clear: when you start a company, especially a high-growth company with outside funding, you put it all on the line…your family be damned.

So that’s the question: can you be a successful entrepreneur, and still have a healthy, growing family life?

Welcome to Home for Dinner, a series focused on exploring that very question.

Maybe you can have it all. Or maybe not

Everybody loves a hero. And, on some level, it’s because we aspire to be that hero. My 4 year old son is all about playing Batman and saving the day. If I’m honest, I wouldn’t mind being Thor for a day or two!

But if you take a step back, you realize that the things that made the hero “heroic,” the trials they had to go through, are usually pretty rough.

Look no further than the brave men and women who serve our country...often times the ones with the most medals have also experienced the most horrific things, sometimes giving their life in the process.

Everybody loves a hero. But I would venture a guess that it’s not always all that it’s cracked up to be.

Entrepreneurship and business also have their heroes. The Jack Welches, Steve Jobs, Mark Zuckerbergs, Jeff Bezos, and others write books, command massive audiences (and dollars), and inspire entrepreneurs.

But these heroes sacrificed the one thing I, and I’m guessing you, aren’t willing to: our families.

We’ll spend the next couple episodes not just learning how other entrepreneurs have successfully navigated family and work, but also understanding when they were able to say “no.”

We’ll uncover a quiet, but successful group of entrepreneurs. And hopefully, you’ll find a hero as well.

This is so much bigger than work-life balance. This is so much more than the next productivity hack. This is about helping you build a successful company, and make it home for dinner.