Men's Lifestyle

Insights From Bulleit Bourbon Founder Tom Bulleit – Part 1 – Fear Versus Doubt

Tom Bulleit always felt the urge to go against the grain. It took many years, a lot of guts and an equal number of mistakes made, but Bulleit Bourbon is now one of the most popular bourbons in the world.

We sat down for an exclusive interview with the founder of Bulleit Bourbon and Tom didn’t disappoint.

With the timbre of a man pleased with himself and his accomplishments, yet lacking even a shred of arrogance or inauthenticity, he conveyed insight into what it takes to be a successful entrepreneur, the considerations that must be made and taken into account when striking out on your own, and the difference between fear and doubt; how you can harness them but never evade both forever. This is part one in a three-part series.

Male Standard – Walk me through your decision to start Bulleit Bourbon. I read that you went all in. You had this steady job as an attorney and you decided “I want to go into this business.” What was that decision like? Where you married at the time? Did you have to break it to someone else? When did you decide, “I am going to start this business” and go all in?

Tom Bulleit – Well, I was all in emotionally. It was not all in work wise. I had literally started in 1987 and had practiced law for quite a while at that point. And went back to my father and said, “I really want to do this.” I got his blessing at that point, and I was married at the time. With a daughter, Hollis – in 1987 she would’ve been about 14. So, it was obviously a serious economic decision. Literally between ’87 and ’97 I did this business and practiced law – I did both at the same time. As a matter of fact, my banker said to me, “Tom, do not give up your day job for your night one; the end.”

I think that as starting businesses, or as it’s called now entrepreneurship, my first recommendation is always marry somebody with a good job. Or have a partner, somebody with a good job. Because you’re going to need to supplement your income somewhere. Our daughter was in public school but not far from college. So you have all those added concerns. You’ve got a mortgage, once child getting ready to go to college, we were thinking about our second child at that point – Tucker Bulleit, who was born in 1994 – so during those years I made additional commitments. And they were years when – my wife is a stockbroker and a finance person which is a good job but also she was an expert in finance – so I was drilled regularly about how this is going to work and when it’s going to work. “Where are we going with this?” So there were a lot of years where you get one no after another.

I remember through these years I always thought the international market would be as good as the domestic market. And just two years ago we started doing international launches, 26 years into it! That was a big part of what I wanted to do. And on the front end we worked diligently to try to garner international interest, to find some international distributors, things like that. None of which came to anything. It was sort of like one disappointment after another, but learning a little bit each time.

Every time you get knocked down and get back up, you’re going to learn what knocked you down that time! There’s always going to be something else to knock you down, but at least you hope you won’t revisit that situation. But, there were a lot of years where it was very dicey.

MS – So when you’re constantly hearing a“No” all the time and you keep learning and you keep moving forward, did you ever doubt that you made the right choice? How did you keep yourself motivated to keep pushing forward?

TB – You know, I didn’t and I don’t know why. I will make a case for having no sense – I don’t know that I had enough sense to be doubtful! Because there have been a number of occasions where I certainly should have. And the explanations were trickier and trickier with my wife more and more.

I’m trying to think of those 10 years. Those were years filled with very few successes, actually. One of which we pushed out to 20 states and that was completely overwhelming. And then pulled back to about eight. I think what those years did was get me in a position to partner with somebody, like we did with Seagram. And I would characterize that as falling uphill as much as anything else.

MS – That story resonates with me. I had been married for about three months and I still had the single mentality – “If I want to go out, I’ll go out.” I remember I was reading this book and there was this quote that said, “That in life that you fear the most is what you should most be doing.” So I had this business on the side, while I was doing my day job. And I walked into my bosses office and said, “Thank you, but I’m giving my notice.” And as soon as I walked out it hit me – I have not talked to my wife, I haven’t consulted with her!”

TB – That is a seriously bold move. I turn it back over; did you have your doubts?

MS – I did! I had fear, but I felt that anxiety came from a good place, because I was all in.

TB – I think fear is different than doubt. I’ll distinguish the two. Doubt is you just don’t think – “Maybe I should give this up. Maybe I should stop.” I never felt that for a minute. When people said, “Go to hell, Tom.” I never – I said, “We’re gonna do this. We’re gonna take the next step.”

Fear is a wonderful motivator. I probably shouldn’t say this but if I were honest about my primary motive, it is fear. I was married, had two children, the man of the family – that may be old fashioned – but there was an expectation that I would support my family and educate my children. My father, would’ve defined who he was by that. That’s what a father and a husband does. Fear makes you do that. Fear is a big deal.

I don’t think I know enough about myself to say how primal motivators work. But I’ll say this – I still have the same fear. It doesn’t go away. It’s been 29 years and it’s working, OK? But it doesn’t go away.

Be sure to check out part two of our interview with Tom next week and part three the following week.

For more information on the history of Bulleit Bourbon, visit