Jessica Fialkovich | Starting a High-End Wine Business From Scratch and How To Buy and Sell Businesses — Even in a Down Economy
Smart Business Revolution

Jessica Fialkovich is the Founder of Exit Factor, a firm that teaches entrepreneurs how to build and sell their small and mid-size businesses through online programs and one-to-one consulting services. She is also an author, a certified speaker, and a small business advocate. Jessica is the Co-owner of Transworld Business Advisors which focuses on business brokerage, franchise consulting, and franchise development. An entrepreneur at heart, she is a four-time Inc. 5000 honoree and award-winning entrepreneur recognized by Inc. Magazine, The Financial Times, Denver Business Journal, and ColoradoBiz Magazine.

Jessica is also a member of Entrepreneurs’ Organization (EO), the co-host of The Deal Board Podcast, and the co-author of Getting the Most for Selling Your Business: How to Get Top Dollar for the Company You’ve Nurtured for Years.

In this episode of the Smart Business Revolution Podcast, John Corcoran interviews Jessica Fialkovich, the Founder of Exit Factor, about preparing a business for sale. They also talk about Jessica’s experience building a high-end wine business, her tips for developing a successful business brokerage firm, and how she helps other entrepreneurs sell and exit their businesses.

Available_Black copy
Available_Black copy
Available_Black copy

Here’s a Glimpse of What You’ll Hear:

  • Jessica Fialkovich talks about her family’s entrepreneurial journey and how it influenced her life
  • How Jessica built a high-end wine shop during a recession
  • The challenges Jessica faced growing her business, why she sold it, and her key takeaways from the experience
  • Jessica’s inspiration to help small business owners buy and sell companies
  • How Jessica became a Transworld Business Advisors franchise owner
  • Why does Jessica maintain a physical office presence?
  • Jessica’s strategy for maximizing a business’ value during a sales transaction
  • Current trends in the business brokerage industry
  • How Jessica manages multiple businesses
  • Jessica’s mentors and contact details

Resources Mentioned In This Episode

Sponsor: Rise25

At Rise25, we’re committed to helping you connect with your Dream 100 referral partners, clients, and strategic partners through our done-for-you podcast solution. 

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses build strong relationships with referral partners, clients, and audiences without doing the hard work.

What do you need to start a podcast?

When you use our proven system, all you need is an idea and a voice. We handle the strategy, production, and distribution – you just need to show up and talk.

The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI, which is the most important component. Plus, our podcast production company takes any heavy lifting of production and distribution off your plate.

We make distribution easy

We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Google Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPO, EO, Lending Tree, Freshdesk,  and many more.  

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

Are you considering launching a podcast to acquire partnerships, clients, and referrals? Would you like to work with a podcast agency that wants you to win? 

Contact us now at [email protected] or book a call at

Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

Episode Transcript

Intro 0:14

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

All right, welcome everyone. John Corcoran here, host of this show. And if you’re new to the program, you know, check out our archives, we’ve got all kinds of great interviews with smart CEOs, founders and entrepreneurs of companies ranging from Netflix to Kinkos, YPO, EO, Activision Blizzard, LendingTree, OpenTable, and many more. And I’m also the co-founder of Rise25, where we help connect b2b business owners to their ideal prospects. And my guest here today is Jessica Fialkovich. I saw her speaking at the EO Alchemy conference that I attended earlier this year. And she gave a great presentation on how to exit your business and she is an expert on exiting your business. She’s an author speaker, small business advocate, award winning business owner. She’s the Founder of Exit Factor and also the Co-owner of Transworld Business Advisors, which has offices all over the United States. She’s an entrepreneur at heart, grew up in an entrepreneurial family, we’ll talk about what she learned from her grandparents who owned a business. And she’s also active in EO Entrepreneurs Organization, which is how we connected and the co-host of The Deal Board podcast. So go check that out. And her book is Getting the Most for Selling Your Business: How to Get Top Dollar for the Company You’ve Nurtured for Years.

And of course, this is brought to you by Rise25, my company, where we help b2b businesses to get clients, referrals, and strategic partnerships with done-for-you podcasts and content marketing. And you can learn more about what we do at All right, Jessica, pleasure to have you here today. And my grandfather was a lifelong Air Force person, he grew up in the Depression. And that experience interesting how, you know, the experience of different generations flows down to affect subsequent generations. So he was a child of the Depression. And because of the instability growing up and having, you know, to make money as a kid just to pay the bills, he went into the most stable thing he could find, which was the military for his entire career. Wow. And you have the experience, your grandparents are actually were entrepreneurs actually built up a chain of pharmacies tell me what that was like?

Jessica Fialkovich 2:43

Yeah, so it actually started back like, I think my great great grandparents got started. Their first business was bootlegging, we’re from New Jersey, so that’s kind of like, you know, part of the course. That’s awesome. So my grandfather was actually a third generation entrepreneur, his parents owned bars and clubs and out of Trenton, New Jersey, but he was military too. So he his journey started that he entered the military and he was stationed on on Pearl Harbor after the attack, fortunately, but he was stationed in the men, med bay and sickbay. And he got professional training as a pharmacist. So when the war ended, he uses some some of his benefits. And he had known one of the the local pharmacy owners when he was growing up, and he would kind of work the store shelves for the him during school and stuff like that. So he uses benefits to buy that pharmacy owner out and that was his first location. It was called Pryor’s pharmacy, located just out of Washington Crossing Pennsylvania, and that’s how he got his start. So really was more of a pharmacist like technician turn business owner, but he did have his parents and his grandparents to learn from, from that entrepreneurial kind of gene that travels through the family.

John Corcoran 3:59

And they built it up to a couple of different locations and numbers. Yeah, so he actually he

Jessica Fialkovich 4:03

he grew through acquisition, you know, back in the 60s and 70s, probably before it was popular, so bought a few more out started his one of his own, I think at the height they’d four locations, all in that Washington’s crossing Morrisville area of Pennsylvania, like Bucks County area.

John Corcoran 4:22

How much do you think because you’ve done this now in your career, but it’s not so strange. It’s like, it’s like what the family does. How much do you think that has affected your attitude? Because you’re you’re relatively young, you’ve accomplished a lot. You know, for many business owners, that’s intimidating. But do you think that because you grew up around it, it was less so?

Jessica Fialkovich 4:43

Um, it’s interesting because I didn’t like I didn’t grow up around it my entire life. So my grandfather, it’s actually a pretty sad story. But so after he built it up, he waited too long to exit the businesses and in the northeast, you know, in the eight 80s and 90s these chains like CVS and egrets came in and it really started eating market share from him and causing a lot of stress and anxiety on his family. My dad in particular, so my dad watched that roller coaster that small business owners travel. And so he ended up selling out for pennies on the dollar are way too late in the game, and it really ate away from all the equity, he built up his retirement savings. And in the end, he passed away fairly young. You know, I don’t know if it was from a broken heart or what, but he had to go back and work for those corporate giants that he hated. So it was interesting. So I saw it as a young child, and then he passed away when I was just 12. So the influence I mostly got was from my parents. And the like, the overwhelming resounding message that I got from my dad was enter a career that’s super stable, get a good job, good benefits, pension programs. So my dad entered the education system, he was a school administrator for his entire career, super safe job, first generation in, you know, four to skip that entrepreneurial path. But so that’s what I grew up around. And it really wasn’t until I got into entrepreneurship, and my my sister’s an entrepreneur too, until we took that path where my dad was, like, what happened, like I raised you guys not to do this. And then the whole story of my grandparents came out, and I kind of like have buzzy memories of the pharmacies and stuff. But I was super young. So it’s funny, it’s like, I don’t know, maybe it’s more genetic, more, you know, nature versus nurture. But it is funny when I talk to my dad now and he’s like, I raised you guys not to go down this path. But my parents did. And two of my three daughters went down this owning your own business path.

John Corcoran 6:52

So it must have been hard for your father growing up around that and seeing that whole thing unwind. Who was he relatively young when that was happening?

Jessica Fialkovich 7:03

It was it was pretty much through his whole childhood. Right. So there was, you know, there was peaks and valleys and probably more valleys, towards like my father’s high school and college years. And as he was, you know, leaving college and starting his family, but yeah, you know, when we talk about it, it’s just like, it was just very up and down. And some years are great. And some years are terrible. And there was a lot of stress and anxiety. He, my dad just didn’t want that for his life.

John Corcoran 7:29

So for you, once you got into the working world, you actually were working in marketing for the Philadelphia Eagles and flyers, before you got into entrepreneurship, and relatively natural path went straight from working for a professional sports organization to opening a wine shop. How did that come about?

Jessica Fialkovich 7:47

Yeah, there was like, there was also a pause in there to where I worked for a big commercial real estate developer in New York. So and that’s how I met my husband and everything. But it was during the 2008 crisis. So we were with the commercial real estate development mitten company at that time, funding and commercial real estate. Yeah. And we were funded by this little bank, no one heard of called Lehman Brothers. So we know how that story ends. Fortunately, we did get a bit of a runway of we knew the layoffs were coming. And we were able to prepare for that for about eight months. And my husband also grew up in an entrepreneurial family. So his parents were in wholesale seafood out of Philadelphia, and he was groomed to own a company, right. So his whole thing was go learn corporate for a few years, and then I’m gonna go do my own thing.

John Corcoran 8:37

So yeah, he never did that and never went into the family business. No, that’s

Jessica Fialkovich 8:41

a whole separate story.

John Corcoran 8:44

I’m gonna have to interview him. Yeah. So

Jessica Fialkovich 8:47

um, so when 2008 hit, and we were looking at layoffs, like we both had this conversation of, you know, I was groomed for this super safe career that if I worked for a big company, I would, my future would be secure. And the realization I had was that was absolutely the least secure path I chose because here’s some dude in some New York highrise that has no idea who I am. And he’s just slashing budgets, right. And I’m just a list on a spreadsheet, like I have no say or control over that situation. So our friends had owned a super cool little boutique wine shop, that at that time, we were making frequent trips to the wine store, and it was just in New York. This is actually releasing in Aspen, Colorado, we’re doing a redevelopment project for them out there. And so we’re at the Aspen wine stores called grape and grain still there fairly frequently through this period. And one day we’re like, why don’t we just start a wine shop? Like why don’t we just do a grape and green does but we’ll do it somewhere warmer, and we’ll do it some more differently. And so that was about as much thought as we had into the into the marketplace. We picked Naples, Florida one because it’s one of the The largest wine luxury markets in the country. And to my inlaws had a house in a boat there that they weren’t using. So good for startup low overhead, right? Yeah. And yeah, and we were off and running within. Probably like, I’d say, within two weeks of our our layoffs that we knew were coming, we were on the road and forming our business operation in Florida.