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How I Regained a Feeling of Significance After Selling My 27 Year Old Business

For today’s episode of The Exit, Steve McGarry sat down with a well-known entrepreneur guest, Jeff Wiener, about a topic that people rarely talk about – the post-acquisition. Selling a business or assets that are fruits of your time, utmost efforts, and money can be depressing and unmotivating. There would be a series of depression that you have to overcome after losing your cherished business.

Jeff Wiener is an entrepreneur who founded multiple companies while being a successful real estate investor and a best-selling author at a young age. Wiener loves to talk and educate people about running a business and investing, especially the mindset and behavior that a business owner should possess. Learn from his story about how his epiphany occurred and changed his career path.

Wiener’s Epiphany

At the young age of 16, Jeff Wiener already attained being a serial entrepreneur, selling the various businesses he built. Wiener started his second business while he was in college and sold it when he was around 19 to 20 years old. At 21, Wiener established and grew a large telecommunications company and ran it for 27 years but eventually sold it even with 55 employees.

It may sound unbelievable, but Wiener did not sell the telecommunications company because of profit issues, as the business is promisingly profitable. The daily grind of managing people and the scale of a company like Wiener’s has become tiring already. A 3-hour-long walk at the Florida beach last January 2017 gave an epiphany to him that there is more to life than running a business. Instead of a repetitive and monotonous routine, Wiener thought about expanding his business and called the M&A advisor to sell his 27-year business. He stepped down as president of the company in December 2017 as private equity bought the company and stayed for three years owning a minority.

Selling a Business is Not a Joke

As soon as Wiener decided to sell the company, he talked to Chris, an advisor, and he got bombarded by literally a hundred and fifty daunting tasks that he must do to put his company on the market. While his team was preparing to sell the company, Wiener also entailed how his business continued being operational along the way, whether it would get traded or not. Chris puts up a presentation about confidential matters on Wiener’s company and sent it to 50-60 companies until they began the bid with nine active bidders. Eventually, Wiener reached the deal in October 2017, with his last day as the company’s president on New Year’s Eve, December 31, 2017.

Perspective on Post-Acquisition

During the first day of his descent from the presidency, Wiener found himself in an extreme existential crisis as he felt lost about what he should do. He went through a significant adjustment from his daily routine for 27 years as a CEO until he convinced himself to become busy. Wiener finally found a purpose and wrote the book “The Kickass Entrepreneur’s Guide to Investing” that sold over 50,000 copies on Amazon. Pursuing his writing career, Wiener continued as a blogger (thekickassentrepreneur.com) while making videos and podcasts that received positive affirmations that brought essence to his life that he failed to received while running a business.

In August 2018, as Wiener became busy again with his life as an author and with his podcast, he realized that he is gradually returning to his old habits. Wiener thought of slowing down his pace to figure out the imperative things for him through documentation, only to realize that he is now okay with not running a business.

However, Wiener is still uncomfortable with the “retirement” talks as he still feels the need to be busy. He admitted that letting go of a business is a real challenge, not because of the financial aspects but due to the mental and emotional effects that he must deal with to satisfy himself fully. The existential threat is Wiener’s primary subject for contemplation, keeping him skeptical about what is his purpose in this world.

Finding an Outlet

Like moving on from a romantic relationship, the post-acquisition perspective for a former owner like Wiener is also displeasing and tedious. Thus, going through a rigorous change needs an “outlet” or something fulfilling to become preoccupied. In Wiener’s case, it is writing.

Writing became Wiener’s outlet because it enables him to release his chaotic and overwhelming thoughts while helping other business owners on the run and even those who have retired already. Some of his beneficial write-ups were about knowing whether a business owner should sell a company to the slightly personal updates every six months about his life. He also founded a non-profit organization named ICE Network, composed of former entrepreneurs (late 40s to 50s) who are now semi-retired and retired, where most of them are looking for their purpose.

Letting Go

Apart from writing blogs, making videos, and doing a podcast, Wiener recently started ICE Network in February 2020, a peer-to-peer group of entrepreneurs to help other entrepreneurs navigate the world of wealth, life, and succession planning. Wiener and his org mates also talk about investment opportunities and experiences as entrepreneurs who usually work 80 hours a week. He also becomes the president of an advertising and marketing site for early-stage entrepreneurs with startup business ideas and plans, marketing, funding, scaling, and growth to build a profitable business. He is also willing to impart his knowledge and struggles to serve as motivation and driving force to other entrepreneurs who failed their businesses.

Wiener also entailed how he wished that someone could tell his 10-year younger self that he is his business’s worst enemy like, “Hey Jeff, you are doing things that are holding your business back. You got to stop doing them.” He failed to recognize his mistakes, but gladly, it wasn’t too late yet. He was able to move past his point of incompetency and change his behavior. Fortunately, these experiences brought epiphany to him to avoid making his life rotate to business and find another purpose of his existence.

PODCAST TRANSCRIPT

Steve McGarry:

Hello and welcome to The Exit, presented by Flippa. I’m your co-host, Steve McGarry and this is a 30 minute podcast featuring amazing entrepreneurs who have been there and they have done it. They have exited businesses. They have bought businesses and they talk about the tricks and the tips that they have learned while operating those businesses.

Steve McGarry:

And before we dive into today’s episode with Jeff Wiener, an amazing entrepreneur, definitely check out my previous interview with Mark Andre, the co-founder of Vital Dollar. There’s some incredible content in there about scaling up content businesses and definitely be sure to check that out wherever you’re listening on your device, wherever you’re listening on Spotify, iTunes of Sound Cloud. It is worth the listen.

Steve McGarry:

So on this special episode, I sit down with Jeff Wiener to go over some of the really powerful things post-acquisition. Now, this is a topic that a lot of people don’t talk about and after you sell a business that you’ve been building for, let’s say 10 years, eight years, six years, five years, whatever it may be, there is a short period of time, some long periods of time for some people where there’s a layer of depression or a layer of lack of meaning that comes into the picture.

Steve McGarry:

You’ve been building something for a very long time and when you sell it, it does off into someone else’s hands and your baby, quote unquote, is passed over to a different parent. A lot of people struggle with this. I did myself, many people that I know that have sold very large scale businesses run into this because it takes a long time to build businesses up. So this is a very special episode in terms of the mindset post-acquisition and Jeff Wiener has founded multiple companies. He’s a real estate investor, best selling author and just overall really nice guy and it was fun to sit down and talk to him about his walks on the beach that are literally like epiphany after epiphany. Him walking on the beaches, which is really a great way of filtering things through your mind and sorting things out on your own.

Steve McGarry:

So without further ado, let’s jump into my interview with Jeff Wiener.

Steve McGarry:

What is up everyone? I am here with Jeff Wiener, the entrepreneur and investor. How you doing, Jeff?

Jeff Wiener:

Good morning. I’m great, Steve. How are you doing?

Steve McGarry:

I’m doing fantastic. I’m doing fantastic. So before we dive into just the psychology around what happens after an exit, let’s hear a little bit about your story. What’s your background and what brought you to sell your business?

Jeff Wiener:

Sure, so I’ve been a serial entrepreneur all my life. Started my first business at 16 and I started my second business while I was in college. Sold that at the age of about 19 or 20 and then started a telecom company when I was 21. And I ran that for 27 years. I grew the business to a fairly large size. We had about 55 employees by the time I sold it and I ended up selling that business not because it wasn’t profitable. It certainly was. The business did extremely well. But more because I got tired of running and business and I would say the daily grind of managing people, managing the scale of a business of that size, going to the office on a daily basis, managing warehouse and staff and everything else just kind of got to me and I came to the realization that there had to be more to life than running a business.

Jeff Wiener:

An actual fact, I was walking along the beach in south Florida in January of 2017 and I came to the realization at that point that … So I went for a long walk on the beach and while I was on the walk, I started the walk with the intention of figuring out how I was going to double the business yet again, because I had just come off a cycle of doubling the business. So we’re now in January 2017. After three hours of my walk in Florida, I’m thinking about what I need to do. Who I need to hire. Who I’m going to promote. We’re going to be moving office space. We need more warehouse. And had everything lined up and after about three hours of the walk, I came to the realization. I’m sitting there and I’m looking at the beach and I’m like, “I hate this. I don’t want to do it any longer.”

Jeff Wiener:

I went to the JW Marriott on the beach and I took out my phone, had a beer, and for the next three hours typed away on my phone and I generated notes on what I needed to do for the next stage of my life. The very next day I called the M&A Advisor and I advised them that I was no longer interested in running my business. Put it on the market in January of 2017. It was a fairly lengthy process. Took about 10 months, and by October 2017, I had exited. I stepped down as president at the end of December 2017 and that’s the quick story, I guess, of who I am and why I came to sell my business a few years ago.

Steve McGarry:

Nice. Nice. I love that. It all happened on a walk. It was all from…

Jeff Wiener:

It was an epiphany.

Steve McGarry:

An epiphany. Epiphany walking. Nice.

Jeff Wiener:

If you will, yes.

Steve McGarry:

Yeah, that’s fantastic. I love that you actually set out on the walk to think about doubling the business and it turns out that that was exiting, which is a fantastic way of looking at it, when you’re going on a walk, because everybody kind of has these zen zones that they go in to and they’re able to do at like the gym with headphones on, things like that, and it’s really cool that you did it while you were on a walk. So talk about the actual exit itself. What was … Whatever you can mention about the structure. If it was something a bit … Was it seller financing? Whatever you can mention about how that process was with Ernst & Young.

Jeff Wiener:

So I called E&Y, so come back from the beach. I’m at home. This is on a Sunday. Monday morning, I called Chris, is his name, the M&A Advisor from E&Y and I said to Chris, “I’m ready to sell.” It was Monday morning, it’s 8:00, whatever, first call of the day, “I’m ready to sell my business.” He says, “Jeff, what’s going on? Because we just spoke a few weeks ago and you said you’ve got another few years in you.” And I said, “Nope, done, ready. Get me out as fast as I can.” So we meet in early February and I go through the process and I meet with a number of different M&A Advisors and although E&Y was our accounting firm and they were doing our audits and everything else, it wasn’t … I mean, the presumption was that they were going to get the work, but I had to shop it around. So I talked to three different companies and I ended up going with them.

Jeff Wiener:

As part of the process, I had looked at, a few years prior, what was required in order to sell the business and E&Y gave me a list of, and I’m not exaggerating, 150 things that I needed to have done in order to sell my business. In other words having your accounting up to date. Having your accounts receivable, all of your KPIs properly outlined, but there were literally 150 … It was a 150 list document and it was daunting. But that document, in and of itself, gave me … And having it so far in advance gave me a long time in advance to get everything ready.

Jeff Wiener:

So when I was … A lot of those things are just best business practices in any event. Having proper HR policies and proper HR documentation, et cetera, et cetera. So when I told him I was ready to sell, I knew he was going to say to me, “Oh, by the way, you’ve got a lot of work ahead of you,” but in actual fact, we had done all that preparatory work well in advance and we were running our business, whether it was going to be sold or not, in a best practice fashion.

Jeff Wiener:

So all of those things that he was going to ask for are the best ways to run your business anyway. So when he started asking for data, we had it. Like here you go. Here you go. Here you go. Here you go. So he put together a confidential information memorandum or they did, anyway. It was probably, I don’t know, the document itself was a beautiful PowerPoint presentation, probably 80 pages long, and it detailed the business and everything else about it and they sent it out to I think at least 50 or 60 companies and we had about nine active bidders.

Jeff Wiener:

When we started the process in February of 2017, they explained that it would take and they laid out the outline or guideline of how long it would take to sell the business before I actually got the check and signed the document and they were pretty much on target almost to the day and they said, “Jeff you’re going to sell probably in sometime October 2017,” and it ended up closing in October of 2017. So it went on target and my company was bought by private equity. It was an eight figure deal and I walked away with a minority share in the business.

Steve McGarry:

Nice.

Jeff Wiener:

So and I committed to staying on board for another three more months and it wasn’t an [inaudible 00:09:09] it was I’ll stick around for three months. I’ll grow a new president and then I walked away in January 2018. The end of December, so New Years Eve, December 31, 2017 was officially my last day as president of my company.

Steve McGarry:

Wow, a fresh start.

Jeff Wiener:

A fresh start.

Steve McGarry:

That’s fantastic. So that’s a great segue into kind of after the acquisition. When we spoke before, we jumped on the show. We really were talking about some of the issues that a lot of people don’t cover when they’re talking about an exit. Like there’s this glamorous kind of high profile exit that a lot of people kind of dream of and they’re building this business, but a lot of the things that kind of go under the radar are the fact like, you’ve put years into this business that just goes in 10 months. It’s just poof, someone else’s business and you’re there for three months and then you have a fresh start. It sounds like yours was a very positive kind of fresh start, because you had a good size exit. You had a good private equity company that came in to take it over, so it wasn’t just going to fizzle out after the fact.

Steve McGarry:

So let’s talk a little bit about that. Your perspective on post-acquisition. Like what was it like for you?

Jeff Wiener:

So it’s January 8, 2018. So now I’ve got to fast forward one year later. I’m in Florida again and I’d finished my family vacation. My wife and my kids actually flew back to our home. I stuck around in Florida. We have a house there. My first day post-sale, first day as no longer president officially, I sit down. I’m looking at my computer screen and I’m thinking, “What the heck am I going to do?” I don’t have a job. I don’t have anyone reporting to me. I have real estate and I have other things going on in my life, but I needed a purpose and I didn’t have one. So I’m trying to figure out what to do. Again, I go back to the beach. Take a long walk one year later and I’m like, “Okay, what on earth am I going to do?” I started getting busy and I got busy with things. I wrote a book. The Kickass Entrepreneur’s Guide to Investing. It actually did very well. It sold over 50,000 copies on Amazon.

Steve McGarry:

Wow.

Jeff Wiener:

But I wrote a book. I started a blog. The Kickass Entrepreneur. I started writing. I started doing videos and I started … I had this need to get busy again and I would say about six months … It was like this existential crisis that I faced because I’d always been busy in my business. I always had a lineup of people waiting at my door. I had hundreds of emails, literally, hundreds of emails coming in on a daily basis. I had tons, like tons of stuff going on in my life and all of a sudden it’s done. And I had this need to be, what’s the right word? Significant. It was this feeling of significance that I had when I was president and it was missing and I had to get that feeling of significance back again, but I wasn’t running my old business.

Jeff Wiener:

So I started getting busy with other things and I was getting that feeling of significance from the positive affirmations from my book and my blog. I hadn’t started a podcast yet at this point. But I was so busy again that by August of 2018, I was stressed. I wasn’t sleeping. I’m like, “What the heck is going on? Why am I not sleeping?” And again, I came to the realization that I was trying to replicate, replace something that was missing in my life. So I slowed down and I said to myself, “I’ve got to stop. I’ve got to figure out what is important to me.”

Jeff Wiener:

I actually ended up reading the book, The Seven Habits of Highly Effective People by Stephen Covey and as a result of that, I documented and I laid out what are the most important things in my life? And I kind of crafted that and I’ve now moved into a new … So it sort of moved me into a new position where I was okay not to run a business. I was okay not to feel significant. I was okay not to make a lot of money running a business, because those were not the things that were important to me any longer and so I had to tell myself that it was okay for those things not to happen and for me to release that.

Steve McGarry:

Awesome. So you have had quite a few walks where you’ve had these epiphanies and really determined your future on a lot of these walks, which is super exciting and I love emphasizing that, because a lot of people, especially … We had Melissa Kaufman on the show and she talked a lot about the characteristics or I guess you could call them personality traits of entrepreneurs that always have to be doing a bunch of different things. I think that what you’re mentioning is super relevant to a lot of people out there. So let’s kind of pick up to after the acquisition, after you’ve talked about kind of coming to terms with the fact that you can somewhat retire, somewhat relax, and then pick up from The Kickass Entrepreneur blog.

Jeff Wiener:

Sure. You know, I don’t know that I’m ever … I haven’t really been comfortable with the notion of retiring. I need to be busy. I have an office at home and I sit down at my desk and I look at buying businesses. I look at being an angel investor and I make phone calls just almost to be busy and I almost made the decision to buy a business a few weeks ago, an online business, that was doing decent revenue and I got spooked. I’m like, “What am I doing? I’m going to be swamped. I’m going to be busy again and this is not what I want from my life.” So I pulled out my personal vision statement.

Jeff Wiener:

I actually keep a copy of it on my credenza and not that if I show you this piece of paper, you’re not … It looks blank, right? But I look at it often, because it’s a reminder for me of the things that are important in my life and when … Just as I was about to sign the paperwork for this business that I’m about to buy, I wasn’t sleeping again. I’m like what the heck am I doing? So I took that piece of paper out and I re-looked at it and I said, “The things that I value in my life and my personal vision statement, if you will, aren’t going to be reflected in the work that I’m going to be doing for the next year and a half running this business,” and I decided not to buy it.

Jeff Wiener:

So it’s been a bit of a challenge, to be perfectly frank with you, Steve. I’m not going to say that. Look, I love life. Financially my family is doing really well. I don’t have to work again. But I need a purpose and I’m trying to define that purpose and I always did as an entrepreneur. I always did as a business owner. I no longer am really that. I own businesses, but I don’t run them. So I provide guidance. I provide consulting. But there is something missing from my life and especially now that we can’t travel, which my wife and I were doing quite a bit of, it’s a bit of existential threat. I think I mentioned that earlier, of trying to figure out what is my place in this world and what do I do? Because I don’t want a job and I don’t want to run another business and I’m okay to be an investor, but I’m trying to find that spot that I’m completely comfortable in to find that purpose.

Jeff Wiener:

So I can’t say that I’ve figured it out, because I … And by the way, I don’t think we ever figure it out. I think we’re always trying to figure it out.

Steve McGarry:

That’s right.

Jeff Wiener:

But it’s a new purpose. It’s new for me, because when I was running my business, that was my purpose, and I did it for so many years I never had to ask myself, “What am I doing?” Because what I did was run a business. Now I don’t run a business. It’s a little different.

Steve McGarry:

Yeah. Yeah and that was something that we touched on in the Kaufman interview where being an entrepreneur is more of like an activity and a lot of people have very much made it part of their identity and it kind of consumes you fully when it’s your day in, day out, and she was comparing it to like an athlete. Athletes, that’s an activity that they do as a career and they have different attributes that make them a great athlete and very similar to young entrepreneurs and everybody getting into the buying and selling of websites, it’s very important to know that that is an activity and part of that is it takes a certain type of grit and personality to really continue to do that.

Steve McGarry:

I do love the concept of you blogging. I think that that’s really important for people to have an outlet after they have an exit and they’ve kind of passed their baby on to someone else. I think that having an outlet like a blog or a YouTube channel or anything like that could potentially have that little piece of purpose that you’re talking about. Have you found that with your Kickass Entrepreneur blog and…

Jeff Wiener:

Sure. So what I enjoy, it’s been fairly cathartic for me, because it allows me to formulate my own thoughts and I know that I’m helping other business owners and people who have retired or semi-retired or near selling their business, because I talk about all that stuff. Like how do you know when it’s time to sell your business? What’s life like after you sell your business? I write an update every six months. What is my life like? Because there’s a lot of entrepreneurs who have just sold, who are ready to sell. They want to know what life’s like.

Jeff Wiener:

I actually started an organization called the Ice Network and it’s comprised of former entrepreneurs who are now semi-retired, retired, most of them are in their late 40s, 50s, who are trying to find purpose. I mean, there’s some people in the group who have sold their business for big, big, big dollars and just because they have a lot of money doesn’t mean they’ve necessarily figured it out. So it’s … I mean, some of them are angel investors. Some of them are getting back into businesses themselves and we get together and we talk about, “Hey, what’s life like? What are you doing? What are you up to?” We talk about investment opportunities as well.

Jeff Wiener:

Being an entrepreneur is whoever’s done it and especially if they’ve been successful, or not, you come to realize it’s a life. It’s a huge challenge. It is difficult, grinding work. It’s not like you’re working 30 or 40 hours a week, most entrepreneurs are working 80 hours a week and they’re oftentimes they’re not making any money for the first few years and you’re grinding it out and you’re wondering, “What the heck am I doing this for?” And that’s why I think it’s … What’s the stat? I think 20% of startup businesses make it past five years in business and there’s a reason that so many of them go out of business. There’s so many elements of business that entrepreneurs don’t seem to get.

Steve McGarry:

Mm-hmm (affirmative).

Jeff Wiener:

You’ve got to get past those hurdles. It is a big challenge. It’s a lot of fun and if I had to do it all over again, I absolutely would, 100%, and I don’t think I could ever work for somebody. I am an entrepreneur at heart.

Steve McGarry:

Well said. Well said. So a question that I ask everybody on here, and this one is kind of a mind melter, is knowing what you know now, what would you tell Jeff 10 years ago?

Jeff Wiener:

That’s a really good question. What would I tell Jeff in 2010, what would my message to myself be? You know, I was floundering for quite a few years and my business was growing and it was doing well, but it’s kind of plateaued and I reached my … There’s a term in business called Peter Principle and I had reached it in probably 2008 and I didn’t realize it until I was slapped in the face by one of my favorite employees who quit in 2013. So I was running around for three years doing things in business that I didn’t realize I had become my business’ worst enemy and I wished someone had told me in 2008, 2009, 2010, “Hey Jeff, you’re doing things that are holding your business back. You’ve got to stop doing them.”

Jeff Wiener:

And until one of my employees slapped me in the face and said, “You’re doing things that are holding your business back. You’ve got to stop doing them.” No one told me. I guess it’s like the emperor has no clothes, no one wants to tell the emperor they have no clothes. So someone actually told me and as a result of that, I ended up moving past my point of incompetence. I changed my behavior and some of the ways I was doing things and I learned to become more of a leader rather than a manager and to lead people and from there, the business truly flourished. It did really well when I started leading as opposed to managing or [inaudible 00:21:39] on the business, not in the business. I changed my attitude towards it and I created a game plan and developed that growth pattern and plan that I had.

Jeff Wiener:

So I wished I had found that out sooner.

Steve McGarry:

Well said. Very nice. All right, so that’s all the questions I have. Where can people go learn about your book and learn more about your journey?

Jeff Wiener:

So you could find me on my website, thekickassentrepreneur.com. I also have a podcast. You can find that at The Small Business Millionaire. You can find it on Apple and Google Podcast and feel free to reach out to me. If you’re reading my blog and you have some questions, I’d love to hear from you.

Steve McGarry:

Fantastic. Well, if you guys are listening in on iTunes or Spotify or watching on YouTube, all of what Jeff just mentioned, all the links will be in the show notes and once again, thank you so much for coming on the show, Jeff.

Jeff Wiener:

Great to meet you, Steve. Thanks a lot.

Steve McGarry:

Thank you so much for sticking around to the end of this episode of The Exit presented by Flippa. Like I said before, the links will be in the description below, so you can check out what Jeff Wiener’s working on. He’s doing some incredible content out there. Really trying to focus on helping people and just searching for his next kind of venture out there. So really great information in this episode. I hope that if anybody out there is struggling after … Post-acquisition, definitely leave a comment or reach out to us directly. There are a lot of resources out there that can help you find another niche, another piece of content to write about. Another topic. And I highly recommend that people find something to really find fulfilling and write about, because writing, creating content, from someone who is a full time content creator and I love creating content, I think that that is a really great thing to have as an outlet for people post-acquisition.

Steve McGarry:

So that’s my two cents and this was an incredible interview touching on a subject that not many people touch on, so we were all really excited for this one and if you guys liked it, please smash the like button. Don’t forget to be subscribed, because we have some amazing interviews coming in the next couple of days and weeks and I will see you guys on the next episode of The Exit.

Steve McGarry

Steve McGarry

Steve McGarry is an entrepreneur, content creator, and investor based in sunny Tampa, Florida. In 2015, while living in San Francisco, Steve sold his first fintech startup LendLayer to Max Levchin’s (founder of PayPal) consumer finance company Affirm. In the last 5 years, Steve has both built an online community that reaches 1.4 million people every month on social media and a portfolio of over a dozen web properties. Currently, he’s the co-founder of a next-generation fintech startup called GrowYourBase while managing his portfolio of online businesses.