The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Marketing/Creative Entrepreneur
Creative Entrepreneur artwork

Break Free from Golden Handcuffs: How John Cerasani Made a 2000% Raise and Built a Life on His Own Terms

Creative Entrepreneur · 2025-09-24 · 29 min

0:00--:--

Key moments - from our scoring

Substance score

28 / 100

Five dimensions, 20 points each

Insight Density5 / 20
Originality4 / 20
Guest Caliber10 / 20
Specificity & Evidence6 / 20
Conversational Craft3 / 20

John Cerasani, host of the "2000% Raise" podcast and forthcoming author, challenges the conventional wisdom that keeps talented professionals trapped in corporate careers. He draws on his own experience at Arthur J. Gallagher - a major B2B insurance brokerage - where he realized he could deliver identical client value independently while capturing the full economic upside. The core problem he identifies is what the hosts call "golden handcuffs": benefits, pension expectations, and lifestyle inflation that psychologically bind employees to corporate structures, especially when surrounded by peers without entrepreneurial drive. Cerasani's framework centers on calculating your runway before launch - how many months of savings you need to survive the early business phase - and the importance of replacing your existing salary with client revenue before quitting. He also emphasizes the ethical boundary between keeping a day job and building a side business: there's an "eclipse point" where conflicting time commitments become untenable, and reaching that problem is actually a good sign. For those in unrelated fields (coaching, publishing, design), he recommends starting part-time while employed. The conversation also touches on his post-exit evolution as a venture capitalist evaluating founders and emerging markets like sports gambling and cannabis, illustrating how entrepreneurial thinking extends beyond one exit.

Key takeaways

  • →Corporate salary growth typically matches cost-of-living adjustments unless you switch employers, making the only real alternative to escape the salary ceiling to start your own company.
  • →You need 6-12 months of runway savings before leaving your job, and should calculate how long it takes to replace your existing salary through new client revenue before launching full-time.
  • →The "eclipse point" where your side business demands more time than your job allows is actually the good problem to have - it signals product-market fit and means it's time to commit fully.
  • →Golden handcuffs (benefits, pensions, lifestyle inflation, and surrounding yourself with risk-averse peers) keep talented people trapped in careers they don't enjoy and looking forward to retirement instead of their daily work.
  • →Building a company to sell isn't necessary for success; Cerasani built his insurance firm to serve clients and generate income, but when private equity entered the market, the valuation multiple made an exit attractive.

In this episode

  1. 1The Golden Handcuffs: Why People Stay in Corporate Jobs
  2. 2How John Left Corporate Insurance and Built His Own Company
  3. 3The 2000% Raise: More Than Just Money
  4. 4Building Runway and Starting a Business the Right Way
  5. 5The Ethical Transition: When to Quit Your Day Job
  6. 6Private Equity Exit and Life After the Windfall
  7. 7Venture Capital and Finding New Opportunities

Mentioned

John CerasaniArthur J. GallagherState FarmShark TankFanDuelCaesar's PalaceNorthwestern

Guests

John Cerasani

Topics in this episode

Venture capitalGolden handcuffsArthur J. Gallagher2000% Raise podcastPrivate equity roll-upSports gamblingCannabis legalizationShark Tank modelW2 employmentCorporate insurance brokerage

Questions this episode answers

How long should you build runway before quitting your job to start a business?

Cerasani recommends giving yourself 6-12 months of runway (living expenses savings) before launch, with the bare minimum being 4 months of disposable income stretched to 7-8 months if needed. This buffer lets you make mistakes early without panic.

How do you know when to quit a side business and go full-time?

The "eclipse point" arrives when your side business demands so much time during work hours that it becomes ethically questionable to still be employed elsewhere; reaching this threshold means you have product-market fit and should commit full-time to your own business.

What prevents people from leaving corporate jobs despite unhappiness?

Golden handcuffs - benefits, pensions, summers off (for teachers), lifestyle inflation from regular raises, and surrounding yourself with peers who lack entrepreneurial confidence - create psychological barriers that keep people focused on retirement rather than enjoying their daily work.

How did John Cerasani calculate if he could succeed starting his own insurance firm?

He looked at his existing client relationships and revenue value from his previous job, then calculated how many clients he'd need to replace his salary (e.g., 12 clients worth X per year to break even), then estimated how long it would take to acquire those clients - roughly 1.5 years.

What happened when John asked for a raise before quitting his job?

Arthur J. Gallagher rejected his raise request citing cultural hierarchy concerns (a 27-year-old making more than 40-year-olds), but he later realized this rejection was actually fortunate because a higher salary would have created lifestyle inflation that kept him from ever leaving.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

5 / 20

The episode rarely rises above standard entrepreneurship platitudes - save a runway, stay in your industry, build equity in yourself. The one mildly interesting structural observation about the 'eclipse' moment is fleeting and undeveloped, and the flagship '2000% raise' concept is never quantified or explained mechanically.

corporate. Um, America has what I believe has brainwashed all of us to feel like you can't be an entrepreneur
at some point there's going to be an eclipse where it starts to become almost unethical. You know what I mean? Like, okay, you got to make a decision

Originality

4 / 20

Every major idea - golden handcuffs, don't take career advice from employees, stay in your lane when starting a business, side-hustle before quitting - is a well-worn entrepreneurship cliché with no first-principles framing or contrarian edge. Nothing here would surprise a reader of any mainstream business book.

you're surrounded by people that don't have that entrepreneurial spirit in them because they're they're employees just like them
you don't, you know, if you have...worked at a PR agency, you don't turn around, you know, start a nail salon

Guest Caliber

10 / 20

Cerasani is a legitimate practitioner - he built a B2B insurance business over roughly a decade and exited via a private equity roll-up - which gives him real credibility. However, the conversation extracts almost none of that hard-won operational knowledge, leaving him sounding like a generic lifestyle-entrepreneurship personality.

in my case it was called a private equity roll up approach where they were buying other...smaller insurance companies up, enrolling them into their organization
they basically bought us for like 12. It would have taken me 12 more years to make what I made in the one transaction

Specificity & Evidence

6 / 20

A handful of concrete anchors exist - Arthur J. Gallagher is named, the private equity roll-up mechanic is briefly described, and a rough client-count payback model is sketched - but the headline claim of a '2000% raise' is never numerically substantiated, and most assertions stay at the level of hand-waving abstraction.

I landed a job when I was 25 years old. I left the company I was at to go to go work with this insurance giant called Arthur J. Gallagher
our clients are worth X per year. If I get 12 clients, I'll be breaking even. How long is it going to take me to get 12 CL clients? Maybe a year and a half

Conversational Craft

3 / 20

The host relies almost entirely on affirmations, leading statements, and personal anecdotes rather than probing questions; a lengthy segment is consumed debating the guest's age. There is zero pushback on any claim, and the true/false question about whether entrepreneurship is easy represents the analytical ceiling of the interview.

Well, true or false. This is a. Being an entrepreneur is easy.
He's tan, got the world at his palm. He's calling his own shots. Seriously.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker C66%
  • Speaker B29%
  • Speaker A4%

Most-used words

money22life19state15start15raise15farm12insurance12clients10idea10making9john9entrepreneur9equity9love8family8entrepreneurs8

Full transcript

29 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: From college send offs to retirement dreams, life is filled with many important milestones. And making sure you have a plan in place to protect the people you love can give you confidence for whatever comes next. State Farm Life Insurance can help protect your family's financial well being through life's milestones. Your State Farm agent can help you choose flexible coverage. You can, uh, adjust as your family's needs change. Contact your local State Farm agent today. Like a good neighbor, State Farm is there.

Speaker B: We are creative entrepreneurs and we also know how difficult it can be to navigate the journey of entrepreneurship. Today you are going to unite with other creatives. Let's step out of this isolating experience as business owners, as authors, as podcasters or speakers. And let's start learning actionable tools you need to build an explosive brand. Let's start creating now. On with the show. If you don't know your soft worth, you need to know John Cerrasani. Because he knows what you're worth, what he's worth, what we're all worth. And we are often so afraid to ask for more. We'll dive a little bit deeper into this, but it's so true. We feel that we cannot ask for more. We cannot ask for more money, more perks, more benefits. But we have John Sarasani here. He is the host of 2000% raise. He has a book coming out in the near future, which I am definitely going to pre order when it comes out. You can learn all about him in the show Notes John Cerrasani. I betcha he's a lot to say today. Maybe or maybe not. Look at him. He's not come to come together.

Speaker C: I didn't know if that was my cue or not.

Speaker B: That is your cue.

Speaker C: I m am excited to be there. I'm. I'm watching you through the video screen. It look like you're still going to say something. Um, you know, my intros are usually much longer. Jules, I'm.

Speaker B: Well, you know what I'm going to do? I will. I will re record the intro and you'll be blown away. I'll just talk for 10 minutes. All about. It's all about John Sarasani.

Speaker C: I was totally kidding. And you don't, uh, need to rerecord any of that. Even this part right now.

Speaker B: He's awesome.

Speaker C: Um, yeah, he's awesome.

Speaker B: He's tan, got the world at his palm. He's calling his own shots. Seriously.

Speaker C: Tell us a little bit about this percent raise. The concept is actually that. Yeah, it's so difficult in corporate America. To climb that salary ladder.

Speaker B: Oh yeah.

Speaker C: At a pace that's any faster than cost of living adjustments from one year to the next.

Speaker B: That sucks. That's a sucky place to be.

Speaker C: It's truth, isn't it? It's the truth. And you know, unfortunately, to get a substantial raise in corporate America, you typically need to switch employers, you need to work somewhere else, and then maybe you go back to that other employer, you're doing the exact same job four years later for, you know, double the, double the salary, who knows? But my concept is that hey, if you, if you really want to do this the right way, here's the roadmap into going to, going into business for yourself and corporate. Um, America has what I believe has brainwashed all of us to feel like you can't be an entrepreneur, you can't compete. And typically I'm talking about the business to business environment you need to. The clients only want to work with the corporate giants. They have 20,000 employees, 50 offices. You know, if you go out on your own, you'll never be able to compete with them. Um, and it's, it's just not the case. Um, and I use my, my past as a, as a guide. I, I did just that.

Speaker B: I mean, you're a smart guy. Northwestern, correct?

Speaker C: That is correct.

Speaker B: Look at the research my team did.

Speaker C: That is incredible.

Speaker B: Google, Google is my team. But, you know, so you're a smart guy. You started building your professional acumen at an early age. What was the onus for you to say I can't do this no more?

Speaker C: You know, I was fortunate. I work, um, the insurance industry group and corporate insurance. So it wasn't like selling life insurance or individual policies was the bigger, you know, business to business kind of side of it. And I landed a job when I was 25 years old. I left the company I was at to go to go work with this insurance giant called Arthur J. Gallagher. And I have this perception. Shout out, yeah, Arthur J. Gallagher. They're big, they're billion dollar fortune, you know, uh, publicly traded company, they're big time. But I gotta tell you, I was so excited to get that damn job there. And I was under this, um, I don't know, I guess like uh, the smoke and mirrors of thinking that there was like something magically that happened there that they were doing for their clients. You know, oh gosh, I'm gonna learn all these hot secrets, I'm gonna. And then you get there and you learn they're just doing the exact same thing everyone else is. But, but as an industry we've, we've developed this perception, um, that really isn't reality. At the end of the day, the deliverables for the client was the exact same thing I was given to my clients at the other place. And um, after working there for a few years I'm like, you know what? I could give these same deliverables to my clients working for myself, put myself on top of the org chart and built equity in myself versus somebody, somebody else. And you know, that's where Ah, the 2000% raise, uh, raise came in. And even more important than just the year to year financial piece, you're, you're building freedom for yourself when you own your own company and you're also putting um, you know, you're building something you could sell at the end. Um,

Speaker B: well, true or false. This is a. Being an entrepreneur is easy.

Speaker C: True or false, I would say. Gosh, that's, that's a, that's a black and white question, isn't it? I'm going to go with false if I have to answer one or the other.

Speaker B: Well, you have to have a certain kind of grit and resilience to be an entrepreneur. Because I do work with a lot of entrepreneurs who, who give up at ah, month six year one because they're not seeing the ROI and what they're giving out.

Speaker C: Right, exactly. And the long term benefit, um, that you really don't always see very clearly in the beginning is tough. And if you got bills to pay, walking away from, you know, it's, it's not just what it's costing you right this second, it's the opportunity cost if you're losing money. Not only am I losing a couple grand a month or whatever, I'm also losing the $90,000 I might be making working for someone else right now. You know, it's um, it's a tough pill to swallow. So people got to go into that with their eyes wide open. Most certainly.

Speaker B: Well, I don't, that's why I don't think a lot of people do it because they are handcuffed, you know, handcuffed to benefits, handcuffed to consistency.

Speaker C: Yeah.

Speaker B: But it's so much more exhilarating doing things on your own and being creative and figuring it all out.

Speaker C: That's so true. And another thing is, you know, not only they're handcuffed, you call them the golden handcuffs.

Speaker B: Golden handcuffs, Correct.

Speaker C: Certainly. And the issue on top of it is they're surrounded by people that don't have that entrepreneurial spirit in them because they're they're employees just like them. Oftentimes W2 employees and.

Speaker B: Mhm.

Speaker C: It might be someone you look up to in your office. Okay. You know what? I really respect that guy. He's my boss.

Speaker B: Or I love the managers. I heard managers.

Speaker C: I'm going to be the regional vice president. One a day and I'm going to go. Thank you. Exactly. Maybe what is it? The uh, the assistant. The assistant to the manager or whatever? Um, yeah, exactly. But I gotta tell you though, you know, the mistake people make is they'll go to those people for guidance or advice. You share your idea. Say, you know, say you're 30 years old and you're looking up to a person that's been there longer, say in their 40s or 50s, and you ask them their advice on this idea you got. What? One, they can't say it's a good idea because then they would be saying that this, this person that's, you know, below me on the totem pole is going to jump way, way ahead of me. And you know, they're not going to say it if they do think it, but chances are they don't even think it anyway because they're scared to do it themselves.

Speaker B: So true. So true. And even me taking that step into the land of being an entrepreneur, I had the safety net of a husband who makes a decent income. So it wasn't as risky for me. But a lot of people that I

Speaker A: do planning for the future State Farm can help because they know life's biggest moments often come with big responsibilities. Whether you're starting a family or buying your first home, State Farm life insurance can help protect those you love. With flexible coverage options that fit your budget, plus the ability to update your life insurance policy as needs change, you can live more confidently as life changes. Get started with State Farm. Like a good neighbor, State Farm is

Speaker B: there you talk to. They are so afraid because it comes down to the money, money, money. But I say from right now, John, to the last breath you take, is this how you want to be living

Speaker C: your life right now? Oh, most certainly.

Speaker B: Well now. But like let's you know, or Mary or Sue or Tom.

Speaker C: Well, and I gotta tell you, that's something I get into in my book quite a bit. It's like look at all this time you're spe spending. What, what are you looking forward to? You're looking forward to your vacation, you're looking forward to retirement one day. You're looking forward to, you know, retirement.

Speaker B: You're in retirement, aren't you?

Speaker C: Sort of Boring.

Speaker B: But you're not, you're not, you're shaking retirement up.

Speaker C: But you know, it's, I got a lot of friends and I got a lot of people in my family that are public school teachers and in the state saying, you know what? And in the state of Illinois, you know, if you're the right school districts, you get, you get paid pretty well. But they're still waiting. Okay. You know why they're doing it? Because they get to retire early, because they have summers off.

Speaker B: Got a pension.

Speaker C: Well, exactly. But it's all these things that don't involve their job is going to work each day. And, and don't, don't take me wrong. And they're also there for the right reasons. But when you hear them talk about the great things about their job, oftentimes they're talking about the other things I said, those kinds of perks. Okay.

Speaker B: Mhm.

Speaker C: Versus, versus an entrepreneur that could actually control his own destiny. I'm excited to go into the office each day. What's going to happen next? You know, um, what am I going to learn from one of my clients? So it's uh, I always just encourage people to say, you know, hey, you're spending a lot of time on this earth as uh, you know, working and

Speaker B: um, you know, working for the man.

Speaker C: Find a job you actually like. You know what I mean? If all you're worried about is looking forward to retirement one day, that's, that doesn't mean you really like your job very much.

Speaker B: I know. And then, you know, you get in your 40s, 50s, and there's no, people think there's no turning back from that age point, you know, that I've done it for 20 years, I'm gonna do it for 20 more years.

Speaker C: Yep, yep. I, uh, one of, one of my chapters in the books, book talks about that. And, and I, I use myself as an example. I, I, before I quit my job, I went and asked for a raise. And it was a substantial raise. And um, I was hoping they'd give it to me, but now that I look back, thank God they didn't give it to me. Yeah, they said no. They said, I just can't do it. Listen, I was making, I was 27 years old. The environment there at the time was almost like a hierarchy and for them it just wouldn't have looked right in the culture of a 27 year old was making more than 40 year olds and blah, blah, blah and whatever. God, God bless them, it's a great company. And I think they changed that model nowadays anyway. But, but the, the thing is I'm really thanking them for not giving me that raise because if had they given me that raise, I might not ever left. You know, I probably wouldn't have. And why is that? Because that salary goes up, I buy more things with it, I have more obligations with it. I get used to that lifestyle.

Speaker B: You got a new car.

Speaker C: Yeah, exactly. And now you got to walk away. And then as an entrepreneur, most entrepreneurs should be looking at this. I surely did. How long is it going to take me to replace my existing salary when I go out on my own? Okay.

Speaker B: And the bigger answer though, I feel like, I feel like that's an um, answer you can't really quantify because you don't know.

Speaker C: Well, for me it was quantifiable in the sense because I was leaving to go into the same industry. So I could kind of look at it, you know what I mean? I could look at it and say, okay, you know, our clients are worth X per year. If I get 12 clients, I'll be breaking even. How long is it going to take me to get 12 CL clients? Maybe a year and a half, you know what I mean? So, so I did the numbers like that. But, but you're absolutely right. If, if you're just saying, hey, I'm out of here.

Speaker A: And from college send offs to retirement dreams, life is filled with many important milestones. And making sure you have a plan in place to protect the people you love can give you confidence for whatever comes next. State Farm life insurance can help protect your family's financial well being through life's milestones. Your State Farm agent can help you choose flexible coverage. You can adjust as your family's needs change. Contact your local State Farm agent today. Like a good neighbor. State Farm is there.

Speaker C: I'm leaving my accounting job to open up a pizza franchise. Then you know, you might have uh, a more difficult time figuring that out.

Speaker B: It's a lot. And I don't know if you know this about me now. I did the research on John before he came onto this show, came into the studio, the Mediacaster studio. But I have written two books on how to start a business, how to be an entrepreneur. And I really wrote it as a guidebook for all my clients because I was telling them the same things over and over again. I'm like, here, grab my book. But it, there is so much involved and if you're going into the same business insurance or you know, starting a business franchise pizza parlor, it's kind of pre made for you but what if you're starting a coaching business or you want to start a publishing business or writing books or being a graphic designer? What is your best advice for those people?

Speaker C: Yeah, you know, I always think if you're mature in your career, like as a few, as you've been over 40. Okay. Yeah. And, and really just anyone that's just working, that's relying on their, their salary right now, um, I recommend giving, you know, give yourself some Runway so, so you can make some mistakes. You know what I mean? If, if you're, if you're, uh, you know, disposable income, savings, uh, account stretches out to last you four months right now, maybe, maybe tighten up an extra year. And yeah, that's a seven or eight months before you, you launch it, Launch the business. Um, you know, so, you know, and I think a lot of people too. Yeah. I mean, it depends what they are, but some of the things you just named, you could potentially start those out part time or as a side hustle before it turns into a career too, right?

Speaker B: Oh, my God. I never recommend someone just to say, zionara, I'm starting a job, I'm starting my new business tomorrow, and I have no idea, uh, what the heck I'm doing. You know, you have to be smart about it. Don't be stupid. Stupid.

Speaker C: Well, I, I gotta tell you, and, and, and when you do start that other, when you keep your job and you're doing something else, all right, I, I believe, because at some point there's going to be an eclipse of where you're spending your time. And from an ethical standpoint, you know, you work as, say you're some W2 job and you're getting paid X, and during launch and every, you know, hour at your work computer, you're checking your other business. At some point, there's going to be an eclipse where it starts to become almost unethical. You know what I mean? Like, okay, you got to make a decision and you shouldn't really be working there anymore and you should quit your job and focus full time here. And you know, I, I, I tell people that's, that's, that's the problem you want to have when you get to that point. That's the good problem to have, Right?

Speaker B: No, I love that. And you know, one, uh, particular person I'm thinking about, she is the bride, winner of her family. She makes a very nice living, but she cannot stand her job. And she's kind of slowly morphed into the business of, uh, the business of corporate coaching. And it is really about the bottom line. And when you're talking about 2, 2000% raise, I think you're probably also talking about up, leveling and raising your life by 2000% as well.

Speaker C: Exactly. Exactly. The initial name of the book was. Was, um, specific to compensation, but I brought into the term greatly, um, by. When I. When I started the podcast.

Speaker B: The most amazing podcast.

Speaker C: Thank you.

Speaker B: The, The.

Speaker C: The. The specific term it was originally meant for would have lasted maybe two or three episodes. I needed to broaden that. And, and we do everything.

Speaker B: Do it.

Speaker C: Yeah, we.

Speaker B: And.

Speaker C: And it could be in life too. You know, we have a financial focus, profess, um, growth, but. But it's also just leveling up, um, yourself with. With, you know, in life in general.

Speaker B: Doesn't just thinking about the bottom line and finances just get old after a while? I mean, okay, when you're at a certain place and you don't care about money anymore, but doesn't it just get old always thinking about, yes, you need shelter and Maslow's hierarchy of needs. You need shelter, you need safety, food, but at what point is it where you just shouldn't care?

Speaker C: Yeah, um, well, I'll answer that two ways, I guess. You know, I, I think, uh, I think I was kind of at that point when. When I. After I sold my company, I had an earn out with a private equity firm. And by the time that earn I was done, I was like, okay, I don't even m. Want to think about money anymore. I'm just ready to put this behind me. And luckily, I was in a position to, you know, enable me not to stress about it at least. And it wasn't until I started this podcast, Jules, that I, I became more intrigued, just. Just more globally with money. Because there's so many different ways to skin a cat and make money.

Speaker B: Look at how excited you look. You're like. Your eyes are popping out of your head.

Speaker C: You're like, seriously, I got into this venture capital stuff and these founders and

Speaker B: entrepreneurs, but it's venture capitalism. So, I mean, I know, but you probably have a better idea.

Speaker C: The easiest way to put it is like, Shark Tank, okay? Where people are.

Speaker B: Love myself some Shark Tank.

Speaker C: That's all right. That's right. So that's what I do for a living now. I retired. And by the way, as a venture capitalist, you don't necessarily make any money. We could call it a job, call it a criminal. Really, you're just. You're investing. So on a regular basis, all these entrepreneurs coming to me and founders and pitching Me ideas and you know, they're really just trying to raise money and uh, it's just, it's, it's um, it's exciting because you're finding things out that. Oh crap, I never thought of that idea. That's a pretty cool idea and oh, wait a minute. Okay. Like, like sports gambling is a big one right now, especially in Illinois. It's, you know, if you turn on the damn.

Speaker B: We're both from Illinois if you haven't noticed. Gotta get out of the state.

Speaker C: Well, I think there's about 20 states roughly right now, I think 25 or whatever. But call 2020 states right now that sports gambling is legalized there's 30 states that it's not. Now there's entrepreneurs though thinking that this is an immature space that's still going to be, that's going to be huge. Kind of like cannabis in years past where it used to be just California and Colorado and over time now it's Illinois.

Speaker B: Welcome um, cannabis family.

Speaker C: And as all these other states seeing the revenue that they're missing out on. Okay, that's starting to happen now with sports gambling where more and more spirits are coming on. So anyhow, you know, stuff that I normally wouldn't see on the surface or think about, all these entrepreneurs are coming out in the tech space with applications for sports gambling. I go whoa, that's a pretty crowded space. Yeah. But we're going to focus on, you know, Wisconsin where it's not legal yet. Uh, we're going to get players involved like in a free to play game. And then when it comes there, a big company like fanduel or Caesar's palace or whomever is going to come and buy us out and no one may invest, maybe I don't. But just hearing people's mindsets, you know what I mean? Like, like for me that's not. I never built a company to sell it one day I built a company to make money and how to help my clients. I got, I was fortunate. Private equity came in and bought us for, for a lot of money.

Speaker B: But what do you mean by private equity bought us?

Speaker C: So private equity firms will um, in my case it was called a private equity roll up approach where they were buying other. It was a big insurance company was buying smaller insurance companies up, enrolling them into their organization. You know that that's how it works. And they typically buy you for some kind of multiple um, of your revenue. So you have this, you have this huge payday. So like hello. Exactly. So that's kind of what happened. I Was like, I'm never selling my company. I'm handed off to my kids one day and whatever. And yeah, then private equity entered the insurance space and damn those kids.

Speaker B: They can figure it out on their own. Right?

Speaker C: Yeah, exactly. Sorry. Um, they basically bought us for like 12. It would have taken me 12 more years to make what I made in the one transaction. So I'm like, okay, well, I never had private equity not been involved. It never would have sold for that much. So I was very fortunate from that standpoint.

Speaker B: What is hitting a windfall like that do to you as you as a human being? Because I know, like, if someone senses that you're famous or you have a lot of money, you make a lot of friends that truly aren't real. Real friends.

Speaker C: Yeah.

Speaker B: Where you gain negative attention.

Speaker C: That definitely happening has happened. Um, you know, for, for me, I, I, when I built my company, there was a build. I, I owned it for almost 10 years. So there was a build where I was doing better and better each year financially. So I had kind of eased into it. It wasn't like I went from, you know, like rags to riches in one transaction. The biggest difference for me, though, was I was making that much money. And the reason private equity was, was buying us, me for that much was because I was making a lot of money. They would have done that if we weren't. So. So, you know, the biggest game changer for me with that event, if you want to call it that, was that I didn't have to work anymore. So I go from spending all this time. I was 37 years old, my rear off. It's old. I was 37. I was working my rear end off. It was, uh, 2015. And, um, you know, just, you know, then that, then that happened, and I didn't have to work anymore, which was, you know, crazy. Wait, is my math wrong? I hesitated. Wait, what was it? 2015, was that 37? Yeah. Yeah.

Speaker B: You're 44 now, right? Look at that research. Thanks, Google.

Speaker C: Uh, I'm actually, no, I'm not 44. I just turned 46 in December.

Speaker B: Oh, you're not that much younger than me.

Speaker C: Yeah, but I just turned 46, so. I see.

Speaker B: This is what happens when you ask for a tooth. 2000% raise. You have no idea how old you are.

Speaker C: Did I still on 2014? Maybe I did. Anyway, no, I sold on 2015.

Speaker B: The devil's in the details.

Speaker C: I'm 46 now, but it's December of 2022 right now. So anyway, I'm have to get a Calculator out. I'm confusing myself. But. But that was the biggest difference.

Speaker B: And you're a numbers person, right, too? Should it be?

Speaker C: I am. And if it wasn't going to be boring for your audience, I would like pause our interview right now and.

Speaker B: Oh, I'm an editor. He can pause it.

Speaker C: Um, I guess. I was 38. I was 38. So.

Speaker B: So now we know you can do this at 38 years old. But, uh, you know, I find it fascinating. You do this, you're calling your own shots, you start your own biz, and then you're kind of just. You know, I think what I really love is that you're calling your own shots. You, uh, are calling the 2000% raise, and. But now you could. You have even more control, so to speak, over your life. I mean, you can go to Mexico for a week. You can do a podcast, you can write a book.

Speaker C: Yeah.

Speaker B: I mean, what. What does the future hold for someone that is calling these shots and who's living life as an X ing it?

Speaker C: I, uh, you know, and by the way, my math was screwed up. I was 30.

Speaker B: Oh, Harry's going back, you guys. How old is he? He has no idea. This is the funny part.

Speaker C: I was supposed to do an employment contract. An employment contract for five years after I sold, and I only ended up doing it four and a half years. That's when the math was screwed up. The process started.

Speaker B: When I forgive you, we forgive you here at the meeting.

Speaker C: You're always gonna be like, this guy's full of. He doesn't even know what he sold this company.

Speaker B: But it's because you can just, like, live in your life so you don't think about these things.

Speaker C: Yeah. Um, but, you know, the biggest thing for me in that regard is, and it's something I'm still wrapping my head around, is this. You spend your whole life building, building, building, trying to, you know, like, make money. And I'm saving money, putting it away. I was never doing stupid when I was younger. Like, I live downtown Chicago, and I was like, you know, all the. All the cool kids are driving their, you know, Lamborghinis and buying boats. I never did any of that knowing. Knowing I was in financially way better position than a lot of people that were. And, um.

Speaker B: Um.

Speaker C: Because I was always trying to save. I was always trying to save. And then when I got to the point where I'm mad, you're now spending. Because I don't have any. I don't have any money coming in, so it's Right. So now it's like money going out instead of in. And it's, uh, you know, it's a paradigm shift.

Speaker B: It's so fascinating to me. And it's a lifestyle so. So many people are just driven to live by, but yet so many people are caught up in that cycle of the corporate handcuffs. So I love that. What would be the best tips that you could give somebody to kind of take that leap to start calling their shots, to ask for from themselves? Really? A, uh, 2000% raise?

Speaker C: Yeah. Well, I, I always recommend, and I know this is not realistic for everybody, or maybe people aren't going to be passionate about it as much, but I like to tell people to say, evaluate, uh, yourself within your industry and start a job within the industry or start a company within the industry that you're in or, or at least evaluate what your worth is to that organization. Okay. Some roles are a lot easier to figure this out if you're in, like, a production or sales rep role. Okay. Figure out how much of the company's resources you're using in that sales process. All right. Exactly. Well, again, and it's like, okay, how much money are you bringing in? Uh, depending on what you're selling, the math could get a little bit, you know, more. More complicated. But. But how much are you making? Is you have an account manager that's helping you? Do you have a manager that's actually active? How much would a office rent be? And then compare that number versus. Versus the money that you're actually bringing in, and, you know, that's what the company is making off of you and start looking at it, you know, through that, through that lens. Now, if you're, if you're, um, not passionate about an industry that you're in, um, you know, but you want to, you know, you want to be a business owner, find something that you're actually interested in and get a job in that industry before you turn around and start your company. The only exception to that would be is if you went to, like, a franchise model or something like that where, where they're going to train you and they're going to hold your hand. Um, but. But I tell people, though, like, you know, you don't, you know, if you have. If you've been, you know, you know, a pr. You've worked at a PR agency, you don't turn around, you know, start a nail salon or don't start a med spot.

Speaker B: Right.

Speaker C: You know, people come up with the idea that they could start a med spa because they go to med spas a lot.

Speaker B: I mean, yeah, they like Botox.

Speaker C: Exactly. Exactly.

Speaker B: So, no, that's fascinating. It's staying in your own lane, but by. But being creative as well and doing it the right way, finding those anchors, finding those mentors like John Sarasani.

Speaker C: Thank you.

Speaker B: He's amazing. And I think everybody out here needs to do a self evaluation, a self audit on their lives, their professional lives, and are they doing the thing that is going to feed them to their very last breath? And I cannot wait for your book to come out. 2000% raise. John Cerisani. And also you have to listen to his podcast. Everything is going to be in the show notes and we're going to finally figure out how old he is. But that is what I. That is what we're dying to know. How old is he? And still calculating it in his head. It. It's a pleasure. And you follow him on Instagram. He's got an amazing feed. He's inspirational, and he'll give you kind of that little push to think about things differently. So thank you so much, John, for being here. I'm a huge fan and you are always welcome here on the mediacasters. So I end every episode by asking every guest to say, let's kick it. Let's do it. Let's kick it, let's kick it. Creative Entrepreneur Podcast with your favorite entrepreneurs, Julie Loken, Lauren Erickson, and Dominic Damasky. Don't forget to follow us. Rate, review and subscribe to the Creative Entrepreneur Podcast. Until we meet again. Keep creating.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Pat McGovern - Bowery Capital - Where Vertical AI WinsCloud Returns · on Venture capital87 / 100
  • The Autonomous Digital Economy Is HereFinding Peak w/ Ryan Hanley · on Venture capital82 / 100
  • Quitting vs. Giving Up with Mike Evans, the Founder of GrubHubFounders Forward Podcast · on Venture capital82 / 100
  • The Truth About Bootstrapping an AI Startup with David Pourquery (#80)Exit Algorithms · on Venture capital81 / 100
  • The Mission Generation Wants Impact. Must They Choose Between Tech and Public Service? - Arun Gupta, CEO of NobleReach FoundationThe TechEd Podcast · on Venture capital81 / 100
  • Fund Administration: AI’s Growing Impact on Fund ServicesDeciphered: The Fintech Podcast · on Venture capital81 / 100

More from Creative Entrepreneur

All episodes →
  • Building a Magnetic Brand, Embracing Change & Owning Your Zone of Genius with Ramon Ray
  • Start A Podcast and Start A Movement with Julie Lokun
  • Content Creation and The Power of Building a Brand Like Gary Vee
  • Designing Spaces, Healing Stories: Mary Elisabeth Denmon on Transforming Homes, Overcoming Trauma & The Princess and the RV
  • What is Public Relations? And How Can You Be Your Own PR Pro! With Julie Lokun
Explore the best B2B Marketing podcasts →
All Creative Entrepreneur episodes →