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How to Sell Your Company in 9 Months with Connor Tomkies

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Connor Tomkies' Journey from Bootstrapping to Acquisition

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This week, I talk with Connor Tomkies, a serial entrepreneur, investor, and post-exit founder of Support Ninja. Connor took his experience from working at a dog genetics startup to develop Support Ninja which he then scaled )via bootstrapping) into a middle eight-figure success story, managing thousands of employees worldwide.
He shares insights on acquisitions that could save you millions, and more on his new ventures, Operator Equity and Entrepreneur Cooperative, to support founders.

What you can expect:


    • 00:37 Dog genetics and the birth of Support Ninja
    • 02:54 Bootstrapping vs. raising venture capital
    • 05:30 Lessons from selling to private equity
    • 10:14 Why EOS is a game-changer for scaling companies
    • 18:34 Operator Equity’s focus on SaaS and ecosystem synergy
    • 27:00 Common founder mistakes and the value of recurring revenue
    • 30:45 The rise of moonshots and the future of venture capital

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ABOUT CONOR TOMKIES

Conor Tomkies is a serial entrepreneur, investor, and post-exit founder with a passion for creating scalable businesses and empowering other entrepreneurs. He founded Support Ninja, a bootstrapped outsourcing company that scaled into a middle eight-figure success story and sold it to private equity. Now leading Operator Equity, Conor focuses on acquiring and scaling SaaS businesses using the Entrepreneurial Operating System (EOS), helping founders navigate successful exits with a streamlined 45-day process that prioritizes simplicity and a human touch.

Conor is also the co-founder of Entrepreneur Cooperative (ECo) and host of the Made It Podcast. Through ECo, he has built a community where seasoned founders share experiences, collaborate, and gain insider strategies for navigating business sales and life beyond the exit. It’s the network every entrepreneur wishes they had when starting out, focused on meaningful growth, impactful exits, and supporting the next generation of founders.

Connect with Conor:

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How to Sell Your Company in 9 Months with Connor Tomkies

Published: · https://blog.thunder.vc/connor-tomkies · Thunder Podcast

Watch the video: YouTube Link

Episode Summary

Founder and operator Connor Tomkies breaks down how to run a tight M&A process in ~9 months—from picking a banker and building a buyer list to protecting your price and controlling legal costs.

Post‑exit, Connor explains Operator Equity, a holdco that buys and operates recurring‑revenue software companies, and how the EOS operating system creates accountability and shared cadence across the portfolio.

You’ll learn trade‑offs between boutique vs. big‑name bankers, typical ownership stakes (40–80%), alternatives to venture for founder liquidity, and practical tactics like SIM/NDA discipline and legal‑fee tracking.

Full Transcript

Connor Tomkies: We can if you want to let me know

Jason Kirby: Nah, it's fine. They do a pretty good job of chopping it bac... bringing it back to life. I've made that mistake more times.

Connor Tomkies: yeah, Jason, good to hear you. Good to have you with us.

Jason Kirby: So basically what you told me is you ran your own banking pr...s, they see your SIM or your confidential information random.

Jason Kirby: I guess how long did it take from the point of setting that ...rom the point you set it up to the point you close the deal.

Connor Tomkies: Too many questions. I think that if you run a tight process, nin...nce. Nine months is roughly the timeframe. And then I think from

Jason Kirby: And we ended up going with a small boutique firm because I liked...s. So I actually went with the firm that promised less in a way.

Jason Kirby: I see that happen with lot of bankers. kind of put a carrot out ... the price. And I see that often with bankers just promising the

Jason Kirby: Big carrot, they get you under contract and then it's like, well...ther. So, you know, small boutique firms sound like they did it.

Connor Tomkies: Yeah.

Connor Tomkies: At the end of the day, you're actually working a lot with the as...you're talking to is not always the person running your process.

Jason Kirby: rby (04:26.224) Exactly. you might be sold by the sizzle of one partner or someo...ss or was it a cohesive effort? What was that relationship like?

Connor Tomkies: It was cohesive. So we had a potential list of buyers that we we...ything that you do above this will give you a higher percentage.

Connor Tomkies: on that deal and anyone you bring to us that we haven't already ...ed up with going with one of the people that they brought to us.

Jason Kirby: No, it's awesome. it sounds like you ran an efficient process. S...d, what corners should they be looking around in the &A process?

Connor Tomkies: Yeah.

Connor Tomkies: There's a lot of little, sticking points, right? Like, making su...s make sure that you get your price up. One of the kind of like,

Connor Tomkies: You sell the company, you it a couple of years ago. What have yo...w and kind of what has guided you to the work that you do today?

Connor Tomkies: After selling the company, we sold to a private equity firm, whi... company called operator equity, which is essentially a hold co.

Connor Tomkies: where we start buying other companies, teaming up with other ent.... And so I've been working on that for the past year and a half.

Connor Tomkies: we also did something called the entrepreneur cooperative, which...an pull out that will save you a lot of heartache down the road.

Jason Kirby: And so going back to the entrepreneur collective, think that's the kind of PoltCo, correct?

Connor Tomkies: Entrepreneur Cooperative is the kind of like the community with the business edu

Connor Tomkies: cation piece and then Operator Equity is the hold to go.

Jason Kirby: I'm sorry, operator equity, So operator equity, what type of tra...ave prepared you for being on the other side of the transaction?

Connor Tomkies: I think every hold co has its own thesis. And what I've seen, wh...riod of time in the form of like decades instead of a few years.

Connor Tomkies: then this can be a more favorable structure. And all hold co's h...o that's the underlying thesis of essentially operator equity is

Connor Tomkies: They are all operating on the same base layer, the same operating system.

Jason Kirby: Okay, so this is is fascinating. I've been familiar with EOS and...ttle bit of context of what EOS is and kind of what it provides.

Connor Tomkies: ...

Connor Tomkies: And when you're buying these companies, you looking, have any of...pital history of some of these companies that you're looking at?

Connor Tomkies: All of them except for one, I think as bootstrapped and it reall... back and there's a spot open on their cap table or they're not.

Connor Tomkies: actively working in the business each day. And so I work with a ...ally get their, their earn out or, or their chips off the table.

Jason Kirby: So it sounds like you some flexibility in terms of what position...e cases. It's you're flexible. Is it majority often or minority?

Connor Tomkies: It to be a meaningful stake. So normally it's between 40 to 80%....can I give them the resources to, hit that next stage of growth?

Jason Kirby: Yeah, it's, it's, it's fun hearing this just because I deal with...th for something like you where it's like, well, what about this

Jason Kirby: other option of take some chips off the table? You know, be pro...re Kool-Aid for, for so long that they don't realize like, wait,

Jason Kirby: I get a multimillion dollar paycheck. today? It's like, and I still get that side.

Connor Tomkies: Yeah, it can be really nice. Distributions are a great way to be...ing capital and doing pitches for a bunch of different contests.

Jason Kirby: Who would thought?

Connor Tomkies: I was pitching three or four times a week that the company wasn'... hopefully this will kind of help highlight some of those paths.

Jason Kirby: You know, you just gave me PTSD. I did the exact same thing. fir...e realized, this is probably only a $10 million a year business.

Jason Kirby: ...

Jason Kirby: And so venture is prioritizing like next frontier, you know, and...n big moon shots. And so if you don't have that narrative, yeah.

Connor Tomkies: I'm seeing a lot more hardware, like software combined with hard...hat inside our cities have been raising a decent amount of cash.

Jason Kirby: Yeah. Industrial, defense tech, robotics, AI, things that at lea...unds like A16Z, think General Catalyst and a couple other big...

Connor Tomkies: Yeah.

Jason Kirby: funds have raised these huge early stage funds and they're just ...u're on the path to the moon? I guess we have the moon to Mars n

Jason Kirby: ow. It seems to be the narrative. It's like how quickly are you ... that path and what can you demonstrate or at least is the idea.

Jason Kirby: believable to be a part of those markets and be a part of those ...ising money than a SaaS business doing a million dollars a year.

Connor Tomkies: I almost feel like there's a limit to how fast the businesses ca...ead as a CEO to be able to do that through your growth plan. So.

Connor Tomkies: I'm a little curious with some of these companies that are raisi...ey take that check and actually turn it into a tangible product?

Jason Kirby: I think you brought up a good point earlier when you're kind of ...ne as it sounds to you and I that prefer operational efficiency.

Connor Tomkies: Can't it, please? Yeah.

Jason Kirby: ... Yeah, so it's entrepreneurcooperative.com and then operatorequit... I'm around guys and if you guys have any questions, me a shout.

Jason Kirby: Should they try to sell their company to you? Should they try to raise money for me? Coming for help?

Connor Tomkies: If you're selling a company operator equity, if you're trying to...ut entrepreneurcooperative.com. That's the right place for that.

Jason Kirby: Awesome. Connor, I really enjoyed this conversation. Really appr...te you being on the show and look forward to get this out to our

Connor Tomkies: That sounds good, Jason. Have a good one, guys. Bye.

FAQ

How long does a tight M&A process take?

About nine months from kickoff to close when executed with a disciplined buyer list, NDA and SIM control, and weekly cadence.

Should I hire a boutique banker or a big-name firm?

Boutiques can be better when the partner pitching also runs the process and sets realistic expectations instead of overpromising.

What is Operator Equity?

A holding company acquiring and operating recurring‑revenue software businesses with a shared EOS operating system.

What stake sizes are typical?

Meaningful stakes from 40–80%, tailored to founder goals and growth plans.

How do I avoid legal fee blowouts?

Track work via a simple spreadsheet, set budgets, escrow funds if needed, and approve scope changes in advance.

Do these companies raise venture capital?

Most are bootstrapped; alternatives include minority sales, distributions, and partial liquidity alongside growth capital.