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Connor Tomkies Considered Retirement at 30, Instead He Launched an Investment Firm

With Operator Equity—a cross between a private equity firm and a family office—Tomkies is investing in post-exit founders.
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Connor Tomkies

Connor Tomkies had a busy decade in his 20s. In 2014, the UT Austin grad co-founded DelegateIt, an omni-channel back-end software for Airbnb and HomeAway properties. At the same time, he launched EmbarkVet, a dog genetics company that garnered an investment from SoftBank. Soon after, Tomkies launched outsourcing company SupportNinja in 2016—as CEO, it was the startup he spent the most hands-on time with. 

In 2021, he relocated the company’s headquarters to Deep Ellum and, a year later, sold the business to BV Investment Partners for $40 million. Tomkies grew SupportNinja’s employee base to nearly 1,000. 

After stepping down from the CEO role post-integration, the soon-to-be 30-year-old started deciphering what he wanted to do next. “It really opened the door to everything that I was excited and passionate about,” he says. “But I did try to retire for a week, and it didn’t work out.”

Instead of becoming the youngest person to ever live in a Margaritaville retirement community, Tomkies opted to launch an investment fund in July of 2023 that is somewhere at the crossroads of a family office and a private equity firm. He calls it “almost like a mini Berkshire Hathaway.”

 It’s hard to understand, but necessary, that we entrepreneurs are more robust as human beings than what our job is. 

Connor Tomkies

Dubbed Operator Equity, his fund—which at this point has only deployed cash from Tomkies’ personal pockets—invests in cash-flowing businesses, usually between $5 million to $25 million in revenue. Right now, he has a team of six full-time employees, along with an army of contractors. What separates it from a private equity firm, though? “The LPs are different. The horizon is different. So, there’s not a three-to-five-year horizon—the expectation with the LP is that it takes however long it takes; it is up to the founder how long they want to hold on,” Tomkies says. “If CEOs sell their company to Operator Equity, they can be involved in other investments. And that’s good for their growth trajectory. Arguably, the next stage of growth, beyond entrepreneurism, for a serial entrepreneur or a post-exit entrepreneur, is venture. 

“What I like about the model I’ve built is that the LPs are post-exit founders,” Tomkies continues. After all, he was just recently part of that demographic. “A lot of private equity firms say things like, ‘We have this connection with our portfolio, and we can cross-sell into our portfolio and share best practices.’ But, in reality, there are a lot of islands.

“The post-exit founder has time. We have money. We have resources. We have know-how. And we’re antsy. So, my goal was to connect all the local post-exit founders and get us into a group.” So, not only is Tomkies investing in these founders’ second, third, or fourth acts, but he has also spearheaded the creation of a DFW community group for the post-exit founders beneath the umbrella of Entrepreneur Cooperative, which has more than 100 members. As one of his investments, the company is a membership-based community that includes seasoned and emerging business leaders in this in-between stage of their careers. 

“Almost all post-exit founders have an identity crisis,” he says. “Normally, we introduce ourselves as the CEO or founder of X, Y, or Z. But once we exit our company, we need to figure out if we want to introduce ourselves as a father, a pickleball fan, or whatever. So, it’s hard to understand, but necessary, that we entrepreneurs are more robust as human beings than what our job is. So, this cooperative helps with the connection piece and provides loads of value for those involved.” 

Operator Equity has invested in the marketing platform Incendium Strategies, Entrepreneur Cooperative, Taylor Robinson Music (which was featured on Shark Tank), and CXC Solutions. Some stakes are majority, some are minority—ideally, Tomkies aims to acquire between 40 and 70 percent of a company. Some investments are cash, and some are leveraged. “The total revenue being generated of the companies we’ve invested in is just north of $100 million,” he says. 

Tomkies makes it a point to not only invest in the companies, but get hands-on. “I can either acquire a company that I’m interested in and then I can add stuff on top of it, or I can launch something and work with the other entrepreneurs to build something special. So I’ve combined both of those elements,” he says. 

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Similarly to his involvement with Entrepreneur Cooperative, alongside Incendium Strategies and California-based entrepreneur Andrew Warner, Tomkies has launched his podcast “Made It with Connor Tomkies.” Early podcast guests include Alex Lieberman, who co-founded the Morning Brew newsletter, which he sold for $75 million at a valuation of more than $440 million, and Jeremy Parker, who scaled Swag.com to $40 million in sales before Custom Ink acquired it. Originally named “My Second Million,” the podcast covers entrepreneurs who have built, scaled, and sold their companies and are now on to a new venture. 

Five years down the road, Tomkies sees Operator Equity as a “massive network of post-exit founders and pre-exit founders working together in different countries around the world, tied together by a single fund investing and reinvesting. “And I think it will be a pretty big economic force; I can see it being a big ecosystem,” he says. 

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Ben Swanger

Ben Swanger

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Ben Swanger is the managing editor for D CEO, the business title for D Magazine. Ben manages the Dallas 500, monthly…
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