Michael Sirpilla and the art of staying after the sale

Selling your company is supposed to be the ending. There is a signature, a transfer of money, perhaps an unusually good dinner. Michael Sirpilla has built much of his pitch around what happens on Monday morning. He would rather the founder came back to work.

At Society Brands, the company he co-founded in 2020, an entrepreneur can receive cash for a business, retain an interest in its future through equity in the parent company, and continue as a brand president. Sirpilla is selling a peculiar combination: the relief of a transaction and the unfinished business of building something. Retirement is optional. There is still inventory to order.

That proposition gives his story its central tension. He wants the advantages of size without losing the knowledge accumulated by someone who has personally answered the customer emails. As CEO, his job is to make those two things coexist. A founder may want a cheque and colleagues. The acquiring company must then become worth having as a colleague.

A family business, then a different instrument

Sirpilla was born and raised in Canton, Ohio, in a family for whom retail was an actual occupation, rather than a case study. His grandfather John B. Sirpilla and great-uncle Art developed a gas station that rented campers into a recreational-vehicle supercenter. The business eventually became part of Camping World. Expansion, in this family, had a local address.

Michael and his younger brother Justin would later return to that geography with a different sort of retail business. When they introduced Society Brands in 2022, Michael credited the foundation their grandfather had built. Their early offices occupied buildings on Whipple Avenue connected to another family business, Laura of Pembroke. The internet had made the merchandise portable; the family connections remained close to home.

His own route took a detour through music production. He studied it before turning toward business as a career. A financial-services wholesale agency followed, growing into a multimillion-dollar operation with a team of 40. His earlier company biography describes him training and mentoring hundreds of sales professionals. Before he was asking entrepreneurs to join a group, he had spent years assembling one.

There was a football captaincy at St. Thomas Aquinas High School, too, and a continuing interest in guitar and piano. These are modest biographical details, but useful ones. A person who has recruited salespeople, captained a team and played music has encountered several ways of discovering that individual enthusiasm still needs coordination. The later business would give him plenty of opportunity to practise.

The cheque came with company

Society Brands launched in October 2020. Michael had already been talking with Amazon retailers and considering acquisitions when he brought the idea to Justin. His brother offered experience from a company that had completed 26 deals in two and a half years. Alongside co-founder Shawn Dougherty, they assembled a business intended to buy and develop online consumer brands.

On March 9, 2022, Society Brands announced $204 million in institutional capital led by i80 Group. The sum combined debt and equity. It was financing for the company’s acquisition plans, rather than a personal fortune or a valuation. The distinction matters whenever a funding headline acquires a life of its own.

Sirpilla had initially been looking for at least $100 million. Working with merchant bank SenaHill Partners, the company spoke with multiple potential backers. i80 offered roughly twice the original target. Yet the detail Sirpilla remembered was the first video call, before the conversation had become an exercise in comparing numbers.

“We were on a Zoom and it just felt right,” he said. He described calling the investment banker afterward because the people seemed like a fit. He also valued their patience while other conversations continued. For someone arranging a large pool of acquisition money, his account spent a striking amount of time on how it felt to speak to the people providing it.

A new title for the person who knew everything

By September 2022, the portfolio had added Yankee Toy Box, Barnesmith and Capsule Supplies. All three acquisitions were announced with founders staying involved. The products varied; continuity at the top was part of the offer. Barnesmith brought collegiate apparel, while Yankee Toy Box brought licensed children’s merchandise. Nobody could accuse the shopping list of lacking range.

In his public explanation of the model, Sirpilla gives the retained founder responsibility for the brand’s profit and loss. Society supplies shared capabilities such as marketing, supply-chain work, inventory management and new-product support. The founder contributes the accumulated understanding of the business: which customers care, what they buy, and what experience has taught the operator to watch.

There is a financial reason to remain interested as well. Equity rolled into the parent company ties part of a seller’s future return to a wider collection of businesses. A later sale could create another payout. That is an opportunity embedded in the structure, dependent on future performance and a future transaction.

In 2022, Sirpilla put his view of expansion plainly: “If you’re trying to grow a business to exponential levels, you can’t just do it by yourself.” The statement sounds uncomplicated until the collaborators have sold companies to one another. Then roles, budgets and authority all need rather more precision than a friendly introduction.

The work between the acquisitions

The first year of buying also involved building the machinery to support what had been bought. In its February 2023 update, Society reported six acquisitions during 2022, a workforce of 65 employees and contractors, and more than $1.5 million in annualized cost savings from combining operations. Those were company-reported measures of the early integration effort.

Its proprietary technology platform, EVO, belonged to the same effort. Buying several brands creates a collection of businesses; operating them together requires information to move between people who previously worked separately. Product development, finance and supply planning are less photogenic than a signed agreement, but the agreement depends on them afterward.

Sirpilla later discussed quarterly gatherings where founders exchange ideas. The practical appeal is straightforward. Someone who has solved a problem in one brand may save another operator the expense of learning it from scratch. The acquiring company has to arrange enough useful cooperation to justify its place in the room, while leaving people enough responsibility to keep caring about the outcome.

By July 2024, Society’s annual revenue had passed $100 million. Sirpilla also discussed a portfolio of 12 acquired companies and an increasing emphasis on brands selling directly through their own websites. The original Amazon acquisition pitch was becoming a broader consumer-products operation.

“We were on a Zoom and it just felt right.”

Michael Sirpilla, recalling the first i80 Group call

When partnership becomes a dispute

The arrangement has also been contested. Trina Felber, founder of Primal Life Organics, sued Society Brands and others, including Michael and Justin Sirpilla, after a December 2023 transaction. Her allegations concerned representations made during the deal, contractual obligations and the use of her identity after her employment ended.

The defendants disputed the claims and argued that the signed agreements gave them management authority and grounds to terminate her. A trial court dismissed the case in November 2024. On August 4, 2025, Ohio’s Fifth District Court of Appeals reversed that dismissal and returned the case for further proceedings. The ruling addressed whether the claims could proceed; it did not determine that the allegations were true.

For a business whose proposition depends on founders staying, the dispute exposes a consequential question: what does staying actually permit someone to decide? Collaboration has to survive the language of employment agreements and ownership rights. The difficulty belongs inside Sirpilla’s story because the continued relationship is central to the business he has chosen to build.

Canton, with a wider audience

In July 2025, Society announced its first athlete partnership with PGA Tour golfer Justin Lower, another Canton native. The arrangement covered promotion during 2025 and 2026, with Society and portfolio-brand logos appearing on Lower’s hat. Sirpilla connected the deal to a wider intention to work with athletes and celebrities.

The choice joined a personal interest in golf to an identifiable business aim: getting brands in front of a national audience. The photograph of Sirpilla and Lower sharing a golf cart makes the hometown connection unusually easy to see. For once, the meeting room had a steering wheel.

September brought a partnership with cosmetics company Crunchi. Founders Kelly Kreusler and Melanie Petschke remained involved in leading the brand. Society reported more than $160 million in annual revenue at that point, with more than 70 percent coming through direct-to-consumer channels. Those figures describe the company in that announcement, rather than a running score updated automatically with every new deal.

In December 2025, Society partnered with Caravan, a brand studio backed by Creative Artists Agency. The first collaboration centred on home-products brand Cleanomic, with plans to connect it to talent, creative partners and retail relationships. Sirpilla’s acquisition business was now arranging access to audiences as well as access to capital.

His name also appears on the Canton Regional Chamber of Commerce’s 2026 board roster. The national marketing ambitions have not removed the local commitments. That combination runs through the career: a family history in Northeast Ohio, a business built there, and repeated attempts to make the circle of useful relationships larger.

The person who comes back on Monday

Away from the transaction announcements, Sirpilla calls himself an extrovert. His stated motto is “Mercy over judgment.” Asked to cast a film of his life, he chose Ben Affleck and the title Underrated. An acquisition executive with an imagined biopic has at least considered the casting budget.

The ambition he describes professionally is to build a multibillion-dollar consumer-products company. The route he has chosen depends on persuading other ambitious people to join him after they have reached a moment when they could leave. That makes the days following a sale as revealing as the day it closes.

Sirpilla has obtained capital, bought businesses and broadened the audience for their products. The continuing test is more intimate: whether the entrepreneur who knows a brand best finds good reasons to keep contributing. Monday morning keeps arriving. There is always another customer, another order, and another conversation about who is going to do the work.