Founder Guidance

Illustration: Morning Brew Inc., Photo: Jamie Siminoff

For some founders, the goal is simple: Build something great, sell it for a lot of money and exit on top.

Ring founder Jamie Siminoff did that. But his experience after the sale offers a different lesson: Sometimes the biggest payoff comes from thinking beyond the deal itself.

After seven years of building Ring, Siminoff sold the video doorbell company to Amazon in 2018. Rather than treating the acquisition as the end of his involvement with Ring, he stayed on at Amazon, eventually stepped away for a few years and returned again in 2025.

Today, Siminoff, serves as Amazon’s vice president of product and said his return allowed him to “go back to my playground and build stuff.”

His path offers an unusual look at life after an exit—and the trade-offs that come with going from being the person calling the shots to working inside a much larger company.

Exiting doesn’t always mean leaving

Instead of viewing the sale as a handoff, Siminoff saw the Amazon acquisition as a continuation of his trajectory with Ring.

“I really wanted to continue running and building the business when I sold it, and part of why I sold to Amazon is I felt that they would allow me to,” he told Founder Brew. “I definitely was not done with it yet.”

He considers his “first tour of duty” with Amazon as a success. “I stayed for five years,” he said. “I built it, almost 10x-ed the business between when I sold it to Amazon until I left. I got it profitable.”

That success came at a cost. “I also burnt myself out. I had been doing it for at that point like seven years myself, as a private company, and then five years at Amazon,” he said. “I needed to take a step back and just take a few years off.”

About two years after he stepped away, though, he felt ready to return, especially as new advances in technology seemed poised to create new opportunities.

“One of the big things that brought me back was AI,” he told Founder Brew. “I call myself the chief inventor. I really like to invent things and build stuff, and AI really unlocked our vision of making neighborhoods safer. It unlocked—literally—a whole new world of inventions and things that we could do with what we built.”

For Siminoff, the difference between leading Ring as its founder and working for Ring under Amazon’s ownership was less than it might seem to an outside observer. While running an independent company, he always had to deal with outside investors and the pressure of keeping the Ring running. “I certainly was able to make more decisions. That said, the flip side of that is I had to raise money,” he said.

And Amazon’s resources, he said, didn’t hurt. “It might be, for an inventor, more fun to be in a place like Amazon than to be an independent company,” he said. “If I come up with something, I can fund it. I can get it out there.”

Read more about Jamie Siminoff’s post-exit life at Amazon.—JH

      

Sponsored By Capital One Business

Adele Gambardella managed corporate disasters before they hit the headlines. Chip Massey negotiated hostage situations as an FBI agent. Neither expected to start a company together. But they discovered negotiators and crisis pros run on the same playbook—different rooms, same pressure. That became The Convincing Company.

The real proof of concept wasn’t the UN keynote or the 200+ TV hits. It was eight years ago, when they booked an NYC workshop venue on a Capital One Business card before a single ticket sold. That night sold out.

Now they’ve built The Convincing Lab: a quiz that shows how you actually perform under pressure, based on real crisis methodology, not theory. Take the quiz to see how you’d hold up.

Adele and Chip started their business at a dinner party. Capital One Business can help wherever you are in your journey.

Founder Guidance

Illustration: Morning Brew Inc., Photos: Labucq

Lauren Bucquet spent nearly a decade learning how to build footwear inside an established fashion company. Then she decided to see what she could build without one.

As design director at rag & bone, Bucquet worked with factory owners and patternmakers to develop footwear and accessories for the brand. But after 10 years, she was ready to leave institutional fashion behind—and take the expertise she had developed there with her.

Bucquet joined rag & bone when it had just four employees and watched it grow to roughly 350 by the time she left. That early experience was formative: There was no product development team, so designers worked directly with factories and took on responsibilities well beyond design.

As the company grew, she missed that scrappy environment and the founder mindset that came with it. But she wasn’t leaving with a business plan in hand.

“I didn’t have the idea to immediately start my brand,” Bucquet said. Instead, she moved from New York to Los Angeles and took on freelance consulting work, a reset that gave her room to think about what she would do differently if she built a brand of her own.

In October 2018, Bucquet launched direct-to-consumer contemporary women’s footwear brand Labucq, a portmanteau of her first and last names. Starting the company wasn’t simply about putting her own name on a shoe—it meant figuring out how to make decisions without the structure she’d spent her career working within.

Stepping out

When Bucquet entered the footwear market, she knew she needed to find an opening where her experience could give her an edge. As direct-to-consumer brands gained traction, she saw an opportunity to bring a design perspective and level of craftsmanship she had trouble finding elsewhere.

“I wasn’t seeing anything with the design perspective that I could bring to the table,” Bucquet said.

At the same time she was also paying attention to the risks built into the traditional fashion business—watching department stores struggle financially and hearing stories about brands waiting to be paid. For Bucquet, that made independence feel less like a gamble and more like a way to reduce her exposure to a system she no longer trusted.

“If we could figure out how to market online and sell directly ourselves, why not operate independently and not be relying on orders and payments from outside vendors?” she said.

Read more about Lauren Bucquet’s decision to start her own company.—JH

      

Tips and tricks for negotiating with AI vendors (IT Brew)

AI vendors “range in where they’re adding value” across the tech stack or supply chain, executive tells IT Brew.

Department of Labor changes disability hiring rules for federal contractors (HR Brew)

The government is ending a 7% representation goal and will no longer collect disabled worker data, concerning advocates.

Communicating value is “the biggest piece” in divestitures (CFO Brew)

Finastra’s CFO Carissa Kell details her role in a series of business unit and product sales.

Sponsored By Capital One Business

Workshop on a rewards card. Adele Gambardella and Chip Massey, crisis PR pro and hostage negotiator, respectively, built The Convincing Company from a dinner party conversation. They used their Capital One Business card to book their first NYC workshop. Now they guide heads of state on dealing with high pressure. No journey is too big or too small.

Stat: $200,000. That’s the amount Colorado cafe chain Convict Coffee says it has raised for prisoners and formerly incarcerated people. The chain’s founder Dan Klehm first learned how to make “prison coffee” while serving time, and has been working in the restaurant business since he was last in prison 30 years ago. (Denverite)

Quote: “Founders who are exiting a business that was their baby need to remember that you have no control over any part of the business once you accept the money and exit. No matter what you are promised for the company’s future throughout negotiations, the new owner’s vision may change, and you have to be prepared for that.”—Marsha Martin, founder of beauty products company Onyx Brands, on the process of selling her company to private equity in 2021 (Arkansas Business)

Read: Corporate layoffs and a tough job market are making it more difficult for workers to grow their careers. For many, the solution is to take the plunge and start their own companies. Perhaps you’re one of them? (the New York Times)

^{*A message from our sponsor.}