Quick answer
Rob Miller is a Chicago-area serial entrepreneur and angel investor. He says he has founded eight companies, exited six and grown one to a billion-dollar valuation. He is CEO and co-founder of RegAssist, which builds custom AI answer engines, and co-founder of Manse, an AI house manager app that launched in beta in September 2026. On TikTok he shares startup advice, especially on pitching investors.
If you have a 15-minute meeting with an investor and plan to spend 14 of it on your product, Rob Miller has blunt advice: “you should just quit right now.”
Miller has heard a lot of pitches. He describes himself on @rob_miller_founder on TikTok as a multi-time founder and active angel investor, and in one video he puts the record at eight companies founded and six exited, one of which reached a billion-dollar valuation. His point is not that the product doesn’t matter. It is that investors are buying proof that someone will pay.
Key takeaways
- Miller says he has founded eight companies and exited six, one of which reached a billion-dollar valuation.
- He is CEO and co-founder of RegAssist, a Chicago AI company that builds answer engines for regulated industries such as aviation and college sports.
- In September 2026 he and real estate agent Dawn McKenna launched Manse, an AI house manager app, in beta.
- His pitch advice: lead with proof of demand, not the solution, because building has never been easier.
- His most-watched video, with about 123,000 views, argues that real-world AI adoption is far slower than the headlines suggest.
Who is Rob Miller?
Miller is a serial entrepreneur and angel investor based in the Chicago area. RegAssist‘s founder page describes him as a seasoned entrepreneur with multiple exits, and says the company grew out of a college pitch competition, where he teamed up with student founders Luca Foglio and Emil Barr instead of competing with them. He now serves as RegAssist’s CEO.
His story runs through the companies he has started. In one video he recalls that at his first startup, the team did not have the cash to build what customers wanted, so they asked for deposits on equipment that did not exist yet. “Three customers said yes,” he says. “That’s 3 million bucks.” That became the company’s first capital.
What is Manse?
Manse is an AI house manager app. Homeowners add their address, photograph the serial tags on their appliances and upload documents such as an inspection report, warranties and insurance policies. Manse identifies the exact appliance model, pulls its manual, warranty status and recall history, and answers questions about that specific home.
According to its launch announcement, Manse is a joint venture between RegAssist and the Dawn McKenna Group, a luxury real estate team, and it began with a conversation between Miller and McKenna, two friends from north Chicago. It launched in beta on September 17, 2026, rolling out first to the group’s clients, at $288 a year or $29 a month on a 12-month term.
“Manse works from your home’s own records,” Miller said in the announcement, “so the answer is for your exact house, and it comes with the next step, not just the fact.”
What does Rob Miller look for in a pitch?
Miller’s most-viewed pitch video is built on one idea: the problem matters more than the solution. With no-code tools and AI builders, he argues, almost anything is feasible now, so the real questions are whether people want it and whether the business can make money. He points founders to author Ash Maurya and to three tests: desirability, viability and feasibility.
Startup founders: stop wasting your 15-minute investor pitch
In a more recent video on raising a first round, he boils a fundable pitch down to three things:
- A sharp team, with one person who is technical and one who can sell.
- A market big enough that the math works.
- Proof that real customers will pay real money. Contracts and letters of intent beat a deck and a dream.
Of the three, he says, proof of payment matters most.
How did he keep a company alive with zero revenue?
During the pandemic, Miller says, one of his companies was shut down for almost a year. Revenue went to zero, but the expenses did not move. In a video about that year, he explains that he did his homework first: what was the business worth to the people he owed?
An empty building was a landlord’s nightmare, so he asked his landlord for help in exchange for staying a long-term tenant. With suppliers, he asked for longer payment terms instead of lower prices. That, he says, let the company keep everyone on salary until it came out the other side. His takeaway: “your leverage is knowing what the other side fears losing.”
What else does he talk about?
Miller’s channel mixes startup lessons with the rest of his life. He is a pilot and has posted from TAC Aero, a tailwheel flight school in Texas, about how casual conversations at the airfield turned into new ideas for Manse. He calls the habit “talking your book,” a phrase he picked up from a friend in private equity.
He also champions military veterans as founders. Many of his companies were founded with veterans as key leaders, he says, and the military rewards exactly what startups need: small teams, hard missions and limited resources. And as someone building AI, he is candid that adoption is slow, which means AI founders need more runway than they might expect.
Frequently asked questions
Who is Rob Miller?
Rob Miller is a Chicago-area serial entrepreneur and angel investor. He is CEO and co-founder of RegAssist and co-founder of Manse, an AI house manager app. He says he has founded eight companies and exited six.
What is Manse?
Manse is an AI house manager app from RegAssist and the Dawn McKenna Group. It reads a home’s own records, such as appliance serial tags, warranties, inspection reports and insurance policies, to answer questions about that specific house. It launched in beta in September 2026.
What is RegAssist?
RegAssist is a Chicago AI company that builds custom answer engines trained on an organization’s own information, with work in regulated fields such as aviation and college sports compliance. Rob Miller is its CEO.
What does Rob Miller say investors want to see?
He says investors want a team with technical and sales skills, a large enough market, and above all proof that customers will pay, such as contracts or letters of intent.
Where can I follow Rob Miller?
He posts startup and homeownership advice on TikTok at @rob_miller_founder.
Try Manse
Learn more about Manse at mymanse.ai, and follow Rob Miller’s startup advice on @rob_miller_founder on TikTok.
This profile is based on Rob Miller’s public videos, Manse’s published launch announcement and RegAssist’s website. Booked Impact did not interview him, and he did not review this article before publication. Career figures are as stated by Miller.
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