Joe Zuk is an Operating Partner at Altamont Capital Partners and a strategic board advisor to InsurTech startups, bringing over 22 years of experience in helping founders navigate capital decisions. Peter Tilbrook is the Founder of Loro and host of "Age of the MGA" podcast, building his first venture in the specialty insurance market. Omer Rimoch scaled PayEm from 2 to 45 people and raised $47M and is now building Advance and coming from the FinTech space into insurance where network access was critical.
In this episode of FounderLM, Marissa Buckley brings together Joe Zuk, Peter Tilbrook, and Omer Rimoch to tackle a critical question that follows directly from Episode 5: How do you actually assess whether an investor can execute, not just promise support? Joe provides great advice—ask for receipts. Peter explains why insurance is different from other verticals and how quickly you can tell if an investor knows your space. Omer reveals the non-negotiable step every founder should take before signing a term sheet. This is execution over capital in practice.
This is episode 6 in a series of short conversations with 6 different founders and leaders sharing advice and real lessons learned while raising capital. You’ll get to know:
Grace Hanson, former founder of Seagull Cognition, now Founder of Elysian
Omer Rimoch, CEO and Co-Founder of Advance
Joanne Artesani, former AIG/Hippo, now Founder & CEO of Sproutr
Jamie Cuffe, ex-Sequoia data scientist and serial founder, now building Pace
Patrick Girouard, Founder of District Cover
Peter Tilbrook, Founder at Loro and host of “Age of the MGA” podcast
Ask for receipts—talk to their portfolio founders. Joe’s advice: ask to speak with CEOs of their current or prior portfolio companies. Get tactical examples of where they’ve brought in talent, leveraged their network to open doors, or provided operational expertise. Don’t just accept promises. You need to seek real evidence.
Omer was clear that getting founder feedback on investors is literally the best feedback you should pursue. If you have a term sheet or several term sheets, the answer is in their portfolio founders. That’s where the truth lives.
Watch how they respond to your questions. Joe shared a story of a founder who asked an investor what they could do to support him and what they knew about his business. The investor didn’t know much beyond the founder’s website. When the founder pointed out the investor’s website was blank, the investor said “we just like to run under the radar.” That’s a giant red flag. If an investor can’t demonstrate understanding or provide specifics, they’re probably not the right partner.
In specialized spaces like insurance, expertise becomes apparent quickly. Peter emphasizes that insurance is a massive spectrum with many different elements. If you’re in a niche like specialty insurance, an investor’s area of expertise becomes apparent very quickly—either they know the space or they don’t. If you’ve worked and lived in the space, you’ll recognize immediately whether an investor knows what you’re talking about. For founders coming from outside insurance trying to build in the sector, Peter’s recommendation: talk to someone like JoAnne who’s helping businesses build in insurance to get expertise yourself before blindly following what an investor recommends.
Look for action, not just promises of access. Omer came from FinTech into insurance, a highly relational, network-driven industry where his team needed access. Many investors pitched access, but it’s very easy to see if they actually have it. Are they making intros? When they make intros, do people immediately respond? You can see it quite clearly, very quickly through the actions they take. For Omer’s team, this was almost a no-brainer requirement—they needed that access and could verify it through observable behavior.
“The simplest thing is to ask for some receipts. Whether to talk to other CEOs of their other portfolio companies, either current or prior... get more tactical examples of where they’ve brought in or sourced talent or leveraged their network to open a few doors.” — Joe Zuk
“If you’ve worked and lived in the space, like we all have, it should be fairly fast and apparent to you whether an investor knows what you’re talking about and follows what you’re trying to do or not.” — Peter Tilbrook
“A lot of investors would pitch access, and it’s very easy to see if they actually have that access... Are they actually making an intro? If they are making an intro, do the people you get introduced to immediately respond?” — Omer Rimoch
Learn more:
Joe Zuk: joezuk.com
Loro: loroinsurance.com
Advance: advancehq.com
Read Joe’s article that inspired this series: Founder’s Due Diligence Guide
Meet us in the comments and share your stories or questions for future episodes. Have you talked to an investor’s portfolio founders before signing? What did you learn?
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