Grace Hanson is a founder who scaled Seagull Cognition and is now building Elysian. After meeting with 150+ investors, Grace brings hard-won insights on choosing partners who can deliver on execution support, not just capital. JoAnne Artesani is the Founder & CEO of Sproutr, bringing experience from AIG and Hippo to Sproutr offering end-to-end insurance program design, including placement and carrier onboarding. Peter Tilbrook is the Founder of Loro, a specialty insurance solution and host of “Age of the MGA” podcast, navigating his first venture and asking the questions every first-time founder needs answered.
In this episode of FounderLM, Marissa Buckley brings together Grace Hanson, JoAnne Artesani, and Peter Tilbrook to tackle a critical question: How do you actually assess whether an investor can support execution, not just say they can? Grace shares her experience choosing between competing term sheets—and the specific questions that revealed which investor had the infrastructure to deliver. JoAnne offers guidance for first-time founders who don’t yet know what to ask, and Peter brings the perspective of someone navigating fundraising for the very first time. This is execution over capital in practice.
This is episode 4 of 10 in a series of short conversations with 7 different founders and leaders sharing advice and real lessons learned while raising capital. In this series, you’ll get to know:
Grace Hanson, former founder of Seagull Cognition, now founder of Elysian
Omer Rimoch, who scaled PayEm from 2 to 45 people and raised $47M, now CEO 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 “how” when investors promise support—the answer reveals who can actually deliver. Grace had competing term sheets and chose based on real evidence. When an investor said “we can support you in go-to-market,” she asked how. They showed her their team, explained exactly what they do, and introduced the person who would work with her on sales. After closing? They delivered. The investor who couldn’t provide specifics was hands-off with a focus on exit.
It takes time to learn what you’re looking for—and that’s okay. Grace met with 150+ investors before recognizing the patterns. Early on, she thought she was just trying to get money as fast as possible. But the more conversations she had, the more she realized some investors she definitely didn’t want to work with—and a few who stood out as true partners. First-time founders aren’t in a position to know what to ask or what’s even possible to expect. That’s why shopping around is essential.
Go shopping for investors like you’d shop for any major business decision. JoAnne emphasizes that first-time founders should have many conversations to build an inventory of what’s possible. Start thinking about the gaps in your business or capabilities that could be supplemented by a partner. Don’t settle for the first, second, or third conversation. The right partnership is a complementary pairing for both parties, but you won’t find it if you don’t know what you’re looking for.
Be clear on what you actually need: execution support or just capital. There’s nothing wrong with an investor who’s hands-off if you only need capital to reach a certain milestone. But if you need help with go-to-market, sales, or other execution challenges, you need to vet for that specifically. Ask to see the team, the process, and who will work with you. Real support requires real infrastructure.
“When they said ‘we can support you in go-to-market,’ we asked questions like how, and they said, ‘We have this team of three people. This is what they do. This is how they support you’... And in fact, afterwards, they did in fact deliver” — Grace Hanson
“Don’t settle for the first or second or third conversations that you have. Go shopping. Start learning and creating an inventory of what is possible... Start really identifying what’s the right level of partnership for you.” — JoAnne Artesani
Learn more:
Elysian (Grace’s current venture): elysian.is
Sproutr: sproutr.com
Loro: loroinsurance.com
Meet us in the comments and share your stories or questions for future episodes.
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