Jamie Cuffe is the founder of Pace, a former Sequoia data scientist and serial founder who's built investor relationships across multiple ventures.
Patrick Girouard is the founder of District Cover, an InsurTech company that has successfully navigated multiple rounds of financing.
JoAnne Artesani is the Founder & CEO of Sproutr, bringing experience from AIG and Hippo to the MGA world.
Omer Rimoch scaled PayEm from 2 to 45 people and raised $47M and beyond and is Co-Founder & CEO of Advance.
Grace Hanson is a founder who scaled Seagull Cognition and is now building Elysian.
Peter Tilbrook is the Founder of Loro and host of "Age of the MGA" podcast, navigating his first venture.
In this episode of FounderLM, Marissa Buckley asks six founders to complete one sentence: “You know they’re the right investor for your company when...”
Their answers reveal important signals. From decade-long alignment to the feeling you get when their name appears on your calendar, this is the culmination of everything this series has been building toward. It’s a practical checklist of what to look for when evaluating the most important partnerships in your company’s journey.
Jamie: When they’re in it for decades, not just years. If you’re building something truly generational that will transform your industry, you need someone who sees it that way too. This is your life’s work. You want someone up to the scale of your ambition. They’re demanding but supportive, pushing you to be your best, and along for the journey on the order of decades. Otherwise, they might not be there as often or as strongly as you need.
Patrick: When you’re excited to see their name on your calendar. The calendar test is simple but powerful: If you see an incoming call or meeting scheduled with them, are you excited and looking forward to it, or dreading it? If you’re dreading it, they’re probably not the right investor for you personally. Your gut reaction tells you everything about whether this is the right partnership.
JoAnne: When they can pitch your business better than you can. When you hear your business repeated back to you, more succinctly, more eloquently, more targeted, it’s incredibly telling. It means they’ve invested the time to understand the depth of your business. This signal reveals whether someone has genuinely engaged with what you’re building or is staying at the surface and just going through the motions.
Omer: When they’re as excited about your business as you are. Excitement is the baseline. The entire team you hire should be super excited about the business. That’s how you keep them happy and working long hours to support what you’re building. Happy, driven, excited people propel things forward. Negative outlooks create friction and make everything harder.
Grace: When they believe in your vision, not just see a transaction. If they believe in what you’re building, they’ll be there for you. If it’s a mechanical, transactional exercise, they’ll want out at the first opportunity or pressure you to deliver outcomes you don’t want. Grace experienced perfect alignment when an investor had written a white paper predicting exactly what she was building. They said, “Wow, you’re building what we thought would win.” That’s the kind of vision alignment that creates true partnership.
Peter: When they push you to an acceptable level of discomfort. Especially when you have co-founders from the same world or company, you can fall victim to being an echo chamber of the same vision and ideas, regardless of whether they’re right or wrong. You need an investor who challenges you, pushes new ideas and thoughts, and prevents groupthink. And as long as it doesn’t completely derail your vision.
“When there’s someone you wanna work with for decades... You have to be building this for decades. This is your life’s work. And you want someone that also sees it that way, that’s up to the scale of your ambition.” — Jamie Cuffe
“If I had an incoming call from them or if I saw that there was a meeting scheduled with them on my calendar, would I be excited and really looking forward to it, or would I be dreading it? And if I am dreading it, it is probably not an investor that is right for me personally.” — Patrick Girouard
“When they can pitch my business better than I can, when I hear it repeated back and it’s more succinct, it’s more targeted, more eloquently stated, I get really excited because it means they’ve invested the time to understand the depth of my business, not the surface.” — JoAnne Artesani
“They have to be excited about the business as you are... people that are happy, driven, and excited usually propel and progress things forward.” — Omer Rimoch
“They have to believe in what you’re building. ‘Cause if they believe in what you’re building, and it’s a mechanical transactional exercise for them, they’re not gonna be there for you.” — Grace Hanson
“They push you to an acceptable level of discomfort... you need someone as an investor that does challenge you a little bit and does push new ideas and new thoughts into you, as long as it doesn’t completely derail your vision.” — Peter Tilbrook
Learn more:
Pace: withpace.com
District Cover: districtcover.com
Sproutr: sproutr.com
Advance: advancehq.com
Elysian: elysian.is
Loro: loroinsurance.com
Meet us in the comments and share your stories or questions for future episodes. How do YOU know when you’ve found the right investor?
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.