Category: Angel Investors

Matthew Stafford, professional investor and co-founder of Nine Others, argues that simplicity wins. He shares how starting on the Venture Capitalist side sharpened his founder's empathy, the early signals he listens for, and how one dinner became a global peer network. We unpack the pre-boom London fundraising scene, practical ways to cut noise from your pitch, and the community mechanics that actually move founders forward. --- Episode Resources - Nine Others - Official Website (co-founded by Matthew Stafford) (https://9others.com/) - “What’s Keeping You Up at Night?” by Matthew Stafford & Katie Lewis (https://a.co/d/hMhyJBI) - Overview of Matt & STAFFORD VC (https://www.stafford.vc/?pvs=143)

Cheryl Kellond has built startups from the ground up, survived the crash of a hardware business, raised millions in venture capital, and walked away with battle scars. In this episode, she pulls back the curtain on what it really takes to lead a company through chaos. We get into why hiring fast can backfire, how funding can trap you, and what founders often overlook when chasing growth. Cheryl talks candidly about ignoring her gut, managing burnout, and staying true to the reason she started in the first place. It’s a sharp, honest look at the difference between building a business and building one that lasts. --- Episode Resources “The Hard Thing About Hard Things” by Ben Horowitz (https://a.co/d/9j9DMya)  Tyler Denk’s Beehiv Newsletter (https://www.beehiiv.com/blog/newsletter-behind-the-scenes) 

Reuben Levinsohn, professional investor and founder coach behind Exit Quotient Ventures and Flying with Founders, argues that clarity and discipline win. He shares how starting from an “exit first” mindset sharpens founder focus, the early signals he listens for like EQ, leadership quotient, paid pilots, and a clean path to $1M ARR, and when to graduate beyond founder-led sales. We unpack the red flags that kill momentum, practical ways to earn a second meeting, and the founder-wellness routines that keep you in the game. Along the way, Reuben breaks down what he saw in Pavewise and Protein Pints, and how to turn traction into a real go-to-market engine. --- Episode Resources Flying with Founders: Founder Coaching, Meetups, Retreats. (https://www.flyingwithfounders.com/) Flying with Founders Youtube Channel (https://www.youtube.com/@FlyingWithFounders/videos) Reuben’s Venture Capital: Exit Quotient Ventures (https://www.exitquotient.com/) Webinar event series: “Inside the Mind of a VC / Investor” (https://www.flyingwithfounders.com/fwfevents/inside-the-mind-of-a-vc-customer-satisfcation) Pavewise: AI-assisted planning for paving in relation to weather. (https://www.pavewisepro.com/) Protein Pints: High-protein ice cream startup that Reuben angel-backed. (https://proteinpints.com/) Catalina Crunch: Exec talent the Protein Pints founders recruited from. (https://us.catalinacrunch.com/) “Lift Others as You Climb” by Scott D. Idle (https://scottidle.com/ , https://a.co/d/hvRFPYv) “The Founder’s Survival Guide” by Rachel E. Turner. (https://www.thefounderssurvivalguide.com/ , https://a.co/d/8BkG46M)

Angel investor, author, TEDx speaker, and SEC advisor Marcia Dawood joins me to pull back the curtain on what angel investing really is—and why you don’t need to be a millionaire or a finance expert to get started. She shares what most founders get wrong in their pitch, how to evaluate a startup beyond the hype, and why obsessing over the problem is more important than selling the solution. Whether you’re a founder raising capital or someone curious about investing in early-stage companies, this episode is packed with unfiltered insights you don’t want to miss. --- Episode Resources Marcia’s Podcast: The Angel Next Door (https://www.marciadawood.com/angelnextdoor) Marcia’s Book: Do Good While Doing Well (https://www.marciadawood.com/dogood) “Venture Deals” by Brad Feld & Jason Mendelson: (https://a.co/d/eZTwdZy)

What does it take to walk away from a $15M term sheet? Bob Knorr did just that — choosing ownership, control, and vision over outside capital. He built that company (then 2 others) with a poignant blend of business sense, ethics, and intuition. In this episode we discuss how he built a medtech company from the ground up, bootstrapped it with creativity (and a Costco credit card), and ultimately exited to a publicly traded company. We discuss his other ventures and what he’s learned along the way about hiring the right early employees, developing a go-to-market strategy, and how to stay true to a vision while adapting to reality. Throughout every topic we cover, Bob shares hard-earned wisdom for founders at every stage. --- Episode Resources Check out what Bob is currently building with his company “Timless Tartans” (https://timelesstartans.com)

In today’s episode I talk with Kelly Iannone, an experienced full-time investor who’s built a diverse portfolio across real estate, public stocks, and most recently, early-stage startups. She shares why one of the biggest misconceptions about investing is that you have to do it all yourself, how to spot a founder worth betting on, and why trusting the right people is the real key to hedging risk and achieving 10x returns. If you’ve ever wondered how to get involved in startup investing—or how to avoid the biggest mistakes—this episode is for you. --- Episode Resources Keep up with Kelly (https://www.linkedin.com/in/kelly-iannone-waypointcip)