“The best angels are the ones who can open the next round for you, not just write a check. I look for founders who have done something exceptional before I ever meet them, so make yourself visible by building something worth noticing.”

“I look for angels the same way I look for founders: bet on the individual, not the brand. My early wins came from following the smartest people I already knew from LinkExchange, not from chasing the hottest fund.”

“I spent two decades building deal flow the hard way, and the honest truth is most founders confuse finding angels with finding money. The angels you want are the ones who add value before they add a wire: they make customer intros, help you hire, and show up when the next round is hard. Start with operators who have actually built and sold something in your space, not the local pitch-night crowd.”

“I made most of my angel investments through relationships built over time, not pitch contests or cold emails. The best ones came from founders someone I trusted already trusted.”

“Stop chasing big names. Go find angels hungry for deals in your space—they're in angel groups in your region, on platforms like AngelList where they're actively deploying small checks, and now on community tools like Investor Match that let you run a free match to find fit before you email.”

“I spent my first years in San Francisco going to three or four startup events a week, not to pitch, but to build real founder friendships. Those relationships became the source of every investor intro that mattered.”

“The best angels I've taken money from brought a specific skill I needed, not just a check. Look for investors who've done the thing you need help with, talk to their portfolio founders about whether they actually show up, and remember that trust matters more than brand at this stage.”

“The best angels are not the ones with the biggest names, but the ones who have actually shipped something close to what you are building. I look for people I would want in the trenches with me, then work backward to whether they write checks.”

“I tell first-time founders to stop cold-pitching and start with companies adjacent to theirs. Find who funded those founders, then ask those founders for advice, not an intro. If they believe in you, the introduction usually follows.”