The Raise Starts Before You're in the Room: My Conversation with Sean Byrnes
This week’s episode of Raiser’s Edge features Sean Byrnes, founder and CEO of Flurry and Outlier, coach, investor, and author of the highly regarded The Breaking Point newsletter. Sean has raised over $100M spanning over two dozen venture rounds, and has been an advisor to countless CEOs.
When it comes to how to succeed at fundraising, Sean is relentlessly focused on understanding what’s actually going through an investor’s head — before, during, and after the meeting. That’s led to his repeated success, even when the market was at its worst and companies all around him were closing their doors.
Here’s what Sean’s strategy looks like in practice:
1. Be remembered.
Investors see five or six pitches a day. And most of them end quietly, with a polite thank-you, a vague follow-up offer, and then out the door. What Sean argues for is instead ending with a bang that sparks imagination and excitement - a hook they’ll still remember at the end of the week. You want them walking out of that room thinking about the potential of what you’re building, not just cataloguing the facts of it: What does the world look like if this works? What’s the size of the opportunity they’d be passing on?
Investors will rarely be more passionate than you are, so let your own excitement come through. That’s what gets you a second meeting.
2. Filter for conviction, not convenience.
Founders often make it “easy” for investors, jumping through hoops to meet on inconvenient terms and wasting cycles on lukewarm leads. Sean’s play? Add friction: let investors come to you, meet on your turf, and watch who puts in the effort. The ones who opt in despite the friction are already showing conviction. They’re the ones who will fight for your company.
3. Know their bias.
Every investor who sits across from you has already formed biases based on your space, your category, who referred you, what’s in their portfolio, what bets they’ve made before that worked or didn’t. Sean’s point is that a lot of founders try to overcome that in the room.
The smarter move is to figure it out before you ever schedule the meeting: Who’s already fishing in your pond? Who’s had a win that looks like what you’re building? Who’s been burned by something adjacent and won’t go near it again? That’s the research that actually moves the needle — and most founders skip it entirely.
4. Give the raise full focus.
Don’t fool yourself into thinking you can fundraise “on the side.” If you’re raising, act like it. Treat it as a 3-6 month full-time blitz, not a side project. The founders who try to juggle everything inevitably stretch the process, adding pressure and risking both the business and the raise. Block the time, do the prep, and expect it to take longer than your best-case estimate. Fundraising IS your job now - so plan accordingly.
For more wisdom from Sean, you can listen to his podcast, The Startup Help Desk, and subscribe to his newsletter, The Breaking Point by signing up below. Both are excellent resources for founders and fundraisers looking to get their company through the next round, and to take it to the next level.
If you want to hear from more world-class founders like Sean on what actually moves the needle in fundraising, follow Raiser’s Edge on YouTube, Spotify, and Apple Podcasts. And if you want my top takeaways, frameworks, and stories from each episode delivered straight to your inbox, sign up for our Substack—you’ll get practical wisdom the minute each episode drops.
Stay sharp,
Ben