When Two Questions Changed Everything: Inside Our Latest Open Office
- Angel Gambino
- Aug 19
- 3 min read
Some conversations are worth more than a year's worth of generic startup advice. Last Monday's Open Office session proved that point—twice over.
The Room Where Real Problems Get Real Solutions
Angel Gambino doesn't do fluff talks or motivational speeches. As a multi-exited founder, investment banker, and angel investor who's guided thousands of startups through their scaling journeys, she cuts straight to what founders actually need: tactical answers to the questions that keep them awake at night.
Our Open Office sessions follow a simple formula: 15 minutes, live Q&A, no prepared remarks. Just founders with real challenges getting the kind of clarity that typically costs thousands in consulting fees.
The Pre-Revenue Founder's Playbook
Mike M. came with the question every early-stage founder wrestles with: "How do I build my first investor pipeline when I'm pre-sales, pre-revenue?"
Angel's response was pure tactical gold.
Start with 100 investors—but not your dream investors.
"You're going to get the vast majority of no's," Angel explained. "Don't pitch your ideal investor right from the start. You need practice getting the questions, knowing how to respond."
The strategy? Build your list with surgical precision:
Sector alignment (they’ve invested in adjacent, but not competitive companies)
Geography considerations (though this has relaxed post-COVID)
Stage specificity (pre-MVP, pre-revenue, etc.)
Investment thesis match
References from other founders and investors - what is it like to work with this person when things get tough?
Make your outreach impossibly targeted.
"The thing that pisses off investors the most is when you get a pitch where it's clear they haven't done any research," Angel noted. "If I'm going to take money from my pocket to put it in yours—that's taking money away from my son to give it to you—I want to know you've taken time to understand what I'm interested in and that you value my time."
Show momentum without revenue.
For pre-revenue founders, Angel outlined the alternatives: wait lists, freemium usage, distribution lists, letters of intent, pilots. When those aren't available, focus on your defensible moat and unique go-to-market strategy.
Warm introductions aren't optional.
"Some investors will not respond to a pitch where there's not a warm introduction," Angel emphasized.
The best sources? Founders they've already invested in, other committed investors, or—as Angel's favorite story proves—literally anyone in your network who believes in what you're building.
The Mental Health AI Breakthrough
Chisomo M. from a UK-based AI mental health platform for children had already started knocking on investor doors with mixed results. Her question: "What other strategies can we adopt to gain traction beyond what Mike just heard?"
Angel's answer drew from her experience as Chief Product Officer at Ellipsis Health, an AI mental health company.
Turn pilots into proof points.
"Getting pilots secured and executed—and if you can get any part of that pilot paid for, even just a setup fee—definitely shows willingness to pay and that there is a market or at least some kind of demand or need," Angel advised.
The approach treats pilots as customer discovery, not just validation. You might think you're solving one problem and discover an even bigger opportunity.
Target the right partners.
In mental health AI, providers and insurance companies regularly engage in pilot programs. It's standard practice, not a special favor.
Consider white paper validation.
Publishing research in reputable sector publications provides another form of validation that resonates with investors, even without clinical diagnosis claims.
The Meta-Lesson: Quality Over Quantity
Both conversations revealed a deeper truth about successful fundraising: precision beats volume every time.
Whether it's Mike's targeted investor research or Chisomo's strategic pilot partnerships, the founders who break through aren't the ones casting the widest nets. They're the ones who understand exactly what they need, who can provide it, and why it's a great match.
As Angel noted, "You've got to be very, very targeted and personalized in that outreach." The time investment is significant, but the alternative—generic outreach that wastes everyone's time—is worse.
Your Next Move
Fifteen minutes. Two questions. Tactical advice that would typically cost thousands in consulting fees.
This is what happens when you show up with real problems and get answers from someone who's actually solved them. The magic isn't in the format—it's in the quality of both the questions and the person answering them.
Ready to bring your questions to the table?
Our next Open Office session is filling up fast. These aren't massive webinars where you're another face in a Zoom grid. We keep it intimate, focused, and ruthlessly practical.
Can't make it to the next session? Our membership program offers deeper access to Angel's expertise, curated investor connections, and the peer community that actually accelerates your growth.
Because the difference between founders who scale and those who plateau isn't talent—it's access to the right insights at the right moment.
Your breakthrough is one targeted question away.