Leaving the Safe Path to Build Supra: Marc Baselga on Career Courage & Community

What does it really take to leave a stable career and build something of your own?

In this episode of If I Could, Marc Baselga shares the honest story behind founding Supra, a community for product leaders navigating growth, leadership, and career uncertainty. We talk about the fear that comes with stepping off the safe path, the importance of surrounding yourself with the right people, and how Marc turned doubt into momentum.

Marc reflects on the lessons he learned transitioning from product leadership into entrepreneurship, why community matters more than ever for modern leaders, and what he wishes he had known before taking the leap.

If you’re thinking about starting something new, feeling stuck in your career, or questioning whether you’re ready for the next chapter, this conversation is a reminder that clarity often comes after action, not before.

Learn more about Marc's work by clicking on the links below:

• Supra:  https://www.joinsupra.com/
• Marc's Linkedin Profile:  https://www.linkedin.com/in/marcbaselga/
• Insider Loops:  https://www.insiderloops.com/

Contact us: @ificouldpodcast
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Transcript

Host:
Mark, welcome to the show, man. Happy to have you here.

Mark:
Yeah, I’m so excited. I’ve been looking forward to this all week. Thanks for having me.

Host:
Same here. I usually start the show by giving a quick intro. You’re the founder of Supra, correct?

Mark:
That’s right.

Host:
Tell everyone a little bit about what Supra is.

Mark:
Supra is a private community for ambitious product leaders. Our goal is to help members do their jobs better and make stronger decisions through peer support.

We originally focused on product leaders managing other PMs, but we’ve expanded to include senior ICs as well—especially as we’ve seen people move back and forth between leadership and IC roles.

When someone joins Supra, we match them with a peer group of about seven others. The matching is based on three things:

1. Company stage or size – Series A with Series A, big tech with big tech
2. Scope and seniority – not just titles, but team size and influence
3. Ambition – where you want to be in 5–10 years

In addition to peer groups, we run in-person events, speaker sessions, and an active Slack community. Today we have around 400 members.

Host:
And I’ll say this upfront—I’m a proud member myself. It’s been a great environment.

Before Supra, let’s rewind a bit. What were you like as a kid? Did you always see yourself as an entrepreneur?

Mark:
Honestly, I was pretty confused. On my dad’s side, five generations were doctors. My dad was the oldest, I was the oldest—there was definitely pressure.

But biology and science were never my passion. I was social, competitive, curious about how people think and interact. I loved challenges, but I was also very aware of risk. I liked doing hard things, just not reckless things.

I changed majors a few times in college. I started in bioengineering as a compromise, but I was bored. Then I took an intro to computer science class and everything clicked. I could build things, test them instantly, and see results. That feedback loop was addictive.

Host:
How did that turn into a career in tech?

Mark:
In college, I became CTO of a student-run holding company with several real businesses—real estate, shipping, storage, moving services. We were doing real revenue.

People would come to me with problems, and instead of coding everything myself, I enjoyed understanding the problem and figuring out solutions. A friend told me about product management, and that’s when it clicked.

At a career fair, I skipped the massive big-tech lines and talked to a recruiter from a small company at the time—Asana. She recommended Cracking the PM Interview. I read it in a week, followed up, and by sheer timing, they decided to take their first PM intern. That’s how I got started.

Host:
That’s incredible timing—and initiative.

You spent five years at Asana. What led you to start Super?

Mark:
Asana was an amazing place. I saw the company scale from Series B to IPO, surrounded by incredible mentors.

But I wanted to experience earlier-stage chaos. I joined a Series A healthcare startup as Head of Product, and that’s when I felt something new: isolation.

I was making big decisions without the peer support I’d had before. What helped the most wasn’t courses or coaching—it was talking to other heads of product dealing with the same challenges.

That’s when I realized: this kind of peer support is incredibly powerful.

Host:
So how did you go from “this is helpful” to actually building Supra?

Mark:
First, I had to take care of myself. I was burned out, and my dad had passed away six months earlier. I took a few months just to reset mentally and physically.

Then I committed to one year. No quitting. After one year, I could reassess—but not before.

I started with people in my network, ran small groups for free, and asked for brutally honest feedback. If people showed up consistently and got value, I knew there was something there.

Once that worked, I started charging—which was terrifying.

Host:
That’s always the hardest part.

Mark:
It really was. I was uncomfortable asking for money. I got a coach, practiced relentlessly, recorded calls, and did 40 conversations a week just to get better.

Eventually, patterns emerged. I learned what people were willing to pay for and why.

Host:
Now that Supra has scaled, how do you think about the future?

Mark:
I’m very intentional about not scaling past quality. Communities only work if the people are exceptional. Once that breaks, it’s very hard to fix.

We probably have room for a couple hundred more members. Beyond that, growth will come from going deeper—helping people land their next role, advise companies, or use AI effectively in their work.

Host:
Fun question: what do people think you do versus what you actually do?

Mark:
People probably think I just talk to people, post on LinkedIn, and record podcasts.

In reality, Supra is operationally complex—50 peer groups, multiple monthly events, speakers, logistics, fires to put out. I spend a lot of time supporting the team and building systems so mistakes don’t repeat.

Host:
If you could have dinner with anyone, who would it be?

Mark:
Richard Branson. Massive success, but he genuinely seems to enjoy life and family. That balance really inspires me.

Host:
Any funny or unexpected moments along the way?

Mark:
One of my closest collaborators today started by sending me a brutally critical email about my signup form. I could’ve reacted defensively—but I chose curiosity. That turned into a podcast, a side business, and a great friendship.

Host:
Final question: what advice would you give someone inspired to build something of their own?

Mark:
Be honest about your situation. Give yourself a real runway.

Pick something you’d be excited to work on for 10 years.

And ask yourself: What’s the worst that can happen? If you’re okay with that outcome, it removes fear and lets you be bold.

Host:
Mark, this was fantastic. Where can people find you?

Mark:
LinkedIn is the best place — Mark Baselga.
Supra: joinsupra.com
Podcast: Supra Insider
And our new interview prep project: Insider Loops.

Host:
Appreciate you, man. Thanks for coming on.