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When success on paper doesn’t match fulfillment in practice, what comes next?

That’s the question Caren Maio (Gallatin ‘07), founder of Funnel, former Techstars standout, and now co-founder of 100, has lived through more than once. During a recent AMA for our 2025 Summer Launchpad cohort, Caren offered one of the most candid breakdowns I’ve heard on what it really takes to scale, survive, and stay sane as a founder. From navigating the messy middle to confronting burnout head-on, here’s what stuck with me.

1. Just Because You’re Growing Doesn’t Mean You’re Thriving

Caren’s first company, Nestio (later rebranded as Funnel), was a textbook startup success. Part of the first Techstars NYC class, they raised capital quickly, grew revenue, expanded headcount, and checked all the right boxes. But somewhere in the process of the company's success, Caren realized she wasn’t happy.

“We were growing. Investors were happy. But I wasn’t," Caren said. "The stage I loved — zero to one — was over.”

For many founders, the early chaos is energizing. But scaling brings different muscles: process, people management, and long-term operational rigor. When those new demands don’t match your motivations, the job becomes draining, no matter how good the numbers look.

2. Burnout Doesn’t Always Look Like Collapse

Despite (probably) needing the reset after exiting Funnel, Caren didn’t really take a break either! She was advised to pause for six months, but instead, she picked up a 20-hour-per-week advisory gig, became an EIR (entrepreneur in residence, typically an experienced entrepreneur who is temporarily associated with a VC firm to develop new business ideas, and/or evaluate potential investments), and kept working.

Only later did Caren realize the cost of skipping that true reset.

“I didn’t fully stop," she said. "And that caught up with me.”

This is the version of burnout we don’t talk about enough: the slow erosion of motivation, clarity, and joy. Caren’s experience is a reminder that founders need to protect time for reflection, not just execution.

3. The Next Company Only Works If You Actually Care

Caren’s return to founding didn’t happen overnight. It took a year of killing ideas and advising others before the spark returned. She refused to fake it. The bar was high: she wouldn’t build something unless the problem consumed her.

That problem came in the form of rental application friction, fraud, affordability, process bottlenecks. 100 was born from that obsession. She became totally immersed because:

“The best founders I know are problem-obsessed, not solution-driven.”

She likens 100’s experience to TSA PreCheck: a “fast pass” for the real estate rental process. Launched in October 2024, the company raised an $8 million pre-seed round and already has 300,000+ apartment units on the platform.

4. The Venture Treadmill Isn’t for Everyone

Caren’s view on venture capital is pragmatic, not romantic. She’s seen both sides: fast raises with multiple term sheets, and painful processes where the energy just wasn’t there.

“During my time at Funnel (formerly Nestio), the best raises happened quickly, when we didn’t need the money, but it was a good time to invest," she said. "The worst happened when we were running out of cash.”

She’s also clear that not every company should raise venture money. It’s only worth doing if there’s a clear reason to use capital to accelerate something specific; not just to survive.

“You don’t need to raise venture money to be successful. We raised so we could invest faster, not just to stay alive.”

This kind of capital discipline is rare in early-stage circles, and it shows how second-time founders approach the game differently.

5. The Most Dangerous People in a Startup? High Aptitude, Low Attitude

When asked about mistakes she wouldn’t repeat, Caren was blunt: hiring people who are smart but culturally misaligned is a silent killer. The “high aptitude, low attitude” hire slows you down, no matter how skilled they are.

“Those are the most dangerous people in an organization," she said.

It’s a classic early-stage trap, especially when you’re trying to grow fast. But for Caren, team chemistry and founder-market fit aren’t just buzzwords; they’re survival tools.

She’s also been clear-eyed about co-founder dynamics. One of her previous Funnel co-founders stepped away after realizing the new business wasn’t the right fit. Rather than force alignment, they made a clean break, something more founders should normalize.

6. If You’re Not Good, The Company Isn’t Good

Caren’s biggest lesson? The founder is the engine. If they’re not functioning, physically, mentally, emotionally, the company won’t either.

“If I’m not right, the company won’t be either. It’s a marathon.”

It’s easy to forget this in the pursuit of scale. But as she pointed out, being miserable in a company that’s “crushing it” isn’t a win. Her decision to walk away from something successful on paper was one of the hardest, and most important choices she made.

7. Tactical Advice for Founders

Caren's AMA was packed with startup tactics, too. A few standouts:

• Launch early, not late. The first time around, they waited too long and held everything too close. “When we pivoted and shared widely, things got better.”
• Talk to customers…constantly. The best insight she ever got was through relentless customer conversations and by talking to anyone who was willing to hear. 
• Make it easy for people to help. Whether you’re raising or hiring, clarity and ease go a long way. If you need help, make the ask crystal clear. 
• Targeted accelerators > spray-and-pray. Caren went into Techstars with a goal: find people who had done this before. She came out with mentors she still works with.

Final Thought: No One’s Actually “Crushing It”

One of the more honest moments came when Caren admitted she’s never been the kind of founder who says “we’re crushing it.” Even at her peak, she always felt like she could be doing better.

That self-awareness, coupled with her willingness to walk away and begin again, is what makes her story worth studying. It’s not the tale of overnight success. It’s the quieter kind of resilience, the one that sustains itself over a marathon.