Here’s what nobody tells you about entrepreneurship: the win is never as sweet as you think it will be. And the journey? It’s harder, longer, and more relentless than any Forbes cover story will ever reveal.
Jason Saltzman knows this intimately. With two successful exits, over $150 million raised across ventures, a decade of mentoring at Techstars, and co-chair of MIT’s REAP program, Jason has lived the entrepreneurial grind—and come out the other side with wisdom that every business executive needs to hear.
His current venture, Relief, is tackling one of the most pressing crises of our era: crushing consumer debt. One in three Americans has fallen behind on their bills—the highest delinquency rate since the 2008 recession. But this isn’t just a statistic. It’s millions of people losing dignity, drowning in compound interest, and trapped in a system designed to keep them there.
Relief is a financial technology app that automates debt negotiation, saving users up to 70% of their total debt with a few clicks—no phone calls, no expensive firms, no shame. In eight months, over 100,000 people downloaded the app, enrolling $6 billion in debt on the platform.
But Jason’s story isn’t just about building a successful fintech company. It’s about the unsexy truth of entrepreneurship: the daily grind, the relentless problem-solving, the turbulence that comes with rare air, and the realization that success is less about the exit and more about the moment you’re in right now.
For business executives—especially those building, scaling, or contemplating their next venture—Jason’s journey offers three critical takeaways that will reshape how you think about success, resilience, and the work that actually matters.
Takeaway 1: The System Is Broken—And That’s Your Market Opportunity
Jason didn’t stumble into the debt relief space. He’s been in it for 25 years. He’s seen the system from every angle. And his thesis is urgent: we’re in a consumer recession that nobody’s talking about.
The Hidden Crisis
While Wall Street hits record highs, average Americans are drowning. Here’s why:
- Inflation has quadrupled the cost of everyday goods over the past five years. Eggs, gas, groceries—the memes are real, and people feel it.
- People are putting everyday expenses on credit cards at rates never seen before. Not luxury purchases. Groceries. Fuel. Necessities.
- Delinquency rates have skyrocketed to historic levels. One in three Americans has an account in collections.
This isn’t about irresponsibility. Jason is blunt: “Irresponsibility is a fraction of what the real problem is here.”
The real problem? A system designed to trap consumers in financial slavery through compound interest, predatory lending practices, and a complete lack of financial education.
The Credit Card Trap
Jason’s insight: “There’s a reason you learn how to dissect a frog in high school, but you don’t learn how to use a credit card.”
Credit cards are simple to use but devastatingly complex financial instruments. And corporations spend trillions of dollars to get you hooked:
- Credit card booths at career fairs outnumber actual job recruiters.
- Sports events, concerts, retail stores—everywhere you turn, there’s a credit card offer with a dopamine-triggering incentive: 10% off, free flights, stuffed bears.
- Behind every “sign here” is a boardroom decision designed to exploit behavioral psychology and lock you into a cycle of minimum payments that will have you paying for today’s groceries for the next 20 years.
The fine print? Most people never read it. And even if they do, they don’t understand the systemic ramifications of compound interest working against them.
The Medical Crisis Multiplier
Jason and I discussed a pattern we both see constantly: good people with good jobs who fall into debt because of a medical crisis.
- Husband and wife, both employed, reasonable income, own a home.
- Then a medical emergency hits. Insurance doesn’t cover everything. Bills pile up.
- Suddenly, they’re 30-90 days away from catastrophe.
This isn’t the 1%. This is average America. And it’s happening at unprecedented rates.
Why This Matters for Executives
If you’re building a business, broken systems are market opportunities.
Jason saw a system that:
- Forced people to pick up the phone and negotiate with aggressive collectors
- Required expensive firms to negotiate on their behalf (often charging 20-30% of the debt)
- Left millions of people trapped because they didn’t know their debt had been sold for pennies on the dollar—and that savings was available if they just knew how to access it
So he built Relief: an app that automates the entire process, charges a fraction of traditional firms, and only charges if you get savings. Guaranteed results. No phone calls. No shame.
In eight months: 100,000+ downloads, $6 billion enrolled, 50-70% average savings.
Practical executive moves:
- Identify broken systems in your industry. Where are customers frustrated? Where are processes inefficient, expensive, or exploitative?
- Ask: Who’s being left behind? The best market opportunities often serve underserved or overlooked populations.
- Build for dignity. Jason’s insight: “You see the dignity that’s lost along the way.” Solutions that restore dignity create fierce loyalty.
- Leverage technology to democratize access. What used to require expensive intermediaries can often be automated, scaled, and made affordable.
Takeaway 2: It Took 10 Years to Look Like an Overnight Success—Embrace the Grind
Jason’s mantra: “It took me 10 years to look like an overnight success.”
This is the unsexy truth of entrepreneurship that Forbes covers never capture. Every “overnight success” you see is the result of years—often decades—of grinding, failing, pivoting, and fighting.
The Daily Reality: Put On Your Boxing Gloves
Jason’s description of entrepreneurship: “Every day I wake up, put on my boxing gloves, and get in the ring.”
You’re not building a business to work for yourself or have more free time. You’re signing up to be a relentless problem solver. You go from one problem to the next. That’s the job.
If you’re under the illusion that entrepreneurship is:
- Easier than a 9-to-5
- A path to quick wealth
- A way to escape hard work
Buckle up. That’s not reality.
The Universe Will Test You
Jason’s insight: “If you’re building something out of nothing, the universe is gonna test the crap out of you.”
Every venture—no matter how experienced you are—comes with relentless challenges:
- Funding falls through at the last minute
- Key team members quit
- Regulatory hurdles appear out of nowhere
- Competitors copy your model
- Customers don’t behave the way you predicted
The difference between successful entrepreneurs and failed ones? Successful entrepreneurs keep fighting.
Rare Air = Turbulence
Jason’s saying: “When you’re in rare air, there’s gonna be turbulence.”
If you’re doing something special—building something innovative, disruptive, or impactful—you’re going to face resistance. From the market. From competitors. From regulators. From your own team. From yourself.
That turbulence isn’t a sign you’re on the wrong path. It’s a sign you’re doing something that matters.
The Exit Is Never What You Think
Jason has had multiple exits. He’s raised over $150 million. He’s invested in companies and founders he cares about. But here’s his truth:
“The wins are never as sweet as you think they’re gonna be. It feels good for about a half a second, and then you’re back into it.”
He hasn’t retired to a beach. He’s still working. And even if he could retire, he probably wouldn’t. Because the work—the moment, the problem-solving, the impact—is the point.
If you’re building a business for the exit, you’re missing the entire journey. And the journey is all you actually have control over.
Why This Matters for Executives
If you’re leading a business—especially a startup or scale-up—you need to get resolved in the grind.
Practical executive moves:
- Reframe success. It’s not the exit. It’s the daily work. Are you proud of what you’re building today?
- Normalize turbulence. Challenges aren’t anomalies. They’re the job. Build resilience into your culture.
- Focus on the moment. You can’t control the future. You can control what you do right now. Pour your heart into that.
- Celebrate small wins. Don’t wait for the exit to feel successful. Celebrate milestones, breakthroughs, and progress along the way.
- Build for the long haul. If you’re not prepared to grind for 5-10 years, don’t start. Entrepreneurship is a marathon, not a sprint.
Takeaway 3: Success Is Setting Yourself Up for Luck—And Luck Favors the Present
Jason’s most profound insight: “Success is a lot of luck, too. It’s not just about making the right moves. It’s having the wind blow in your direction the right way. Success is setting yourself up for luck.”
This is the paradox of entrepreneurship: you can’t control outcomes, but you can control your positioning.
The Moment Is Now
Jason’s life hack: “Focus on the moment. That’s where you have full awareness. That’s where you prove everything to yourself.”
Not tomorrow. Not a year from now. Not at the exit. Right now.
When you focus on doing the best possible thing in this moment—with your goals in sight, your KPIs clear, your mission front and center—the end result comes out better anyway.
But more importantly, you maintain your peace of mind. Because worrying about the future is worrying about everything. And that robs you of your freedom.
The Bigger Picture: We’re All Exiting
Jason’s perspective: “We’re not just exiting businesses. We’re also exiting this earth at some time. On the bigger scheme of things, we’re basically micro dust.”
This isn’t nihilism. It’s clarity.
You won the lottery already. You’re here. You’re alive. You have the skills, the network, the access to capital, the opportunity to build something that matters.
So make what you will of it.
Benevolent Work: MIT REAP and Beyond
Jason doesn’t just build businesses. He invests his time in benevolent projects that solve large-scale problems.
As co-chair of MIT’s Regional Entrepreneurship Acceleration Program (REAP), Jason works with regions around the world to:
- Cut red tape
- Get the right stakeholders in a room
- Think outside the box
- Solve systemic challenges that impact entire ecosystems
For example:
- Botswana is facing a GDP crisis because natural diamonds (their primary export) are being disrupted by lab-grown diamonds. REAP helps them identify new revenue streams.
- Miami is having a moment—mass migration, economic growth—but lacks a clear innovation identity. REAP is building frameworks to define what Miami stands for and how it can lead.
Jason also served on the board of Florida International University to raise endowment funds. He mentors at Techstars. He DMs with founders and people in financial crisis all day long.
Why? Because if you have the means, the only right thing to do is help solve problems.
Why This Matters for Executives
You can’t control luck. But you can position yourself to catch it when it comes.
Practical executive moves:
- Do the best work you can right now. Not for the future payoff. For the integrity of the work itself.
- Build relationships and networks. Luck often comes through people. Invest in your community.
- Stay visible. Share your work. Speak. Write. Teach. Luck favors those who show up.
- Give back. Mentor. Advise. Invest in others. Benevolent work compounds in ways you can’t predict.
- Maintain peace of mind. If you’re sacrificing your mental health, relationships, or values for the business, you’ve already lost.
The Bigger Picture: Building Solutions When the System Is Broken
Jason’s journey is a masterclass in mission-driven entrepreneurship.
He didn’t build Relief because debt negotiation was a hot market. He built it because millions of people are suffering, and he has the skills and network to help.
That’s the throughline in everything he does:
- Relief: helping people escape financial slavery
- MIT REAP: helping regions solve systemic economic challenges
- Techstars mentorship: helping founders navigate the grind
- Board work: helping institutions raise capital for impact
When you have access to capital, skills, and networks, the only right thing to do is solve problems that matter.
The Incremental Build
Relief didn’t launch with every feature. It started with one: automated debt negotiation for accounts in collections.
Next on the roadmap:
- Consolidation loans
- Pre-collection workouts
- Expanded financial tools
Jason’s approach: build incrementally. Prove value. Scale.
This is the pragmatic path for startups. You don’t need to solve everything on day one. You need to solve one problem exceptionally well—then build from there.
The Executive Playbook: What to Do This Quarter
If Jason’s insights resonate, here’s where to start—this quarter:
- Identify a broken system in your industry. Where are customers frustrated? Where are processes exploitative or inefficient? That’s your opportunity.
- Get resolved in the grind. Entrepreneurship is daily problem-solving. If you’re not prepared for that, don’t start. If you are, embrace it.
- Focus on the moment. What’s the best thing you can do right now? Pour your heart into that. The future will take care of itself.
- Build for dignity. Solutions that restore dignity create fierce loyalty. Ask: How does my product/service make people feel?
- Set yourself up for luck. Build relationships. Stay visible. Do great work. Share it. Luck favors those who show up.
- Give back. Mentor. Advise. Invest in others. Benevolent work compounds in ways you can’t predict.
- Celebrate the journey. Don’t wait for the exit to feel successful. Celebrate progress, milestones, and the work itself.
Final Thoughts: The Unsexy Truth and the Beautiful Work
Jason’s journey is a reminder that entrepreneurship is not glamorous. It’s not easy. And the exit—if it comes—is never the fairy tale you imagined.
But the work? The daily grind of solving problems, serving customers, building something from nothing? That’s where the meaning lives.
For executives, the mandate is clear:
- Embrace the grind. Turbulence is part of rare air.
- Focus on the moment. That’s where you have control—and where you prove everything.
- Set yourself up for luck. Do great work. Build relationships. Stay visible.
- Build for impact. If you have the means, solve problems that matter.
Jason’s mantra: “It took me 10 years to look like an overnight success.”
The journey is long. The challenges are relentless. The exit is unpredictable.
But if you’re doing work you’re proud of, serving people who need you, and building something that matters—you’re already winning.
Executives, the moment is now. The work is hard. And the only right thing to do is put on your boxing gloves and get in the ring.
That is the work. And it’s entirely within your reach.
Listen to the full episode on C-Suite Radio: Disrupt & Innovate | C-Suite Network
Watch the episode: DI 126 Navigating the Debt Crisis with Jason Saltzman
This article was drafted with the assistance of an AI writing assistant (Abacus.AI’s ChatLLM Teams) and edited by Lisa L. Levy for accuracy, tone, and final content.
