Q3 Tweener Founder Spotlights: Why We Build
Check out short interviews with our new Tweener portfolio companies: the spark, the struggle, and the next steps.
Tweener Founder Spotlights
We’re bringing you something new! Our Founder Spotlights series tells the stories behind the startups, the human side that rarely makes it into pitch decks or press releases. Every founder has a reason they chose entrepreneurship. Maybe it’s a problem that kept them up at night or a moment that pushed them to try anyway. All have picked up lessons along the way.
Instead of funding stats or product specs, this series dives into motivation, challenge, and community. Why do founders do what they do? How do they push through the tough days? What have they learned that could help the next builder?
These conversations aim to capture that “why” to remind other founders that they’re not alone, they’re not crazy, and that the path to building something meaningful is never linear, but it’s always worth it. It’s also a celebration of the Triangle startup spirit: collaboration over competition, progress over perfection, and stories that make the journey feel a little less lonely.
Q3 had 9 new investments! We’ll be featuring Founders and their companies in these Spotlights. Up first? FutureProof: “AI-powered CFO” for startups, founded by Oz Merchant.
Thanks to our sponsors for sponsoring this post:
Lithios Apps - Lithios Apps is a Triangle-based software design and development studio that builds custom mobile and web applications focused on quality and user experience. We help founders and teams bring products to life that drive growth, engage customers, and stand out in competitive markets. We’ve worked side by side with clients whose products have gone on to earn millions in follow-on funding.
ExtensisHR - As a Professional Employer Organization (PEO), ExtensisHR empowers tech founders and growing businesses to scale smarter. We take HR administration off your plate—managing payroll, recruiting, employee benefits and retirement plans, compliance, risk, and more—so you can focus on innovation. For over 25 years we’ve leveraged a people-first approach, customer-centric mindset, and deep industry expertise to ensure employers have the tools needed to stay competitive in today’s market.
Bank of America – BofA’s Transformative Technology Group helps game-changing tech businesses and founders realize their boldest ambitions across a wide range of technology sectors. With hands-on support, world-class resources, and an extensive network – BofA provides the stability and scalability that tech companies need to rapidly grow today and into the future.
Robinson Bradshaw - A full-service business law firm with a passion for supporting the Triangle entrepreneurial ecosystem. Learn more about Robinson Bradshaw’s startups and venture capital practice here.
EisnerAmper (formerly HPG) - One of the world’s largest business consulting firms, with a dedicated technology practice offering outsourcing, accounting, tax, and advisory services. Our experienced professionals serve more than 2,000 technology companies, from early-stage startups to public enterprises. Discover how EisnerAmper’s stage-specific solutions and industry expertise can help you achieve your milestones whether startup, international expansion, M&A, or IPO: eisneramper.com/tech.
Stacking the deck for founders: Oz Merchant on building Futureproof
Lessons You’ll Hear Between the Lines
Oz’s story is packed with founder wisdom. Here’s the short version before you dive into the details:
Re-write the playbook. What worked last cycle might be your blind spot now.
Validate hard, then build fast. Talk to 50 customers before you ship.
Design for the decider. If the founder can’t use it, it’s the wrong UX.
Teach while you ship. Explain why a metric matters for this model.
Lean on the community. Every time you give back, it comes back stronger.
As founders, we’re great at solving the big problem we see in the world. Finances? Not usually one of them.
That gap is what pulled Oz Merchant to start Futureproof, a financial operations platform built from a founder’s point of view. Oz has been around the Triangle for years, running pitch nights, mentoring founders, and helping accelerators. He’s seen the same pattern on repeat: brilliant builders losing sleep (and sometimes companies) because they couldn’t clearly see cash, burn, and runway.
“Most startups die because they run out of money. If we give founders better visibility, day-to-day cash, burn, runway, we improve their odds.”
Oz in fundraising mode visiting San Francisco during Tech Week
The spark: “Why am I still teaching this in spreadsheets in 2025?”
The idea for Futureproof came together over a whirlwind weekend.
On a Friday, Oz Merchant was recording an eCommerce podcast, talking about what it takes to scale from a seven-figure business to eight. In the middle of the conversation, he caught himself saying, “You’ll eventually need a CFO, someone who can think six to twelve months ahead. There’s product creation, sure, but also the logistics of actually having the money.”
That same week, he was mentoring a startup team through a three-year, bottoms-up financial model. In spreadsheets.
“It hit me. Why am I still helping founders do this manually? There’s got to be a better way.”
That realization kicked off a weekend-long brainstorm around CFOs, AI, and founder-friendly finance. By Sunday, the name, concept, and first product thesis for Futureproof had crystallized, all inside 48 hours.
From idea to reality
Momentum came fast, but Oz set a rule: no code until 50 founder interviews. Those conversations helped Oz understand where founder’s financial pain actually lived in areas like bookkeeping, forecasting, planning, and decision-making.
Once the signal was clear, the team built quickly, but even that process became a lesson in adaptability.
“The reality is, the world keeps changing. Just because you had a playbook that worked before doesn’t mean it’ll work the next time around. Everything else has changed, your tools, your market, even your team.”
What you know can help you start, he says, but it can also limit you. Each cycle demands a fresh look at assumptions.
“QuickBooks has been around since 1992. We built a competitive product in under five months. That just wasn’t possible in earlier eras. And now, with the pace of AI, my team tells me, ‘The thing we built last month? With ChatGPT’s latest update, we could do it in a day.’ It’s wild. You have to constantly revisit your assumptions and ask: does this still hold true for the future we’re heading into?”
For Oz, that mindset of continually revisiting your assumptions is what keeps him adaptable and future-ready as a founder, and directly shapes how he builds Futureproof.
Oz is clear: he’s not a CFO, and that’s a feature, not a bug. The product is built by a founder, for founders to make understanding business finances simple, not intimidating.
“We’re our own customer, customer zero. If it solves my founder needs and stays approachable for founders, we’re on the right track.”
Education is baked in, too. Not every founder comes through an accelerator, and not every metric matters to every model. Futureproof teaches the ‘why’ behind the numbers. For Oz, helping founders understand their numbers means helping them understand their business.
Oz hanging with fellow founder (and potential customer!) Gabe Hillegass, who’s based out of Charleston, at the NextGen Summit.
Why the Triangle (again and again)
Oz has left the Triangle more than once, moving to different cities, even different countries, but he always finds his way back.
“There’s a magnetic pull here. Over 25 years I’ve watched the ecosystem blossom. People who had exits stayed, reinvested, and showed up. The culture is collaborative, not cutthroat.”
That collaborative spirit, he says, is what makes the region special. Founders, mentors, and investors genuinely pay it forward. Oz has seen it from both sides: as a founder receiving guidance and as a mentor helping the next wave through programs like Founder Institute.
It creates a ripple effect that strengthens the community every time someone shares what they’ve learned.
“You’re paying it forward, others are paying it forward to you, and it’s just builds on top of it.”
What’s next
Futureproof has early customers live and a full platform rolling out: AI-assisted bookkeeping, forecasting & planning, cap-table modeling, and a built-in data room. It’s a single financial operations layer so founders aren’t juggling five tools and ten tabs.
The mission stays simple: help founders make better decisions, earlier.
Find Oz on Linkedin and see what he’s doing at runfutureproof.com. Explore more Tweener portfolio stories at tweenerfund.com.
Next on Tweener Founder Spotlights
We’re featuring founders solving real problems with grit, heart, and community at their back.
That’s the spirit we’re here to spotlight and the story we’ll keep telling. Stay tuned for the next Tweener Founder Spotlight, highlighting more Q3 portfolio companies.