From selling his first startup to leading one of the world’s most vibrant entrepreneurial communities, entrepreneur and angel investor Yash Shah’s journey is a masterclass in ambition, resilience, and reinvention.
Born and raised in India, Shah earned a degree in mechanical engineering from Clarkson University before launching his career in Cambridge, Massachusetts, first at TRW and later at Hewlett-Packard. But his entrepreneurial fire burned brighter. He co-founded InteQ with college friend Santhana Krishnan, building it from a bootstrap venture into an exit-ready business sold to CA Technologies in 2010.
Not content to rest on his laurels, Shah co-founded — along with his brother Uday — Jeavio, an enterprise-tech services firm that empowers PE-backed and growth-stage companies to modernize systems, fast-track innovation, and increase enterprise value.
Along the way, he held leadership roles at SevOne (later acquired by IBM) as CTO, and founded Indus Ventures LLC, an angel-investing and advisory firm.
A charter member of TiE Boston for more than two decades, Shah captained the chapter as president from 2022 to 2024 and joined TiE’s global board in January 2025. His tenure has been marked by a commitment to mentoring, sponsorship of TiE Angels and ScaleUp, and advocacy for founders navigating a rapidly evolving tech landscape.
In an exclusive conversation with The American Bazaar, Shah opened up about his entrepreneurial journey, his leadership at TiE, and the lessons learned from navigating the highs and lows of building companies.
The American Bazaar: Thanks for joining us today. Let’s start with TiE Boston — can you tell us about your role there?
Yash Shah: TiE has been an integral part of my entrepreneurial journey. I’ve been involved with TiE Boston — and TiE in general — for more than thirty years. I was one of those early entrepreneurs looking to make connections, find support, and seek out mentors. TiE Boston was a great avenue for that. I attended events, gained a lot of inspiration, and met many successful entrepreneurs I looked up to at the time — people who were much further along in their journeys. Today, I call many of them friends.
Over the years, I’ve had my own significant entrepreneurial journey, with its share of ups and downs, and TiE played a critical role in many ways. I became an ardent supporter and have been involved in various capacities — as a board member, sponsor, program participant, and investor.
Later, TiE approached me about taking on a more strategic role. They asked if I could serve as president, and since I was in the middle of an exit and had the time, I agreed. The TiE Boston presidency is a two-year term, and during that period — when I met Rowena [Kay Mascarenhas], who became executive director — we accomplished a great deal. In fact, we won the Best Chapter Award globally during the Rio Retreat.
TiE Boston is one of the organization’s most successful chapters. We run programs for entrepreneurs at every stage — early, emerging, and established — and have the connections to support them. When my term ended, I handed things over to the next president and joined TiE Global as a trustee, where I now help support the organization’s larger ecosystem.
Tell us about your entrepreneurial journey so far.
I come from an entrepreneurial family. My father was an entrepreneur — not in tech, but in the movie industry in India — and quite successful. In fact, nearly everyone in my family was an entrepreneur in one form or another.
After earning my degree in mechanical engineering, I worked for TRW and then HP. Eventually, a co-founder friend and I decided to leave and start our own company — my first. At the time, I had a three-month-old daughter. Everyone told me, “You shouldn’t start a company now — it’s too risky with a baby.” But our mindset was, if we don’t start now, we may never start. It was a gutsy decision, but we went for it.
That first venture was a consulting company we ran for five years. We started out self-funded, but later decided to scale and raised significant capital — nearly $60 million over multiple rounds. Entering the venture world was eye-opening, but in the process, we eventually lost the company to our investors. After the 2001 crash, they wanted to shut it down. We refused, bought the company back, restarted it, and rebuilt from the ground up.
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In 2010 — after 15 years of bootstrapping, being venture-backed, losing control, buying it back, and scaling again — we had an incredible exit. We had split the business into two units and sold them to separate buyers. That journey taught me the full spectrum of entrepreneurial life: starting from scratch, raising money, cutting costs, restarting, and ultimately exiting. It also gave me deep insight into what to do — and what not to do — which I now share with other entrepreneurs. The experience reinforced my support for TiE and my belief in the importance of having a strong network in what can be a very lonely journey.
After selling to CA Technologies, I stayed on for a while before leaving to start Jeavio. At first, I wasn’t looking to start another company — I was spending time in India caring for my mother. But while there, I thought, why not work on something meaningful while I’m here? I reverse-engineered the idea for Jeavio based on my passions: investing, mentoring entrepreneurs, and building products. We started as a “venture services” company, helping startups with product development, strategy, and execution.
In the middle of running Jeavio, I was invited to be CTO of SevOne, a Bain Capital–backed company. What was supposed to be a short-term engagement turned into a multi-year role, and we ultimately sold SevOne to IBM for $1.8 billion.
Over time, Jeavio evolved. While we still invest in and support early-stage companies, we also now take on larger private-equity–backed projects. The company has grown to more than 300 employees — far beyond my original expectations. Unlike my first venture, Jeavio has no outside investors; it’s entirely owned by my brother and me, giving us the freedom to run it as a long-term platform for delivering services and supporting entrepreneurs.
Jeavio was completely bootstrapped by you and your brother. What would you say are your goals for Jeavio this year or next? Are there any set targets you’re aiming for or specific projects you’re working on?
When you’re a self-funded company, you’re essentially deciding your own future. There’s no outside investor pushing for growth, so you create your own pressure to define what’s next. Jeavio has gone through different phases of growth — initially, the idea was just to stay busy and help people out. But once you start a company, it’s hard to stop. You have to keep growing. It’s not easy to say, “I’ll just sit back and relax,” especially when you know your employees’ futures depend on the company’s success.
Right now, we’re in what I’d call our third phase of growth: we’re rebranding and taking full advantage of the current wave of AI transformation. It’s a lot easier to start companies now because of AI — it can accelerate planning, decision-making, engineering, and more. It’s truly transformative in how quickly you can turn an idea into reality. But even with AI, companies still need guidance.
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So, our growth plan continues. We want to keep expanding and help more companies — not just startups. We’re now working with larger organizations as well, helping them transform their business functions and capabilities by leveraging the latest advancements in software.
In the early stages of your entrepreneurial journey, you experienced all phases of building startups. What lessons or tips would you share with emerging founders, investors, or anyone looking to start a business?
A lot of what I share is about both what to do and what not to do — much of it learned firsthand. I’m not a professional or institutional investor; I consider myself an entrepreneurial support person. I invest to help startups, not with an expectation of returns. Most don’t return anything — that’s just the reality — but I gain a lot of learning from the experience.
The first thing I tell entrepreneurs is that you must become comfortable with the worst-case scenario before you start. If you’re not thinking about what could go wrong — and if you’re not okay with that outcome — you’ll always be making decisions from a place of fear. Too many entrepreneurs try to hedge by “doing it on the side” or “balancing it off.” When we started Jeavio, we jumped in with both feet. Family support made that possible — someone told me, “Give this a shot for six months, and if it doesn’t work, you can get your job back.” That safety net helped neutralize the fear of the unknown, which is critical because entrepreneurship is a lonely journey with ups, downs, and constant decision-making.
The second lesson is the power of networking. You can only plan so much — you need to stay open to ideas, opportunities, and connections that come your way. My co-founder was an extrovert, while I was introverted. Over time, I learned that many of Jeavio’s key milestones — finding customers, attracting investors, even surviving tough times — happened because we were out there networking and building relationships. If you isolate yourself, you risk becoming too narrow in perspective, making it harder to navigate challenges. Relationships with employees, investors, and customers are what you ultimately count on.
And finally, remember that failure is part of success. In entrepreneurship, failure isn’t the end — it’s a learning process. You need grit to stay on the path, pick yourself up, and keep going. It’s much easier if you have a co-founder who complements your skills and can serve as a sounding board, rather than trying to go it alone.
AI is taking over everything. Are there any trends or sectors you’re especially excited about?
AI is a huge space right now. Every time new capabilities emerge, they create a wave of opportunities and business models we can’t even fully imagine yet. Think about life before the internet, before mobile, before touchscreens — AI has that same potential to transform everything.
It can be a headwind or a tailwind for companies, depending on how they adapt and leverage it. People are understandably fearful because AI is becoming so capable — it can communicate almost like a human. You might not even be talking to me right now; you could be talking to my AI avatar. That can be unsettling, but from both an entrepreneurial and investment perspective, the potential value is massive.
At Jeavio, we’re helping industries from legal to medical completely transform with AI — from customer service to help desks — largely because AI can communicate in ways that were never possible before. And it’s not just about GPT. I was at the MIT AI conference yesterday, and they were talking about the “internet of agents.” That’s what they’re calling the next internet — an interconnected network of AI agents.
When it comes to investing, I tend to focus on sectors I know, but I also back companies in industries I’m not an expert in. That allows me to learn. I’m not a professional investor — I’m an angel investor — so most opportunities come to me rather than me actively hunting for them. I invest based on gut: if I like the idea, the team, the people, and their potential, I’ll back them. I look at the founder’s background, their commitment, the size of the problem they’re tackling, and their ability to lead a team.
Overall, I see AI as a massive tailwind for nearly every industry. Over time, it will create huge opportunities across the board.
What kind of businesses do you usually approach? What is it that convinces you to invest in or look into a business or a startup?
I don’t actively seek out opportunities. Typically, someone reaches out — often through a referral — because they have an idea they want to pursue. I invest in multiple ways: sometimes directly with cash, and other times indirectly by providing services through Jeavio to help bring their vision to life. For example, if someone says, “I have this vision, but I don’t have the money for it,” I might invest, assemble a team for them, and say, “Okay, let’s try this out,” giving them the capabilities to raise funds and clearly articulate their plan. Many people come to me for engineering or product help, but as I mentioned earlier, my decision is always a gut call. I don’t make massive bets — just enough to get things started. I’m often the first to write a check, to signal what’s possible, and these journeys almost always take time to unfold.
Were there any major challenges or missteps you’ve seen entrepreneurs encounter and learn from?
Good question. I come from a product background, and many of the entrepreneurs I talk to are domain or technology experts — whether in medical, life sciences, or tech. They know their field inside out. One mistake I’ve made, and I’ve seen others make, is underestimating what it takes to sell and market a product versus building it. Building the product is often the easiest part — and sometimes we over-engineer it, thinking that’s where most of the work lies. In reality, the real challenge is selling it. Too often, not enough time is spent figuring out who will buy it and why. Instead, the product gets burdened with complexity, trying to solve too many problems at once, and ends up solving none effectively.
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Interestingly, when a salesperson or marketer — not a domain expert — starts a company, they often do better in this regard. They know the problem to solve, stay focused, understand the economics, and know how customers buy. That focus can make all the difference.
The second challenge is funding. Many entrepreneurs believe they must finish the product before raising money, but once it’s built, investors often ask to see customers first. VCs want to minimize risk, and this back-and-forth can frustrate founders who struggle to sell the idea without traction. This may be even more common now as funding has tightened and investor expectations have shifted.
Finally, product experience is often underestimated — the look, feel, and emotional connection it creates. First impressions matter. Customers should fall in love with the product at first sight, and it must perform its core job exceptionally well. I’ve seen (and experienced) situations where under-investing in these areas led to lower returns. In hindsight, spending more upfront on product experience could have tripled the eventual exit value.
What does success mean to you personally, and what does it mean when you look at the new entrepreneurs you support?
Success means different things at different stages of life. I was reading a book called “The Psychology of Money,” which talks about the cost and chase of money. Another definition of success asks three questions: Are you working on something you enjoy? Are you working with people you enjoy being around? And are you in control of your time? If you can answer “yes” to all three, that’s success.
By that measure, I don’t need to answer to anyone. I control my own time, I’m doing work I love, and I enjoy the people I work with. I don’t wake up thinking, “Oh my God, I have to deal with this.” That’s not my reality. Everyone has to define success for themselves, and that definition will evolve over time. For me, there was a period when it was about financial security — making sure my kids had enough to survive and sustain themselves, and hitting those financial milestones.
For the entrepreneurs I support, I define success as achieving product–market fit. The faster they get there, the more likely they are to achieve commercial success. It’s not just about the money raised; I’ve seen companies raise millions and still fail to find the right product, while others raise little and thrive. The difference comes down to understanding who will buy, why they’ll buy, and grasping the nuances of the market. If you achieve product–market fit, you can repeat and scale it — even without the founders’ day-to-day involvement. That’s the kind of success I push entrepreneurs toward.