Former Wall Street executive Tariq Khan explains why he prefers “boring” businesses over trendy AI startups, and shares his contrarian approach to spotting the next big opportunity 

By Asif Ismail

As an angel investor, Tariq Khan is always in search of ideas and products that “go against the current.” Over the years, he has built a portfolio spanning diverse industries — from health care and artificial intelligence to gaming and pet tech. He co-founded Games24x7 Inc., now India’s largest online gaming company, helping steer the business from concept to market leader. That success cemented his reputation as someone who can spot trends just before they take off.

Khan’s other investments include Buddi-Health, an AI-powered health care platform; and Baby Destination (now known as Convosight), a parenting community network.

He is also a seasoned expert in handling early-stage startups. Khan spent two decades working inside some of the world’s most prominent financial institutions, including Credit Suisse, Morgan Stanley, Lehman Brothers, Citigroup Private Bank, and GM Asset Management. His roles spanned settlements, risk management, compliance, finance, and technology, giving him a holistic view of how global finance operates.

Khan grew up and worked in Rome, Italy, and moved to the United States in 2000 and now lives in the New York City area.

One of his roles was as president of the New York Chapter of TiE (The Indus Entrepreneurs), the world’s largest entrepreneur mentoring network. Under his leadership, the chapter expanded its reach, connecting founders with investors and developing mentoring and education programs for budding entrepreneurs.

In this interview, Khan delves into his investment philosophy, how the roadmap of angel investing has evolved over time, and the AI wave, among other topics. This is the first installment of a two-part interview series. Read the second part, where Khan reflects on his experience investing in India.  The interview has been edited slightly for clarity and readability.

Asif Ismail: You’ve had some incredible success as an angel investor, including backing a unicorn. When you choose a company, do you prefer that the founder has experience working for another company, or do you like someone fresh out of school?

Tariq Khan: What I look for more is the right mix of skills. One individual is unlikely to have the full range, so if there are two or three co-founders, between them they should ideally cover — if not 100%, then at least 70 to 85% — of what I’d expect.

Now, is there a science to that? Of course not. What does 85% really mean? But I’m looking for someone who knows how to sell, someone who knows how to execute, someone with creativity and vision. There are several capabilities I assess. And if those come from working at a large company, that’s perfectly fine.

What do you look for when investing in an early-stage company?

If I’m fortunate enough to be the first check-writer, I invest in the person. The industry, sector, or even technology isn’t the primary factor — it’s the individual. Often, it’s hard for one person alone to build a company. You typically need at least a small team — two people, ideally. In my experience, the chances of success are much higher when there’s that core team in place. But yes, it all starts with the people.

Angel investing is often described as a game of percentages. You’ve been in this space a long time — has anything changed over the years?

Yes, a few things have. Ten years ago, it was easier to get in right at the beginning  — to meet the founder early and write the first check. That came with several advantages: you could invest at a lower valuation and, more importantly, the founders would actually listen to you for the first 12 to 18 months. But once bigger investors come in, that influence starts to fade. You become more of a spectator.

If you’ve built a strong relationship early, your impact during those first crucial months can really help shape the company for the next stages. But that kind of access is harder now. Founders today have more options — there are more angels, more accelerators, incubators — so it’s a lot more competitive.

You’ve mentioned communication and articulation. But beyond that, how can a startup stand out to someone like you, especially with so many vying for attention?

I look for companies that are going against the current. If everyone is pitching AI, AI, AI, and then a retail startup approaches me with a high-volume product, I’ll take that meeting. But I will challenge them: Where exactly is the AI being used? Is it just glorified data processing, with 50,000 rules instead of 500? If you’re doing AI for prediction, is it just correlations and statistics based on past records?

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Some founders can navigate that conversation with clarity; others start to stumble. What I’m really looking for is the ability to back up the claim, whether it’s AI or anything else. That clarity and honesty in articulation are missing in many founders, whether you are in the U.S. or India. It doesn’t matter where you’re from — if you can’t explain it convincingly, that’s a red flag.

Many say non-AI startups are struggling to raise funding because all the money is flowing into AI. Is this a fad?

I think it’s a problem, and it reflects some unhealthy dynamics in the investment world. There’s too much money chasing too few viable opportunities. When that happens, a lot of capital gets deployed lazily, just following trends.

You have private equity firms, hedge funds — groups that traditionally didn’t touch early-stage venture — now allocating small fractions of their massive portfolios to venture capital. Even if it’s just half a percent of their assets, that’s still hundreds of millions of dollars flooding in. But venture investing isn’t just about scale; it’s about precision and risk analysis. And when large funds enter with a portfolio mindset, it can distort the whole market.

So you believe too much good money is being thrown after bad in AI?

Absolutely. About a year ago, I asked someone: Is the energy consumption in AI the same kind of waste as we saw in blockchain? He said yes. With blockchain, the only guaranteed value was the electricity cost. And yet, there was a massive investment.

AI has similar issues. Yes, you get ChatGPT. But think about the energy required for those deep learning cycles. Every time there’s new information or model tuning, it consumes vast electricity. Now, DeepSeek reportedly did similar things with much less energy. That raises questions.

AI has value, but only when it’s highly contextualized. If you’re using it with proprietary data — say, private hospital records — you can actually get very precise, useful insights. But if you’re just scraping public data and running endless neural cycles, the returns are marginal, and the costs are astronomical.

What’s the one piece of advice you find yourself repeating to founders?

I borrow this from the founder of Wendy’s [Dave Thomas], who once said: “To succeed in business, know your product better than anyone else, know your customer, and have a burning desire to succeed.”

Notice he didn’t say “know your customer better than anyone else,” because customers are unpredictable. But if you know your product inside out and are driven to succeed, you have a real shot. That’s where it all starts: know what you’re offering, and know it better than anyone.

What sector or technology excites you right now?

I’m interested in gaming, both for its engagement and its potential. One of my neighbors is working on a great game. Gamification has already transformed sectors like retail. Target was doing it 15 years ago to keep users on their platform longer.

More broadly, I’m drawn to sectors with high volume. That’s where India really shines. I also like “boring” businesses, stuff like database integration, straight-through processing, legacy system optimization. [Microsoft CEO] Satya Nadella said something interesting recently: there’s enough AI out there to last us 10 years. If AI can be used to fix broken systems, that’s where the real value is.

Companies are still using 40-year-old tech stacks with COBOL. The cost to replace them is so high that no one touches them. But if someone can work around those systems and improve them — even marginally — they’ll make money. There’s still a lot of opportunity in fixing the plumbing, so to speak.

You spoke about how even hedge funds are entering the angel investing territory. How has the role of angel investors evolved over the years?

I think it’s evolved in a good way, mainly because there are so many more of them now. This shift is partly due to well-to-do individuals getting bored with their JP Morgan or Morgan Stanley private bankers. The job of those bankers is to collect deposits, place the money, and generate returns that clients wouldn’t otherwise get. But once that kind of investing becomes boring, people look elsewhere. Many of them join angel groups, and there are a lot of those today. In these groups, you’ll find some members who are sharp and really understand the business, and others who are simply there to contribute funds. It’s a mix, but overall, I think it’s a positive development.

You spent decades in finance and worked with some of the largest financial institutions. How did that experience shape your investment philosophy?

It’s interesting. Toward the end of that phase of my career, I started getting bored. I was often involved in regulatory work. You might remember when Sarbanes-Oxley came in, and later Dodd-Frank. I was doing a lot of consulting during that period. But I found it less and less exciting. Luckily, I had a break and got into startups. Once I began seeing some returns, I went full-time into that world.

That shift was partly a reaction to wanting out of the corporate finance world. But it also taught me something important: the timing of when to introduce structure into a startup is critical. You can’t impose rigid procedures too early. By nature, startups need to operate freely. In one case, after about 24 to 30 months, when we’d grown to 30, 40, maybe 50 people, we introduced staff review methods. At that point, you need individual objectives and proper appraisal systems. But when you’re a team of 12 in the first 18 months, who wants to fill out forms?

It’s really about timing, knowing when to implement things like vendor management or contract protocols. You have to temper the natural desire to impose structure too soon.

You were instrumental in the development of a unicorn in India. What’s next for you?

Look, I was lucky to find a couple of really good founders. I did what I could, and they did what they had to do. And now it’s a huge company. But does that mean every other startup I touch will turn into a unicorn? Of course not. I’ve had a few failures, too. I’m hopeful that the medical billing company and the other ventures I’m working with now will get on that same track. But that’s where things stand at the moment.

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