Neil Patel

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Kashish Gupta has already raised tens of millions of dollars for his fast-growing data startup. In fact, they are hiring to keep scaling this year.

On the Dealmakers Show, Kashish Gupta shared his experiences working on both sides of the table, going through pivots, and enjoying inbound pre-emptive rounds from investors. Plus, he provides his unique takes on selling, building a board, and what product-market fit should really look like.

Listen to the full podcast episode and review the transcript here.

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Focus On The Upside

Gupta was born in a small town, a few hours from Delhi, India. Coming from that background he says that you have the mentality that there is really nothing to lose. Any failure has very limited downsides, with great upside potential.

In fact, his top piece of advice when launching a company today is to “go for the upside.”

This is definitely a mindset that he has implemented when creating the board of his startup.

To get that upside he says to be constantly asking what you would have to do to double your growth. If you need to get from $10M to $20M in revenue, think about what it would take to do $40M instead. If you end up hitting $30M, that still beats your initial goal.

Kashish says that he has also chosen to have the mindset that everyone is there to help, if you reach out with a good reason for them to do so, and help them highly leverage their time. That he says has always kept them ahead in terms of new customers and investors. Even before they were ready for them.

When he was six years old his father moved them to the United States to continue his work as an IT consultant with IBM. They continued to move with his work every few months, across many states and cities. It wasn’t until they landed in Atlanta that Gupta says he had some stability through high school.

His dad also owned a gas station. That turned out to be a valuable source of income for putting Kashish through college. Watching his father run that small business showed him how to work hard, and gave him early insights into things like accounting and getting customers.

Starting On The Other Side Of The Table

Kashish went on to study business and computer science at Wharton. He came out of that seeing this combination of being able to both build and sell as having a great advantage over the majority who only learn how to do one of them.

Out of school, he was hired by venture capital firm Bessemer. This was an incredible opportunity to get paid to learn about startup fundraising from the investor side first.

He would spend his days talking to entrepreneurs, exploring their ideas, learning about different industries, and seeing how successful startups are formed and funded.

He says it was a fun ride working with the partners of the firm but didn’t believe he would ever feel fulfilled until he built something of his own.

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Securing Product Market Fit

Kashish Gupta’s first attempt at business was in the travel space. An industry which he now says no one should be trying to get into due to the extremely tiny margins.

Yet, at the time it was compelling. People wanted the product. They said they would pay to use it. In fact, they managed to raise a Seed round of funding and built the company to a few hundred thousand in monthly revenues by early 2020.

At the same time, Kashish saw the problems. People loved it, but they were always looking for the cheapest solution. So, with profit margins under 3%, there just wasn’t a sustainable and profitable business there. Even though many entrepreneurs and investors might have considered them to have found product-market fit.

Kashish began looking for other ways to use his technology outside of the travel space. He struck on data activation. As well as redefining what a good product-market fit should look and work like.

He and his cofounder define product-market fit as being customers onboarding themselves each and every day, without a human helping them. It is automatic inbound product demand. Not just a few large enterprise customers either.

A month later, in February 2020 they found that. It was the trigger to pivot the business to their data activation business.


Hightouch enables its customers to take data from any SaaS tool, and sync it. With the goal of having more actionable data available to every person on the team.

They’ve now raised $54M for Hightouch, and have been using that to scale.

Storytelling is everything which is something that Kashish Gupta was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

They grew from 4 to 40 people. Then in the first half of 2022, they grew from 40 to 90 employees. Kashish says that their customer growth has mimicked that as well. Going from just 4 customers at the start of 2021, to 200 by the end of that year. Now at around 300, they expect to be on track to 500 customers by the end of 2022. Pretty mature and large corporate customers as well.

This growth has helped Hightouch continually attract inbound investor interest. Meaning they’ve received preemptive investment offers before needing the capital at each round.

This often happens with investors seeing the advantage of beating out their competition as great opportunities. In exchange, they may invest a year ahead of the startup’s need, and still, give them the valuation they would have gotten if they waited.

Listen in to the full podcast episode to find out more, including:

  • Building the right board dynamics
  • The future of data activation
  • A different approach to selling customers


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Neil Patel

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