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Darshan Somashekar

Product/tech founder | Sold ed-tech company for $60M | Building a multi-million dollar gaming startup | Upgrading your brain through gaming

Professional Background

Darshan Somashekar is a multi-talented professional with extensive experience in technology, business, and product management. As a tech co-founder, investor, and management consultant, Darshan has cultivated a diverse skill set that positions him as a thought leader in the entrepreneurial space. With a proven track record of success, he has contributed to the development and growth of several startups, making substantial impacts in the tech landscape.

One of Darshan's notable achievements includes co-founding drop.io, a pioneering media sharing platform that quickly gained traction and received venture capital backing, ultimately being acquired by Facebook in 2010. This acquisition set the stage for Darshan's subsequent entrepreneurial endeavors, showcasing his ability to innovate and create value in the tech sector.

Following drop.io, he co-founded Imagine Easy Solutions, which focused on creating research and citation tools under its flagship product, EasyBib. This venture also garnered significant attention and was acquired by Chegg in 2016, further solidifying Darshan's reputation as a leading figure in tech entrepreneurship. After the acquisition, he played a pivotal role at Chegg as the VP of Product for its newly formed Writing Tools group, where he leveraged his insights and leadership skills to drive product innovation and enhance user experiences.

In addition to his entrepreneurial ventures, Darshan has served as a Venture Partner at TMV, a New York-based seed-stage venture capital fund. His role there involved mentoring and guiding emerging startups, sharing his wealth of knowledge and experience to help other founders navigate the challenges of building successful companies. Currently, Darshan is focusing on his latest startup, Solitaired, where he continues to explore new frontiers in the tech industry and create engaging products that resonate with users.

With a well-rounded background in various aspects of business and technology, including programming and product development, Darshan Somashekar is a dynamic force in the entrepreneurial landscape, consistently seeking out innovative solutions that meet the needs of today's consumers.

Education and Achievements

Darshan Somashekar graduated from Brown University with a Bachelor of Arts in Public Policy and American Institutions. His educational background is integral to his approach to business, as it has provided him with a strong foundation in critical thinking, analysis, and understanding the societal implications of technology and business decisions.

Before entering the entrepreneurial landscape, Darshan honed his skills as an Associate Consultant at Bain & Company in New York. This experience allowed him to immerse himself in various industries, collaborate with clients on strategic initiatives, and develop robust problem-solving abilities. The insights gained during his tenure at Bain have undoubtedly informed his approach to product management and venture capital, allowing him to evaluate opportunities from multiple perspectives.

In addition to his professional achievements, Darshan's involvement with various organizations, including his previous positions at Unwind Media and Sota Partners, has enriched his expertise in strategic planning and execution. By participating in diverse projects, he has built a vast network of industry contacts and gained invaluable insights into emerging trends and technologies.

Notable Achievements

  1. Co-Founder of Drop.io: Darshan was instrumental in the founding of drop.io, a media sharing platform that gained significant traction and was ultimately acquired by Facebook, highlighting his capability to build and scale successful tech startups.
  2. Co-Founder of Imagine Easy Solutions: Under his leadership, this venture created EasyBib, a widely-used research and citation tool, further solidifying his impact on educational technology. The company was acquired by Chegg, allowing for continued growth and expansion of its offerings.
  3. VP of Product at Chegg: Darshan took on a significant leadership role at Chegg, overseeing the Writing Tools group and spearheading innovative solutions that benefited students and educators alike.
  4. Venture Partner at TMV: His role as a Venture Partner allowed him to support and mentor emerging startups, sharing his wealth of experience and providing guidance on product development and business strategy.
  5. Founder of Solitaired: Darshan's latest entrepreneurial venture, Solitaired, showcases his continued passion for technology and innovation as he explores new product ideas and collaborations.

In conclusion, Darshan Somashekar's impressive background, marked by significant achievements in technology and business, underscores his position as a leading entrepreneur and thought leader. His commitment to innovation, coupled with his extensive experience in product development and venture capital, continue to

Highlights

Aug 13 · linkedin

Your life expectancy is 77.

But by 2050, you'll work until you're 70 (according to the World Economic Forum).

Here's why your kids won't know what "retirement" means:

The math of retirement is broken.

In 1960, there were 5.1 workers for every retiree.

Today? Just 2.8.

Here's where it gets wild:

Social Security's trust funds will be depleted by 2034.

After that, it'll only be able to pay 78% of scheduled benefits.

That's like planning a 30-year retirement and running out of money after 23 years.

Let's rewind to 1900:

The average American lived to 47.

If you made it to retirement age, you'd be lucky to enjoy a few golden years.

Fast forward to 2019, and we're living to 77+ on average.

That's great news, right? — Well, not for our retirement systems...

Our systems weren't built for this longevity boom.

In just 23 years, the number of Social Security beneficiaries has exploded:

• 2000: 45 million • 2023: 70 million

That's a 55% increase. And this isn't just a U.S. problem:

Japan, the world's "oldest" country, is facing a similar crisis:

• 29.1% of population is 65+ (as of 2021) • 1 in 4 elderly Japanese still work past 65 • Pension age: increasing from 65 to 70 by 2025

They're pioneers in the "never-ending work life" experiment.

Back in the US, the "real" retirement age is already creeping up:

In 1991, 11% of Americans aged 65+ were working.

By 2022, that number rose to 19%.

People are adapting, but it's not all smooth sailing...

Increasing retirement age hits some harder than others:

• Blue-collar workers often can't work as long • Lower-income Americans have shorter life expectancies

A 2017 GAO study found the poorest men live 11.9 years post-65, while the richest live 16.2 years.

This disparity makes a one-size-fits-all retirement age problematic.

Some are rethinking retirement altogether.

Warren Buffett, still working in his 90s, says:

"If you like what you're doing, if you feel useful, why in the world should you retire?"

But not everyone has that luxury or desire.

Some companies are adapting to an aging workforce. Take BMW:

They created a "pensioner's assembly line" with wooden floors, adjustable workbenches, and ergonomic chairs.

Result? 7% productivity boost, matching younger teams.

What can you do to prepare?

• Open a Roth IRA: $6,500 limit (2023) • Max out 401(k): $22,500 if under 50 (2023) • Invest in health: $1 on wellness can save $3.27 in medical costs

Consult a financial advisor for the above. But here's what I do recommend:

Find Work You Love

It might keep you engaged well past the traditional retirement age.

Staying active & learning new skills are your best bets to stay happy & financially secure.

The future might be "work differently" rather than "don't work at all."

A bit about me:

I built an ed-tech business as a high schooler, grew it to 30M users, and sold it to Chegg for $60M.

Now, I'm building a multi-million dollar casual gaming startup with only 5 people.

Jul 30 · linkedin

1 in 7 adults is a millionaire in Switzerland. That's 5x higher than the US.

I had to find out their wealth-building habits...

7 ways the Swiss think about money to become richer than you:

Switzerland has the world's largest percentage of millionaires.

AND they have 1 billionaire for every 80,000 people.

Before we dive in, here's the low-down:

• 14.9% of Swiss adults are millionaires • That's nearly double the rate of the US (8.8%) • Yet Switzerland isn't even in the top 10 for average income

So how do they do it?

It's all about some key mindset shifts.

  1. They Rent for Life (& They Love It)

Shocking fact: Only 41% of Swiss own their homes.

In the US? It's 65%.

Swiss millennials aren't obsessed with buying houses.

Why? They invest the difference in high-yield assets instead. Meanwhile...

  1. They Treat Saving Like a Bill

Most people save what's left after spending. The Swiss? They spend what's left after saving.

They automate 20-30% of their income into savings BEFORE touching it.

It's not about willpower. It's about systems.

  1. Swiss People Invest in Themselves

The average Swiss spends 5-10% of their income on education and skills.

Every year. They're not chasing degrees. They're after specific, high-value skills.

Think languages, tech skills & financial literacy.

  1. The "Multi-Bank Strategy"

Swiss millionaires don't put all their eggs in one basket.

They typically use 3-5 different banks for various purposes:

• Local bank for daily transactions • Private bank for wealth management • International bank for foreign exchange

Why do this?

  1. Risk Mitigation & Opportunity Maximization

Different banks = different strengths and offerings.

For example, one might offer better rates for real estate investments, while another excels in international trades.

It's about leveraging each bank's unique advantages.

  1. Master "Stealth Wealth"

You won't see Swiss millionaires flaunting designer logos or exotic cars.

They live below their means and reinvest the difference.

It's not about deprivation. It's about delayed gratification.

  1. The "Global Citizen" Approach

Swiss investors think beyond borders.

They diversify globally, not just in assets, but in residency and citizenship.

Many have second passports or residencies in other countries because it opens more financial opportunities & tax optimizations.

These strategies require patience and a long-term mindset.

True wealth isn't about making money. It's about keeping and growing it.

So, what can we learn from the Swiss millionaire mindset?

• Automate your savings • Live below your means • Invest in high-value skills • Think long-term and globally • Diversify across banks and borders

The path to wealth is a marathon. Are you ready to run it?

A bit about me:

Since selling my ed-tech company for $60M, I’ve been building a casual gaming startup with just 5 people.

Check out Solitaire (to maximize your brain health):

https://solitaired.com

Related Questions

How did Darshan Somashekar navigate the challenges of co-founding multiple successful startups?
In what ways did Darshan's experience at Bain & Company shape his approach to product management?
What inspired Darshan Somashekar to launch his latest venture, Solitaired?
How has Darshan applied his degree in Public Policy to his various roles in technology and entrepreneurship?
What insights can Darshan Somashekar share with aspiring entrepreneurs looking to enter the tech industry?
Darshan Somashekar
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New York, New York, United States