He Cofounded A $100 Million AUM Hedge Fund And Has Now Raised $50 Million To Build A Diversified Immersive Technology Platform

Lyron Bentovim’s entrepreneurial career is anything but linear. His journey spans continents, cycles, and sectors. He started as an ice cream shop operator in Israel, a tech entrepreneur in the dot-com era, a hedge fund manager during the bust, and became a public company turnaround executive.

Lyron is now the founder of a publicly traded immersive-tech platform. His story isn’t merely about navigating ups and downs; it’s about applying lessons across industries, leveraging timing, and learning to build companies differently at different stages of life.

This is the business and life philosophy behind Glimpse, a trailblazing platform that Lyron has been building for nearly a decade. In an interview on the Dealmakers Podcast, he talks about his experiences getting companies off the ground, raising funding, and taking them public.

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

Born in Startup Nation, Raised With Risk in His Blood

Growing up in Israel, entrepreneurship isn’t a career choice; it’s cultural DNA. “Starting things and taking risks is part of the environment,” Lyron said. “That mindset has driven everything I’ve done.” Moving later to the UK and then the U.S. expanded that outlook.

Experiencing business environments across multiple countries helped Lyron see problems and gain perspectives from “the outside” and from different angles. That, in his opinion, makes a huge difference. He also developed flexibility and tolerance for change and moving around.

Lyron learned not to be afraid of taking risks and to be open to doing things differently. These lessons enabled him to be successful wherever he went.

The First Company: An Ice Cream Shop That Became a Masterclass

Lyron’s first company was in the food space. He and a friend acquired a mediocre ice cream shop in a great location. The duo saw that the place had great potential, so they redesigned it, revamped the menu, and repositioned it. And it flourished.

The original owners had a factory where they manufactured the ice cream and continued supplying it for sale in the store. But what mattered wasn’t the profit. It was the education. Lyron learned valuable lessons in how a business works and in balancing payables and receivables.

He also learned to acquire and manage customers, and gained other insights that he would later translate into corporate leadership, venture building, and IPO navigation. He eventually sold his share to his cofounder, learning when to turn the page; a lesson he revisited twice during his career.

Starting Young vs. Starting Mature: Two Different Games

Lyron has built companies both as a young founder and as a seasoned operator. He sees the distinction clearly, saying, “When you’re young, you run on energy and enthusiasm.” The lack of experience with the world prompts you to push forward at an entirely different pace.

In your 40s or 50s, maturity makes you respond to setbacks analytically rather than emotionally. You view obstacles as hurdles to navigate, not life-altering catastrophes. Thought processes change, and the word “no” triggers the willingness to pivot and work around it.

In Lyron’s opinion, younger founders are more determined to follow their dreams and build on them. They lack the willingness and ability to view the dream through a different lens. Thus, they are not willing to pivot and align their vision with what the audience is telling them.

Maturity brings flexibility and creativity in resolving challenges. Lyron is now not afraid to dive into the unknown and try something different when needed. Looking back, he talks about moving to the US to pursue an MBA at Yale.

As Lyron views immigrants, they have one of two philosophies. One–they stay within their community and continue living with their people. He chose the second path — to keep his identity within himself while also connecting with and embracing the land of opportunity.

Tech Cycles Never Die; They Evolve

After Yale, Lyron founded WebBrix, that startup that enabled him to experience the complete company cycle, including, in this case, the dot-com bust. His take on tech cycles is unusually structured. He says, “Technology cycles are 30 to 35 years.”

The digital cycle began in the early 1980s, surged with the internet boom, crashed in 2000, and matured around 2015. Lyron recalls his first exposure to technology in the 80s, when he saw an ad for the ZX81, one of the first computers with 1K of memory.

By the time Lyron successfully convinced his parents to buy one for him, 12 months had passed, and he purchased an advanced version of the computer. In retrospect, he considers the dot-com bust to be the two-thirds point of the tech cycle.

The Dot-Com Bust and Lessons Learned

As Lyron points out, crashes are not the end; they’re a midpoint, and the companies that endure them (Amazon being the best case study) become giants. This leads to the most expensive lesson Lyron learned at WebBrix: “Never say no to capital when it’s available.”

At the height of the internet boom, Lyron turned down money at a $10M valuation. Months later, when the crash came, capital evaporated. The markets crashed, and people didn’t want to touch the internet, even though it wasn’t the end of the cycle, merely a blip.

Lyron’s takeaways from the experience.

1. Don’t view hurdles and setbacks as the end of the world, but as a part of the cycle.
2. Focus on surviving the setback and position yourself for further success as the cycle progresses.

Leveraging the Advantage of Switching Between Industries

Asked whether switching industries gives one an advantage, Lyron considers it a significant edge. The switch enables knowledge transfer, he says. He was able to apply some of the lessons he learned to a different segment he wanted to tackle, much like Elon Musk’s switch from payments to cars.

Similarly, Lyron successfully jumped from food to the web, to hedge funds, and then back to tech and the VR space. The ability to innovate within different environments, take the lessons learned, and apply them to other sectors was a considerable advantage.

Lyron views everything he does as a learning experience. He dives into a new industry without hesitation, understanding the need to get up to speed quickly. When he started Glimpse, he concedes he knew nothing about the virtual reality space, but now he knows as much as anyone in it.

As Lyron points out, entrepreneurs should not restrict themselves to their comfort zones in terms of technology or industry. Instead, they should expand their horizons and explore different pathways.

Reinvention: From Dot-Com Meltdown to Hedge Fund Innovator

After unwinding WebBrix, Lyron found himself surrounded by bankrupt startup shells with valuable IP. He himself carried around boxes of his company’s materials, hoping to resuscitate it at some point. This was before everything became digital.

Lyron tried to stitch together the technologies of broken companies into something new, but private markets were impossible because investors wouldn’t let go of “dead” assets. They were looking for high returns to recover some of their losses.

So in 2001, Lyron pivoted toward public markets. He was introduced to Russell Silvestri, who became his partner in starting Skiritai Capital. At the time, 550 technology companies within 100 miles of San Francisco were trading below cash value, though they had the technology, business, and other assets.

Lyron and his partner got in a car and physically visited companies. They spent time meeting with the management and invested in them to help position them for success. The duo recognized the once-in-a-lifetime opportunity and went on to build a successful hedge fund.

Lyron leveraged lessons learned from building his startup, which included understanding technology, management consulting, and working with C-level executives in large companies.

The Itch to Operate: Leaving the Fund to Fix Companies

Investing wasn’t enough. Lyron wanted to start a new chapter. He wanted to build and execute. By this time, he had around $100M in assets under management (AUM). As the fund evolved, Lyron started taking on more of an operating partner role.

Although Lyron continued working with the investments and their management teams, he took on a more advisory role or served as a board member. He stepped in to turn around public companies like Sunrise Telecom and Top Image, after selling his stake to his partner.

The lesson from turnarounds? As Lyron says, “Until you understand the real problem, you haven’t done enough research.” Turnarounds fail when leaders chase symptoms instead of root causes, which could be issues with the business, customer fit, product, or cash flow.

Lyron would work with his analysts, who were analyzing companies with poorly-performing stock. As the investor, he would ask questions like: “Does the management know how to solve the problem?” But when he turned it around, he would ask: “How to address the problem?”

Lyron’s experience sharpened the diagnostic instincts that later helped him build Glimpse.

The Birth of Glimpse: Timing Meets Pattern Recognition

Having completed his roles at Sunrise Telecom and Top Image, Lyron was ready for the next phase of his career. Immersive tech (VR, AR, AI, blockchain) had been around since the 1990s, but it only became commercially viable in 2015.

When Lyron started researching, he realized he could get into the tech cycle early. This was unlike his previous experience with WebBrix, when he had entered the sector at its midpoint. This time, he wanted to be there from the beginning, not chasing from behind.

Lyron recognized early that virtual reality (VR), augmented reality (AR), artificial intelligence (AI), and blockchain would form an immersive world. It was the next transition from a digital world at the end of the previous tech cycle. This was the opportune time to leverage all the lessons he had learned.

A serendipitous search for “NYVR” led him to DJ Smith, his future co-founder, just one hour before DJ’s meetup. The timing was interesting, as the duo would meet on the last or third Thursday at 6:00 pm in Manhattan.

They met for lunch, and walking toward the restaurant, the Glimpse model came to Lyron in a flash: Roll up best-of-breed VR/AR startups under a unified platform. That idea became Glimpse Group.

At the time, DJ was running the largest meetup in the city for immersive technologies, which was also the second largest in the world. He was connected to several startups in the scene and began bringing them in to evaluate their fit and interest in collaborating.

Simultaneously, Lyron and DJ worked to secure seed funding to launch the company.

Glimpse: The Platform Approach to Immersive Tech

Explaining the Glimpse business model, Lyron reveals that it is essentially a software platform that brings together multiple “best of breed” software companies selling immersive technologies to enterprise customers.

Glimpse sells software solutions in a variety of areas to the military, defense, marketing, healthcare, and education sectors. Although the different companies focus on various industries and offer diverse technologies, they are wholly owned by Glimpse and managed and operated by it.

Each subsidiary has autonomy and its own general manager (GM), but Glimpse provides scale, credibility, shared infrastructure, and market access. It isn’t a siloed startup; it’s an ecosystem.

Raising Money Without VC: A Very Conscious Decision

Lyron raised $50M in capital, but not through venture capital. He believes traditional venture capital (VC) incentives and founder incentives are misaligned, especially for companies aiming to go public.

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

Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.

Lyron had a vision that Glimpse would go public eventually. Thus, he focused on nigh-net-worth individuals and family offices, raising small rounds by carefully vetting their investors. They “kissed a lot of frogs” and found the right long-term partners.

Lyron strongly believed that “You don’t raise money when you need it. You raise the money when there is enough interest in your company that would make raising money viable.” He sees it as a totally different skill set and art than raising money for a private company. He learned how to do both.

Going Public: Prepared Years Before It Was Possible

From Day 1, Glimpse was structured to become a public company. Lyron and his cofounders conducted audits while doing just $70K in revenue their first year. That looked crazy until 2021, when the capital markets for immersive tech opened.

Because they were ready, the IPO happened rapidly. “Within six months, we were public on NASDAQ,” Lyron recalls. It was a regular IPO, not a SPAC, not a reverse merger. This was a rare move for such an early company.

As Lyron says, you need to learn to navigate all the pros and cons of situations. Their pro was that they could increase the valuation without any effort. He recalls the time when Facebook rebranded to Meta. Investors wanted pure-play metaverse stocks.

But Glimpse was the only one. When its stock jumped 50% in a single day, Lyron acted instantly. He phoned his bankers at 2:00 pm, negotiated overnight, and by morning, they had $15M more in the bank. That’s what timing and preparedness look like when public markets get excited.

The Future Immersive World and Advice to Founders

In Lyron’s future is a world where we do everything digitally. Zoom calls become immersive virtual offices, support groups meet in virtual shared spaces, and virtual tourism becomes mainstream. That’s just for starters.

Lyron’s message to his younger self? “Don’t give up. Every obstacle is solvable if you stay creative.” Just assume that every kind of challenge you see is an obstacle to overcome.

Listen to the full podcast episode to know more, including:

• Lyron sees entrepreneurship as cultural DNA, leveraging global perspective and risk-taking instincts to build across industries.
• Early failures taught him a core rule: never say no to capital when it’s available because timing is everything.
• He views tech cycles as lasting 30 to 35 years, and mid-cycle survival creates the giants who shape the future.
• Switching sectors created unfair advantages by transferring insights across food, web, hedge funds, turnarounds, and immersive tech.
• He structured Glimpse as an ecosystem of VR/AR companies, proving the power of a platform over siloed startups.
• Avoiding VC funding allowed alignment with public-company incentives and enabled a rapid, clean IPO.
• Preparedness and decisive action—years before needed—let Glimpse seize market timing, raise capital, and lead the immersive-tech cycle.

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Keep in mind that storytelling is everything in fundraising. In this regard, for a winning pitch deck to help you, take a look at the template created by Peter Thiel, the Silicon Valley legend (see it here), which I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash. 

Remember to unlock for free the pitch deck template that founders worldwide are using to raise millions below.

 

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