Avoid Major Scaling Mistakes with Robert Levin

In this episode of the DealQuest Podcast, I’m thrilled to welcome Robert Levin, a serial entrepreneur and seasoned investor with a track record of building and successfully exiting multiple companies. With experience deploying over $300 million across more than 20 deals, Robert brings a wealth of knowledge about scaling businesses, navigating investment opportunities, and achieving high-value exits.

From his early days as a Navy veteran to earning his MBA at Harvard Business School and becoming a respected leader in the investment community, Robert shares actionable insights on what it takes to grow and sell a business successfully. In this conversation, we explore the key strategies behind scaling, the nuances of investment decision-making, and the lessons learned from leading multiple companies through IPOs. Let’s dive in!

SUCCESSFUL BUSINESSES SOLVE PROBLEMS PEOPLE WILL PAY FOR

Robert Levin became an “accidental entrepreneur” when a simple project unexpectedly turned into a thriving business. A company needed a specific service, and he took on the challenge without intending to start a business. But as demand grew, he hired employees, rented office space, and soon found himself leading a company that was eventually acquired.

Successful businesses solve real problems—but not all problems make good business opportunities. Many entrepreneurs waste time chasing ideas that seem innovative but don’t address a pressing need people are willing to pay for. Levin emphasizes the importance of asking two crucial questions: Does this problem truly need solving? And will customers eagerly pay for a solution? If the answer isn’t clear, it’s a red flag. His experience proves that finding the right problem with real demand is the foundation of every successful venture.

EXECUTION MATTERS MORE THAN IDEAS

Many entrepreneurs assume that having the best technology or most advanced product guarantees success. But Robert Levin warns that execution—not just innovation—determines whether a business thrives.

Early in his career as an equity analyst, Levin saw the intense preparation behind a major insurance company’s IPO, from financial structuring to market positioning. Later, when launching his own businesses, he realized that having a great idea was just the beginning—building a team, attracting customers, and scaling the business were the real challenges.

A common mistake he sees is entrepreneurs obsessing over their product without validating whether people actually want it. Even the best technology will fail if no one is interested. Levin’s success in building and selling companies—including ones that went public—came from ensuring his ideas were backed by demand and executed effectively. The takeaway? A great business isn’t just about innovation—it’s about execution.

BIG MONEY LIES IN FIXING WHAT BUSINESSES OVERLOOK

Robert Levin’s success came from identifying expensive inefficiencies that companies didn’t even realize were problems. In the 1990s, large pharmaceutical firms were acquiring biotech companies to expand their R&D pipelines. But along with new drug developments, they also inherited pension plans, insurance policies, and benefit structures they had no idea how to manage. Instead of reassessing these obligations, they continued paying millions annually without question.

Levin saw an opportunity. His company helped pharmaceutical firms analyze these financial burdens, determining which were necessary, which could be optimized, and which could be eliminated—ultimately saving them millions. His key lesson? The best business opportunities often lie in solving costly, overlooked problems that companies don’t have the time or expertise to address.

SMALL DETAILS CAN LEAD TO BIG OPPORTUNITIES

Levin’s ability to spot hidden financial inefficiencies didn’t just help companies cut costs—it created unexpected windfalls. While working with a private equity firm acquiring a distressed manufacturing business, his team examined the company’s pension plan. Investors assumed it was a financial liability, but Levin discovered it was actually overfunded by $15 million. This insight instantly turned what seemed like a burden into a major asset.

By uncovering overlooked value, Levin’s firm became a highly sought-after partner, leading to more deals where similar hidden opportunities were found. The key takeaway? Success in business isn’t just about having a great idea—it’s about execution, looking beyond the obvious, and asking the right questions. Sometimes, the biggest wins come from finding value in places others ignore.

RAISING CAPITAL CAN COST YOU CONTROL

Many entrepreneurs see outside investment as the key to scaling their business, but few realize the trade-off—losing control.

Robert Levin shares a cautionary tale of a founder who took funding from a private equity (PE) firm, only to watch his vision sidelined. The PE firm installed a board member whose priority was preparing the company for sale—whether the founder agreed or not. With investors holding decision-making power, the founder lost control of his own company’s future.

The lesson? Investors have their own agendas, which may not align with yours. Before seeking funding, consider whether the benefits outweigh the loss of autonomy. Sometimes, slower, self-funded growth is the better path.

FOLLOW THE HERD CAN LEAD TO REGRET

Many entrepreneurs feel pressured to follow industry trends—whether it’s securing venture capital, pursuing rapid growth, or selling their business for a big exit. Robert Levin warns that simply copying what others are doing doesn’t guarantee success. In fact, it can lead to regret if founders don’t fully consider what they truly want.

He shares a story about a business owner who sold his company, only to realize afterward that his life hadn’t actually improved. The money from the sale didn’t significantly change his lifestyle—he was already making $3 million a year, more than enough to afford anything he wanted.

But after selling, he found himself feeling lost. He had spent decades running his business, and without it, he wasn’t sure what to do next. This highlights an important point: just because selling seems like the "next step" doesn’t mean it’s the right one. Entrepreneurs should ask themselves whether they are making decisions based on external pressures or their own true goals.

MAKE BUSINESS DECISIONS WITH CLARITY

Founders often rush into selling, raising capital, or scaling without fully considering their long-term goals. Levin warns that many assume they’ll sell and start another business—but if that’s the plan, why sell at all?

He shares the story of a founder who took $100 million from Apollo, expecting it to be transformative. Instead, it came with constant investor oversight, pressure for rapid growth, and a loss of control. What seemed like a great move ended up restricting the founder’s freedom.

Entrepreneurs should ask: Is this decision truly improving my life, or am I doing it because I think I should? Clarity and intention in decision-making can prevent regrets and ensure a business aligns with personal goals.


ENTREPRENEURSHIP HAS HIGHS AND LOWS—KEEP GOING

Success doesn’t mean the road is easy. Even accomplished entrepreneurs face challenges, like running low on cash and scrambling for funding. Robert’s friend built a scalable business but repeatedly found himself needing to pitch investors just to keep things running.

Each time, he dealt with the emotional rollercoaster of uncertainty, questioning whether the business would survive. This cycle isn’t unique—it’s part of the entrepreneurial journey. No founder has a story without struggles. The key difference between those who succeed and those who don’t is their ability to push through setbacks, adapt, and keep moving forward.

ALWAYS DO YOUR DUE DILIGENCE—REPUTATION ISN’T ENOUGH

Big-name companies may seem trustworthy, but history proves that even the most established firms can hide serious financial and legal issues. Years ago, private companies often dismissed transparency requests with, “We’re [Company X], what are you worried about?”—as if their reputation alone was proof of integrity.

Then came the Enron and WorldCom scandals, exposing massive fraud and costing investors billions. These disasters forced the business world to recognize the importance of reverse due diligence—thoroughly vetting not just the companies you acquire but also those acquiring you.

No matter how well-regarded a business appears, never assume it’s financially sound. Always verify the numbers, dig deep, and ask tough questions. Skipping due diligence can lead to devastating losses, even when dealing with industry giants.


SCALING ISN’T JUST REVENUE—GET THE RIGHT SUPPORT

Growing from a startup to a mid-sized business ($10M–$100M in revenue) presents a unique challenge. Startups have access to accelerators and VC funding, while major corporations can turn to top consulting firms. But mid-sized companies? They’re often left navigating growth, acquisitions, and capital raises on their own.

Robert Levin saw this gap firsthand—many founders relied on peer support, which led to venting rather than solutions. That’s why he launched his firm, offering strategic and M&A advisory services to help these businesses scale successfully.

The takeaway? Scaling isn’t just about revenue—it’s about securing expert guidance. Without it, mid-sized businesses risk stagnation, bad deals, or selling for far less than they’re worth.


Tune in to this episode to hear Robert Levin share his insights on scaling businesses, executing ideas effectively, and navigating investment decisions for long-term success.

• • •
Listen to the Full DealQuest Podcast Episode Here
• • •

FOR MORE ON ROBERT LEVIN

Robert Levin’s LinkedIn
CIS Ventures, LLC

FOR MORE ON COREY KUPFER

Corey Kupfer's LinkedIn
Corey Kupfer's Website

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!