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The Secret Weapon for Scaling & Selling Your Business—Most Founders Overlook This!
What you missed on How2Exit This week
Ronald Skelton
April 01, 2025
Sponsors:
DueDilio is your go-to marketplace and advisory service for all things related to small business acquisitions.
and
Final Ascent, a premier boutique professional services firm specializing in mergers and acquisitions, exit strategies, and growth consulting tailored for lower middle-market firms across the U.S.
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E274: The Secret Weapon for Scaling & Selling Your Business—Most Founders Overlook This!
About the Guest:
Ashish Gupta is the founder of Scale Up Exec, a firm specializing in fractional COO services for growing businesses. With a background in tech startups, corporate leadership at Apple, and turnaround management in the e-commerce space, Gupta has a proven track record of scaling companies and preparing them for exits. His approach blends operational efficiency, strategic growth, and leadership coaching to help founders achieve their business goals.
Summary:
In this episode of the How2Exit Podcast, host Ronald Skelton sits down with Ashish Gupta, founder of Scale Up Exec, a fractional COO firm that helps small and mid-sized businesses scale, streamline operations, and prepare for exits. Gupta’s experience spans from founding a wireless startup acquired by Qualcomm to managing billion-dollar budgets at Apple, to turning around distressed e-commerce businesses and advising companies on high-impact growth strategies. The conversation dives deep into the role of a COO, how founders can recognize when they need operational support, and what it takes to transition from a hands-on entrepreneur to an owner ready for an exit.
This episode is a must-listen for business owners struggling with growth plateaus, operational inefficiencies, or founder burnout. Gupta provides an eye-opening perspective on how businesses should think about leadership transitions, succession planning, and the strategic use of fractional executives to achieve scalable success.
Key Takeaways:
The Invisible COO Role in Small Businesses – Even if a company doesn’t have a formal COO, someone is always filling the operational leadership role, whether it’s the founder or an informal manager.
Why Founders Get Stuck – Most entrepreneurs are either visionaries or execution-focused, but rarely both. Without a strong operations leader, founders can get caught in a cycle of inefficiency, distraction, and burnout.
Recognizing Exit Readiness – Not all business exits are the same. Some founders just want to step back from day-to-day operations, while others need a full buyout. Knowing the difference is crucial for structuring the right transition.
Strategic vs. Financial Buyers – A company’s value depends on who the buyer is. Strategic buyers may care more about market share or IP, while private equity and individual buyers are EBITDA-focused. The key is optimizing the right metrics.
Boredom is a Business Killer – Many founders unconsciously sabotage their businesses because they get bored after a few years. This often leads to side projects, disengagement, or operational neglect.
Fractional COOs as a Scalable Solution – Many companies under $10 million in revenue can’t justify a full-time COO, but a fractional executive can provide high-level leadership and operational improvements without the full-time cost.
The Power of Small Changes – Business turnarounds don’t always require sweeping changes. Gupta advocates for a step-by-step approach to transition founders out of operations, proving that small wins build trust and momentum.
AI’s Emerging Role in Operations – While AI is improving efficiency in operational management, it still lacks the human touch necessary to navigate company culture, team motivation, and complex decision-making.
Attention Business Brokers, Advisors, Acquisition Entrepreneurs, and SMB Owners!
Do you want to stay ahead of the game in the SMB M&A market? The Hub is the solution you need! This curated newsletter brings you the best highlights from blogs, podcasts, YouTube, and news sources, all in one place. Growth & Acquisitions
Founding Member Shout-Out (Still room here -$400 one time)
Shout out to our new founding member. With over 30 years in M&A, this company offers the lowest priced (way undervalued) course on helping you buy good businesses. Very underpriced - get it now before they finish upgrading the site and very likely up the pricing.
