What if buying a business with zero industry experience meant stepping right onto the brink of bankruptcy?

Our guest today bought a failing HVAC company generating two million dollars in declining revenue, only to discover it was losing money on almost every job.

Instead of chasing more leads or lowering prices, he made a few bold bets that would outperform any marketing or technology. That strategy didn't just save the company—it grew it from under one and a half million to over ten million dollars with a team that now runs the business without him.

Welcome to today’s episode of Your Business Growth Podcast. I’m your host, Jeremy Shapiro, author of Your Business Growth Playbook, and my guest today is Rich Ashton!

He gained 4,000 paying customers. Then hundreds demanded their money back—and Stripe temporarily shut down his payment processing.

What looked like a breakthrough for Dmitry Dragilev's SaaS startup almost destroyed the company.

In this episode of Your Business Growth Podcast, Jeremy Shapiro interviews Dmitry Dragilev, founder of JustReachOut, about his 4x exits, the promotion that nearly ended his business—and the shift that led to a near-million-dollar exit.

Dmitry had built a PR software platform that helped entrepreneurs connect with journalists. An AppSumo partnership brought thousands of new customers and an immediate surge in revenue.
But many buyers expected lifetime access.

When renewal charges started appearing a year later, hundreds of customers disputed their payments. Stripe temporarily suspended processing, the team stopped shipping new features, and Dmitry spent months managing refunds and customer complaints.

The solution wasn't another software feature.

Dmitry discovered that many customers weren't using the platform because they didn't know how to pitch journalists. They needed someone to help them do the work.

He introduced PR coaching and white-glove services, helping the business reach $50,000 in monthly revenue, lower churn from approximately 30% to 7–10%, and eventually sell for just under $1 million.

In this episode, we discuss:
✔️ The AppSumo deal that attracted 4,000 customers
✔️ Why lifetime-deal expectations caused a chargeback crisis
✔️ How Stripe's payment suspension threatened the business
✔️ The hidden costs of rapid SaaS customer growth
✔️ Why customers weren't using the product they purchased
✔️ Adding premium services to a software business
✔️ How monthly revenue stabilized around $50,000
✔️ Reducing customer churn from 30% to 7–10%
✔️ What buyers look for when acquiring a business
✔️ Building and selling four companies
✔️ Using established marketplaces to acquire customers
✔️ Creating businesses around a three-hour workday

Dmitry also explains why he thinks about potential acquirers before launching a business, why he prefers bootstrapping, and how delegating operations helps him spend more time with his family.

If you're building a SaaS startup, struggling with customer retention, or thinking about selling your business, this conversation offers practical lessons on pricing, cash flow, customer needs, and building a company buyers want.

👉 Connect with Dmitry Dragilev:
• Website: https://criminallyprolific.com/
• Dmitry on LinkedIn: https://www.linkedin.com/in/dmitrydragilev/

📘 Hosted by: Jeremy B. Shapiro, Host and Author, Your Business Growth Playbook (https://yourbusinessgrowthplaybook.com/)

Chapters:
00:00 Deal Gone Wrong
01:21 From Polls to Google
02:28 Newsjacking for Traffic
05:38 Growth Without Revenue
06:43 Building JustReachOut
08:52 Bootstrapped SaaS Surge
10:41 AppSumo Lifetime Trap
20:05 Renewals and Chargebacks
25:09 Surviving Stripe Shutdown
28:21 Support Chaos and Recovery
30:56 SaaS Plateau Reality Check
32:17 PR Coaching to White Glove
33:59 Balancing SaaS and Services
36:04 Three Hour Workday Ops
39:15 Equity Partner Pitfalls
44:08 Services Boost Exit Value
46:38 Lean Build to Sell Playbook
48:59 New Ventures Distribution Hacks
52:19 Fixing Broken Business Models
54:36 Rapid Fire and Wrap Up

Keywords: Dmitry Dragilev, JustReachOut, SaaS business, SaaS startup, SaaS growth, business exit, selling a business, million dollar exit, AppSumo, AppSumo lifetime deal, Stripe chargebacks, payment processing, startup failure, business turnaround, SaaS churn, customer retention, recurring revenue, bootstrapped startup, business model pivot, white glove services, three hour workday, Jeremy Shapiro, Your Business Growth Podcast

#podcast #SaaS #Entrepreneurship #businessexit

🔔 Subscribe today to get notified of new episodes, interviews, and shorts when they drop!

What if the person holding your company back is you?

In this episode of Your Business Growth Podcast, Jeremy Shapiro sits down with Derek Fredrickson, Founder & CEO of The COO Solution, to break down how Derek built a seven-figure business in its first full year—while discovering that his own strengths were creating a new growth ceiling.

Derek spent years as an operator, including a Wall Street career and helping grow his wife’s business beyond seven figures. He knew how to build systems, manage teams, create accountability, and turn ideas into execution.

Then he launched his own company and fell into the same trap he warns clients about.

Derek was getting pulled into operations and delivery while resisting founder-led sales. He even considered hiring a salesperson early—until his mentors told him he hadn’t earned the right to delegate it yet.

He needed more conversations. More knowledge of his ideal client. More firsthand experience hearing objections and understanding what buyers actually wanted.

That realization changed how he approached growth.

In this episode, we discuss:
✔️ Derek’s transition from Wall Street to entrepreneurship
✔️ Building a seven-figure business in its first full year
✔️ Why being great at operations became a founder bottleneck
✔️ Moving from operator to CEO
✔️ Building a bench of 15 fractional executives
✔️ Why Derek initially hated selling
✔️ Reframing sales from persuasion to problem-solving
✔️ Why founders may delegate sales too soon
✔️ Simplifying marketing to one offer and one primary funnel
✔️ Why 3–4 qualified leads can beat 30–40 weak leads
✔️ Showing pricing before the sales conversation
✔️ Improving an existing funnel instead of chasing new tactics
✔️ Why “you can scale simplicity—you can’t scale complexity”
✔️ Using systems, automation, and AI to reduce founder dependency
✔️ Building a business around the life you actually want

Derek also explains “your Paris”—his way of defining the freedom your business is supposed to create. For Derek and his family, that meant moving from Connecticut to Paris for what was supposed to be one year. A decade later, they’re still there.

👉 Connect with Derek Fredrickson:
• The COO Solution: https://thecoosolution.com/
• Derek on LinkedIn: https://www.linkedin.com/in/derekfredrickson/

📘 Hosted by Jeremy B. Shapiro, Author, Your Business Growth Playbook ( https://yourbusinessgrowthplaybook.com/ )

Chapters:
00:00 Simplify to Scale
00:30 Meet Derek Fredrickson
01:31 Wall Street to Operator Mindset
03:12 Joining the Wife’s Business
05:54 Finding the COO Zone
10:12 Entrepreneurial Freedom Paris Move
15:26 Building a Fractional COO Firm
19:21 Early Growth Delivery Evolution
22:56 Bottleneck and Sales Resistance
26:10 Bench Over Founder
28:06 Energetic Resistance to Sales
28:52 Warm Leads No Selling
29:16 Sales Call Anxiety
30:30 Conversation First Sales
31:46 Embrace Founder Sales
34:26 Build For Scale Systems
38:10 One Offer One Funnel
39:51 Quality Lead Filtering
41:35 PPC Hiring And Metrics
45:10 Prequalify Before Calls
47:39 No Downsell Stay Focused
49:05 Delegate Sales Later
50:55 Rapid Fire Books Mentor
54:32 Recap And Where To Find

Keywords: Derek Fredrickson, The COO Solution, Jeremy Shapiro, fractional COO, fractional executive, founder bottleneck, founder led sales, seven figure business, business growth, CEO mindset, business operations, delegation, marketing funnel, lead generation, sales strategy, business systems, entrepreneurship, operational leadership, business scaling

#podcast #BusinessGrowth #Entrepreneurship #FounderLedSales #FractionalCOO #Leadership #businessstrategy

Want to be a guest on Your Business Growth Podcast? Send Jeremy Shapiro a message on PodMatch, here: https://podmatch.com/hostdetail/your_business_growth_podcast

🔔 Subscribe for more conversations with founders and entrepreneurs sharing the decisions, systems, and lessons behind building stronger businesses.