13 Oct 2026
The Deal That Froze Our Payments with Dmitry Dragilev
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
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