Buying or selling a digital business is a complex, high-stakes process. We asked experienced entrepreneurs and founders to share their real stories and best advice based on personal acquisitions, exits, and growth experiences. Here’s what they said.
I'm Jayson DeMers, founder of EmailAnalytics and OutreachBloom, with over a decade of experience in B2B SaaS growth and digital marketing from building, acquiring, and advising on digital businesses.
As someone who has been through the acquisition process multiple times, here's what I look for when evaluating a digital business:
Strong, defensible niche: Is the business operating in a market segment where it can establish a clear competitive advantage? This could be through specialized knowledge, proprietary technology, or a strong brand reputation that creates barriers to entry for competitors.
Diversified traffic and revenue streams: A business heavily reliant on a single traffic source like Google Ads or dependent on one major client represents significant risk. I look for businesses with a healthy mix of organic search, social media, email marketing, and direct traffic, along with multiple revenue streams that provide stability and growth potential.
Scalable systems and processes: Can the business handle increased demand without requiring complete operational overhauls? Automated workflows, well-documented procedures, and a capable team are crucial indicators of scalability potential.
Clean financials and transparent operations: Thorough due diligence is essential. I want to see accurate financial records, clear operational procedures, and complete transparency from the seller when answering detailed questions about the business.
Success Story:
I once acquired a small SaaS business that was generating decent revenue but had plateaued in growth. After conducting a comprehensive analysis, I identified that their customer acquisition costs were unsustainably high due to a poorly optimized sales funnel and inefficient marketing spend.
By implementing targeted content marketing strategies and completely streamlining their customer onboarding process, we were able to reduce customer acquisition costs by 40% and increase monthly recurring revenue by 60% within six months of the acquisition.
This experience reinforced the importance of not just looking at topline revenue numbers, but thoroughly understanding the underlying metrics and operational efficiency that actually drive sustainable growth. Sometimes the best acquisition opportunities are businesses with solid fundamentals but execution gaps that can be systematically addressed.
Best,
Jayson DeMers
Founder
EmailAnalytics & OutreachBloom
When buying a digital business, I look at two things first: customer retention and acquisition costs. For SaaS in particular, drop-offs hurt the most. If people aren’t sticking around, growth numbers don’t matter.
With PaystubHero, we tested this ourselves.
Early on, we saw users generating stubs but not coming back. Instead of chasing new sign-ups, we rebuilt the flow to make repeat use effortless. That cut churn by 18% and doubled monthly active users in under a year. It taught me that the best acquisitions are the ones where you already see a solid product, but can spot where retention can be improved.
My advice to first-time buyers: don’t just chase revenue multiples. Ask yourself, if I owned this tomorrow, what exact levers can I pull to grow it?
If you can’t answer that in detail, you’ll struggle post-acquisition.
Kevin Wasonga
User Retention & Growth Strategy, PaystubHero
https://www.linkedin.com/in/kevin-wasonga/
I appreciate the opportunity to share insights from my experience in the digital business space. Below are my responses to your questions:
What you look for when buying/selling a digital business: When considering the acquisition of a digital business, I focus on a few key aspects. Firstly, the scalability of the business model is paramount; I look for systems in place that can handle growth without significant additional investment. Secondly, I evaluate the customer acquisition strategy. A well-defined and effective strategy can indicate a sustainable business. Lastly, I assess the team behind the business; a capable and motivated team is crucial for ongoing success.
A success (or failure) story from your experience: One notable success story involved the acquisition of a SaaS platform that specialised in project management tools. We identified that the product had a loyal user base but lacked effective marketing. By implementing a targeted digital marketing strategy and enhancing user experience, we were able to increase its user base by 150% within a year. Conversely, I once invested in a content site that seemed promising but had unclear monetisation strategies. Despite initial optimism, the lack of revenue streams led to a quick exit after just six months.
Any advice for first-time buyers or sellers: For first-time buyers, I recommend conducting thorough due diligence. Understanding the financial health of the business and its market position is critical. Additionally, consider the potential for growth; a business with room to expand can offer better long-term returns. For sellers, transparency is key. Presenting accurate financials and operational metrics can build trust with potential buyers and lead to a smoother transaction process.
I hope these insights are helpful for your article. Please feel free to reach out if you need any further information or clarification.
Best regards,
Balázs Keszthelyi
Founder & CEO | TechnoLynx
www.technolynx.com
A few years back, I sold my first content marketing agency. The entire process was fast—the due diligence, contracts, and negotiations were wrapped up in under 25 days, and we closed at a mid-six-figure price, with the agency achieving mid-five-figure MRR. What took longer was my waiting for the right buyer. I didn’t want to sell to just anyone, so I ignored most inquiries and only paid attention to serious acquisition messages that came directly to my LinkedIn or email. In business, you have roller-coaster days—somewhere between wanting to burn it all down and being more motivated than ever. On one of those dark days, I decided to sell, and months later, the right deal came along.
LinkedIn: https://www.linkedin.com/in/ugljesadj/
My name is Mircea Dima, I am the CEO, CTO, Founder, and Software Engineer of AlgoCademy, an AI-powered coding education platform. I have developed and sold digital platforms in the past, so I know how the process of acquisition and sale of online platforms works.
When purchasing, I consider two key things, user retention and scalability. High repeat revenue and low attrition are often more important than the top line growth. I have also analyzed a SaaS product that had a churn of 40 percent and although the revenue seemed good, customers were not sticky, which would have led to the failure of the product. Conversely, a very small project that I purchased with high renewal rates of 85 percent also turned into a good long term asset.
Selling is different The narrative which you give about your business is important Buyers seek clean books, systems that can be transferred and documented processes. I was able to sell a niche coding platform after making the onboarding process efficient and automating customer support. The revenue was growing consistently but what did the trick was proving that the platform could be run without me.
I would tell a first-time buyer and a first time seller not to chase vanity metrics. Put profitability, documentation and customer loyalty as a priority. A digital business can only be valuable when it does not require firefighting on a regular basis. That is what the premium on buyers is.
Mircea Dima
Founder / CEO / CTO / Software Engineer at AlgoCademy
My name is Jimmy Fuentes and I am a representative of California Hard Money Lender, an organization which assists real estate investors to obtain flexible funding enabling them to churn out projects. Although my primary area of interest is real estate, I also have the opportunity to collaborate with those who purchase and sell businesses online in the same manner as I identify what the people want, negotiate the deal and ensure the entire process goes well.
In the case of sale or purchase of digital business, what counts are the figures and the reality of the business operation. I have witnessed transactions collapse whereby the purchaser had failed to consider the ongoing expenses and had found they could not afford the business even after purchasing it. I have also helped a seller who sold the asset too cheaply because he/ she had not considered its future growth potential.
Therefore, when you are selling or purchasing a digital business, especially at first time, this is what I would recommend you to do: keep your homework and do not overlook the small print. Investors, examine the traffic figures, growth of revenue, and the scalability of the business. Vendors, put it all on the table, what is good and what is bad. The parties must also come up with clear expectations and objectives.
I hope you find this informative! If you have any additional questions, please don't hesitate to ask.
Name: Jimmy Fuentes
Position: Consultant
Website: https://californiahardmoneylender.com/
Email: j.fuentes@californiahardmoneylender.com
Linkedin:https://www.linkedin.com/in/iamjimmyfuentes
When we worked with Mississauga Foot Clinic, their website had steady visitors but underwhelming results. By tightening their SEO and local targeting, we boosted lead growth by over 290%. That’s the kind of transformation that turns a just okay site into an acquisition-worthy asset because buyers aren’t buying clicks, they’re buying predictable revenue.
My advice for first-time buyers is don’t get distracted by vanity metrics. Look at how well the business converts visitors into paying customers and whether there’s a system in place to sustain that. Even the U.S. Small Business Administration has noted that sustainable cash flow is the biggest predictor of long-term survival.
In digital acquisitions, that translates to conversion health, not just traffic charts. The shiny sites that fail are the ones nobody bothered to stress-test for monetization.
Best,
Matthew Goulart
Founder, Ignite Digital
Digital Marketing, Web Development & SEO Agency - Ignite Digital
Whether you’re preparing to sell your digital business or looking to acquire your next opportunity, these stories offer valuable lessons from those who’ve done it successfully. Have your own story to share? Reach out to us at support@acquireyet.com — we may include you in a future edition.
