Internet Security Company / Property Management App Company
Brad Miller's acquisition playbook was born from his experience as a buyer for an internet security company, which he later sold to Goldman Sachs. When his former employer declined to continue acquiring companies, Brad took the cash from his exit and began buying SaaS companies himself—specifically targeting "orphan" companies with good products but broken business models.
Brad's first major acquisition was a cloud-based internet security SaaS company doing $5-6M in annual revenue. The product was solid, but the business model was broken: it operated on a perpetual license model with no recurring revenue, despite being a hosted SaaS product that required ongoing infrastructure. Brad's first move was ruthless and simple—convert it to recurring subscription revenue. "The revenue increased 40% overnight," he explains. "Within a year, [it went] from losing a million to making a million literally overnight just by that one element."
He financed this acquisition with $5.5M in equity and $1M in debt, minimizing his personal exposure while maintaining control. By operating lean with a single CEO and CFO, and adding acquired revenue to the combined machine, he achieved significant operating leverage.
Brad's growth strategy centered on paid-per-click advertising, which he personally managed and optimized. His unit economics were simple and elegant: "If we could spend a dollar, make a dollar right away, we were even and then any renewals or upsells thereafter were just gravy." He spent $300,000-$500,000 per month on ads, but the payback was immediate, making the capital extremely efficient.
Over 10 years, Brad scaled the company to $20M in revenue and $6M in profit before selling to TZP, a New York-based private equity fund. In his best year, he took $6M in personal dividends. However, the PE buyer made critical mistakes post-acquisition. They hired professional management and consultants who deemed his operation "too fast and loose and not structured enough"—despite a decade of consistently rising revenue and profits. Most damagingly, they outsourced the PPC advertising to an agency, believing his approach wasn't scalable. Returns on advertising "went from what they were to half of what they used to be." The business subsequently crashed. Two years later, it had declined from $20M to $12M in revenue and from $6M to $2M in profit.
Undeterred, Brad has continued his acquisition strategy. In mid-2021, he acquired a bootstrap property management app from a Chicago-based founder doing $3M in annual revenue at a $6M pre-money valuation. The founder was conflicted about reinvesting profits versus taking cash out. Brad's solution was surgical: he invested $3M to buy 51% equity, but insisted the founder take $3M personally to eliminate the conflict, then reinvest 100% of business profits into expansion. "The two million ARR, four million cash. He took all four million off the table." A year later, the business had grown to $7M ARR—more than doubled—through geographic expansion beyond Chicago, where it had dominated despite well-funded competitors. This deal worked, and Brad doubled his money in year one.
Similar Companies
Active Campaign
$4.2M/moActive Campaign started in 2003 as an on-premise email marketing solution built by Jason Vanderboom to fund his fine arts degree. After 10 years and 8 employees generating a couple million in revenue, he transitioned to a SaaS model starting at $9/month. The company now has over 60,000 customers generating over $50 million annually and employs 330 people, growing primarily through organic adoption, partnerships, and focus on the SMB market despite pressure to move upmarket.
Ahrefs
$3.3M/moAhrefs is a bootstrapped SaaS company providing SEO and backlink analysis tools, currently generating over $40M ARR with 45 employees. After joining in 2015, Tim Solo transformed the blog from 15,000 to 250,000+ monthly Google visitors by shifting from publishing what they wanted to write about to targeting keywords people actually search for, creating high-quality content with direct product integration, and continuously updating articles to accumulate backlinks. The company breaks conventional marketing wisdom by not using customer personas, growth hacks, or detailed analytics—instead focusing entirely on product quality and audience education through blog content.
Calendly
$2.5M/moTope Awotona founded Calendly after three failed startups taught him the importance of solving real problems rather than chasing money. He spent six months validating the scheduling tool idea by studying competitors' products and user forums, then went all-in by emptying his bank account and hiring engineers in Ukraine. Calendly achieved product-market fit through a freemium model that optimized for invitee experience, growing to 4 million users and $30M ARR largely through organic viral growth and word-of-mouth.
LMS365
$2.5M/moLMS365 is a SaaS platform built for the Microsoft ecosystem that raised $20M in 2023 at a $100M valuation, based on $20M ARR. As of April 2024, the company has grown to $30M ARR with a 200-person team. The company is targeting $40M ARR in 2024, demonstrating strong momentum in the enterprise learning management space.
QuestionPro
$2.5M/moQuestionPro is a bootstrapped SaaS survey and feedback platform that grew to $30M ARR primarily through strategic acquisitions of smaller companies, buying them at 2x multiples. The company's growth strategy focused on consolidation within the survey/feedback tools market rather than traditional marketing channels.