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.
- •Brad identified that converting a SaaS product from perpetual licensing to subscription revenue created immediate 40% revenue growth, demonstrating that business model changes can unlock hidden value in otherwise solid products.
- •His paid advertising strategy worked because he maintained direct control and obsessive focus on unit economics (spend $1, make $1 immediately), which created capital efficiency and measurable ROI that justified scaling ad spend to $300-500K monthly.
- •Acquiring orphaned companies with good products but broken fundamentals allowed him to apply a repeatable playbook (subscription conversion, lean operations, paid acquisition) across multiple assets and compound returns through a roll-up strategy.
- •His decade of consistent revenue and profit growth proved that a lean, founder-led operation with simple unit economics could outperform professional management—a principle validated when PE buyer's structural changes cut advertising returns in half.
- 1.Audit any SaaS product you acquire for monetization misalignment: if it's hosted software operating on perpetual licenses, immediately convert to subscription billing and measure the revenue lift.
- 2.Build your paid advertising strategy around a single, trackable unit economic metric (cost-per-acquisition vs. immediate payback period) and personally optimize campaigns until you achieve consistent positive unit economics before scaling spend.
- 3.When acquiring companies, minimize your personal capital exposure by using equity/debt structures that let you maintain operational control while the acquired asset's revenue contributes to your combined entity's profitability and reinvestment capacity.
- 4.Resist organizational bloat during scaling: operate with a skeleton crew (single CEO, CFO, core team) and rely on process discipline and founder involvement rather than hiring professional management until unit economics are proven at scale.
Similar Companies
247.ai
$25.0M/mo247.ai, founded by PV Cannon in 2000, is an AI-powered customer service automation platform serving over 150 enterprise customers with $300M+ in ARR. The company raised only $20M from Sequoia (2003) and bootstrap, achieving 10% net profit margins while maintaining a 12-month CAC payback period and 100% net revenue retention. Despite a security breach setback around 2018, 247.ai has recovered and recently achieved 20% new revenue booking growth in their best quarter.
iCIMS
$13.3M/moiCIMS is a bootstrapped SaaS provider founded in 1999 that dominates the talent acquisition software market as the #2 player, serving 3,500 enterprise customers with an average monthly spend of $4,000. The company exited 2017 with $160M ARR and is targeting 25%+ annual growth while maintaining profitability, recently acquiring Text Recruit to expand into candidate messaging and recruitment advertising.
Zoom
$12.0M/moZoom is a freemium SaaS video conferencing platform founded by Eric Yuan in July 2011 after he left Cisco to build a next-generation collaboration solution. The company has grown to 850,000+ paying customers across individual, SMB, and enterprise segments, generating over $12M in monthly recurring revenue with approximately 100% year-over-year growth. Rather than focusing on customer stickiness or aggressive growth targets, Zoom emphasizes customer happiness and organic word-of-mouth acquisition, which has proven highly effective in driving viral adoption.
Madwire
$10.0M/moMadwire is a comprehensive SaaS platform for small businesses (1-100 employees) that combines CRM, payments, invoicing, billing, e-commerce, and multi-channel marketing tools in a single platform. Founded in 2009, the company has grown to $120M ARR serving 20,000 customers with an average revenue per user of $500/month, while maintaining strong unit economics ($3,000-$4,000 CAC with 3-month payback) and recently turning profitable with a focus on reaching 15-20% EBITDA margins. The company is exploring an IPO within 12-18 months without having raised substantial capital beyond an initial $7.5M.
SwiftPage
$7.0M/moSwiftPage is a CRM and marketing automation platform founded in 2001 that targets small businesses. Under CEO John Oshel's leadership since 2012, the company scaled from 60,000 customers with $26.2M revenue in 2015 to 84,000 customers today with an estimated ARR of $36M+, maintaining 1.5% monthly logo churn and a 6-7 month payback period with a sub-$500 CAC.