👋What’s New
Hey everyone!
Started this week with an intro call for a 20 year old online tutoring business with insane margins. Asked the seller how she sources customers and she said a "secret social media algorithm" thing and I pretty much zoned out from there. You just know when someone says something like that this will be a waste of time or a scam.
On the RaffleLink front though, we're making solid progress on 2.0! The team's been grinding through design reviews and I've been deep in the technical weeds fixing database connection timeout issues and setting up Web Application Firewall configs. Nothing glamorous, but we're tightening the ship. Launch keeps getting pushed back a week here and there, but that's the reality of building something properly.
Alright, let's dive into some deals and lessons this week.
— Eddie
💼 3 Businesses For Sale
1. AI Headshot Generator SaaS — Fully Automated
Revenue: $300K+ | Asking: $350,000 | Multiple: 2.2x | Margins: 60%+
This is an automated AI headshot platform that generates professional headshots from selfies. It's been running on autopilot with minimal owner involvement.
Why it's interesting:
Low multiple — 2.2x for a profitable SaaS with 60%+ margins is rare
Automation-first — business runs itself, owner barely touches it
Evergreen demand — professional headshots aren't going away (LinkedIn, corporate, job seekers)
B2B upside — current focus is consumer, but enterprise/team plans are untapped
Concerns:
AI commoditization risk — headshot generators are multiplying; defensibility unclear but you already have customer base and brand with this business
Single product — no diversification but risk is partially accounted for in low purchase price
Quality differentiation — hard to build moat when underlying models (DALL-E, Midjourney, etc.) are available to everyone. More research needed on how this is built.
Best for: Someone who can add distribution/marketing muscle or bundle into existing B2B SaaS portfolio.
2. Bariatric Supplement Business — 94% Recurring Revenue
Revenue: ~$200K | Asking: $965,000 | Cash Flow: $194K | Multiple: 5.0x
A 6-year-old supplement company targeting people who've had bariatric (weight loss) surgery. Single SKU with extremely high repeat purchase rate.
Why it's interesting:
94% recurring revenue — once someone starts, they keep buying (medical necessity)
Underserved niche — bariatric patients have specific nutritional needs that mainstream brands don't address
Single SKU simplicity — no complex inventory, no product line confusion
Remote operation — run from anywhere, no physical presence required
Built-in moat — brand recognition in a specialized medical community is hard to replicate
Concerns:
5x multiple is fair but not cheap — you're paying for the recurring revenue profile
Regulatory risk — supplements face evolving FDA scrutiny
Key person risk — relationships with bariatric surgeons/clinics for referrals?
Growth ceiling — niche market has natural limits
Best for: Someone with health/wellness background or existing supplement operations who can add SKUs while preserving the core recurring base.
3. Plant-Based Recipe Blog — 13 Years, 1,100+ Posts
Revenue: ~$131K | Asking: $327,515 | Cash Flow: $131K | Multiple: 2.5x
A 13-year-old WordPress food blog focused on plant-based smoothie recipes. Over 1,100 pieces of content with an SEO team actively updating old and new posts.
Why it's interesting:
2.5x multiple on cash flow — very reasonable for a content asset with this history
13 years of domain authority — you can't fake this; Google trusts old sites
Multiple revenue streams — ads, affiliate, premium content
AI-leverage opportunity — can use AI to systematize content updates, expand into video, create recipes at scale
Concerns:
AI disruption risk — Google's AI overviews and ChatGPT are eating into recipe search traffic
Algorithm dependency — one Google update can tank traffic overnight
Niche saturation — plant-based/smoothie space is crowded
Best for: Someone who’s resourceful and into food and health. You can do a lot with just the subscriber base and email list — if those exist, the business has optionality beyond Google.
💡 2 Insights This Week
The SBA Repeating Acquisition Strategy
Most people think SBA 7(a) loans are one-and-done. Wrong.
Here's the play: You can have up to $5M in outstanding SBA guaranteed loans per business. But here's where it gets interesting — once you pay off an SBA loan, that capacity is fully restored. Even better: if you refinance an SBA acquisition loan into conventional financing (after building a track record), you unlock your full $5M capacity again for the next deal.
This creates a compounding acquisition machine:
Use SBA 7(a) to buy business #1 (up to 90% financing)
Operate for 18-24 months, build track record
Refinance into conventional debt (better rates, no prepayment penalty)
Full SBA capacity restored — ready for acquisition #2
Repeat
The kicker? If you own businesses in different industries (different first 3 NAICS code digits), you get a separate $5M cap for each. That's $10M in simultaneous SBA capacity.
And for second locations or expansions of an existing business? Zero down payment under SBA expansion rules if you're a proven operator.
The Silver Tsunami Is Real (And It's a Buyer's Market)
Here's a stat that should change how you think about deal flow:
Over half of all privately-held businesses with employees have owners over age 55. Baby Boomers own roughly 40% of small businesses in the US, and an estimated $10 trillion in private business assets is coming to market as they retire.
10,000 Boomers turn 65 every single day. Most don't have succession plans.
Meanwhile, on the buyer side: 44% of business buyers now identify as "corporate refugees" — mid-career professionals leaving traditional jobs to buy small businesses. Another 15% report being recently unemployed.
What this means:
Supply is exploding — motivated sellers with no succession plan
Demand is sophisticated — buyers are experienced operators, not naive first-timers
Quality matters more — "well-run, profitable businesses are going under contract 2-3x faster than normal" (BizBuySell)
The implication? If you're looking to buy, there's unprecedented deal flow. But the good ones move fast.
And if you're thinking "maybe someday" — the window where supply outpaces demand won't last forever. As more corporate refugees enter the market and Boomers finish exiting, the dynamics will shift.
📖 1 Story
The PhD Who Can't Find a Job (And Why Buying a Business Might Be the Answer)
A close friend just finished his PhD in biomedical engineering. Niche field, years of rigorous research, genuine expertise.
Now he's job hunting. It's brutal.
He doesn't want academia. Industry jobs in his field are scarce. And he's not qualified for the pivot roles — startups want operators, SWE roles want coding experience he doesn't have.
Months of applications. Rejections. Ghosting.
Last week I pitched him something unconventional: buy a small business instead.
His reaction: "I don't know how to run a business."
Mine: "Neither did the person selling it when they started."
Here's what most people don't realize about acquiring a small business:
You're not just buying a business. You're buying:
A job (that you control)
Equity (that grows with your effort)
Experience (that compounds daily)
Optionality (sell it, grow it, or use it as a launchpad)
He has family financial backing that could cover a down payment. He's analytically rigorous. He can learn.
Is it scary? Absolutely. But so is sending your 200th application into the void.
The job market in 2026 is telling a lot of talented people: "We don't have a seat for you."
Maybe the answer isn't finding a seat. Maybe it's building your own table.
See y’all next week,
@eddieacquires