Aug 16, 2022 · 26m · startup-acquisition-stories
Startup Acquisition Stories with Joe Speiser - Partner at HamptonVC
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of SaaS Acquisition Stories, host Andrew Gazdecki interviews investor Joe Speiser on his playbook for acquiring, rehabilitating, and scaling distressed micro-SaaS businesses. Speiser shares actionable strategies on deal sourcing, fast asset purchases, overcoming platform risks, and transitioning from quick software flips to long-term holding company models.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Andrew holds 24.9% of the talking time here. How this is scored →
Andrew as informed peer 5.0 Guest teaching 5.0 Guest disagreement 1.4 Andrew pushing back 1.5
speaking balance: gold is Andrew, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:55 Reframing Andrew's mentorship advice as overly reactive
Joe directly counters Andrew's suggestion that founders should wait for mentors to notice their work, arguing that waiting is too passive and one must proactively message suitable targets.
Hardest push from Andrew ▶ 11:29 Andrew's firm warning against bypassing escrowWhen Joe mentions that he often skips using an escrow service on smaller acquisitions to save time, Andrew immediately cuts in twice with concise pushback insisting he should use escrow.
Biggest teaching moment ▶ 22:47 Masterclass on distressed deal sourcing via startup credit providersJoe educates Andrew on an innovative acquisition sourcing strategy: contacting Ramp and Brex directly to buy the assets of companies struggling to service corporate debt.
Andrew holds their own ▶ 20:56 Andrew citing firsthand partnership data with restructuring firmsAndrew demonstrates industry authority by revealing partnership discussions with a major insolvency restructuring firm forecasting hundreds of distressed tech sales.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Andrew as informed peer | Guest teaching | Guest disagreement | Andrew pushing back | Why |
|---|---|---|---|---|---|---|
| Joe Speiser on Flipping Brax for a 10x Return | 4 | 5 | 1 | 1 | Andrew kicks off by prompting Joe to share his deal history on MicroAcquire. Joe explains his strategy of buying distressed assets like Brax and a Shopify app to fix technical debt and flip quickly. The tone is casual and highly collaborative. | |
| The Thrill of Sourcing and Managing Sub-30 Person Teams | 5 | 4 | 1 | 1 | Joe details why he prefers sub-30 person teams to avoid middle management and recalls how Facebook algorithm changes crippled his previous 120-person business. Andrew agrees enthusiastically with the lesson of owning rather than renting an audience. | |
| Targeting Old Listings and Low-Rated Software Products | 4 | 6 | 1 | 1 | Joe explains his counterintuitive strategy of sorting deal listings by the oldest and targeting software products with 1-star reviews caused by neglected customer support. Andrew listens attentively and prompts him for further deal specifics. | |
| Fast All-Cash Asset Purchases and Due Diligence Practices | 6 | 4 | 1 | 3 | Joe outlines his fast, all-cash asset acquisition process using standardized contracts without attorneys. When Joe admits he skipped escrow on a deal and sweated when the seller went silent, Andrew interjects with pushback that he definitely should use escrow. | |
| Merging Acquisitions and Long-Term SaaS Growth Goals | 5 | 5 | 1 | 1 | Joe discusses merging two recently acquired SaaS products and shares red flags he spots in seller listings, such as mismatched metrics and disingenuous reasons for selling. Andrew validates these insights as practical advice for prospective sellers. | |
| Leveraging Twitter Resources and Securing Industry Mentors | 5 | 6 | 3 | 2 | Andrew suggests that the best way to get a mentor is to build in public and let mentors reach out reactively. Joe politely rejects this framing, asserting that founders must proactively message specific, reachable operators on Twitter. | |
| Macroeconomic Trends and Opportunities in Distressed Startups | 6 | 6 | 2 | 2 | Andrew shares market intelligence regarding bankruptcy restructuring partnerships, while Joe analyzes the macro labor market and outlines a clever lead-generation tactic of partnering with corporate credit card providers like Ramp and Brex to buy distressed venture-backed assets. | |
| Holding Company Models and Inspiration from Industry Operators | 5 | 4 | 1 | 1 | The conversation concludes with Joe and Andrew discussing long-term holding company operators like Tiny and Enduring Ventures, drawing comparisons to the Berkshire Hathaway permanent capital model before wrapping up. |
Statements from this episode (14)
Speiser sold Brax for over a 10x return in 18 months
“We ended up selling it for over 10 times what we paid.”
Speiser doubled his investment flipping a Shopify app in six months
“We ended up holding that one for six months and doubling our money, which I didn't like the space. I don't like being reliant on one platform.”
LittleThings generated $70M revenue before Facebook algorithm changes destroyed it
“We were doing, you know, 60, seventy million a year in revenue. And then Facebook just dropped the hammer on us one day and kind of destroyed our business, which was my point with like Shopify.”
LittleThings built 50 million Facebook followers before the platform revoked distribution
“I had like, fifty million followers on Facebook at one point, right? But they were rented, and Facebook decided to take them back, right?”
Speiser bought his first software business for six figures, exiting for seven
“The first business we bought for low six figures and sold for seven figures.”
One-star software reviews signal distressed opportunities with easy operational fixes
“I also tend to look at the overall reviews for each company and the more negative the reviews are from customers, the more likely I'm going to be interested. I know that sounds really perverse. It doesn't make a lot of sense to a lot of people, but it has to b…”
Speiser handles his own acquisition legal work without using lawyers
“I don't have a lawyer that does any of this. I do all the legal myself. It's not terribly complicated when I could use your forms off your site, and we all agreed to not touch them and mark them up.”
Fast all-cash offers can win micro-SaaS acquisitions at lower purchase prices
“I don't need an SBA loan, which slows things down pretty dramatically. So I can offer them a low ball offer, but all cash all up front within like 48 hours. Right? So for people who've been sitting there for a while trying to sell their SAS, that's really attr…”
Founders usually sell because their skills can no longer grow the company
“Everyone always says the same thing about why they're selling. Which is kind of like, you can see through it, like, oh, you know, I want to do something else. I'm bored of this, which I get, and it could be honest, but more times than not, it's for a specific …”
The Hustle founder Sam Parr receives 500 Twitter direct messages per day
“You need someone who's, you know, successful, but not, like, celebrity successful. Otherwise, their DMs are probably flooded. Like, Sam, Sam Parr, who I was just talking to a couple minutes ago before we got on this, he said he gets 500 DMs a day.”
Almost every startup pitching Speiser is seeking emergency bridge funding
“I do a bunch of angel investing and every, almost every single contact that has reached out has asked for like a bridge round or some sort of emergency, you know, cash infusion. They're all looking at somewhere between six and eight months of runway before the…”
Startups that raised $40M will sell for $1M-$2M within 12 months
“And then the other thing I'm looking for is I'm waiting for that like company that raised 30, forty million dollars and now burned through it all, but built an amazing piece of tech to go and micro acquire and sell for a million or two. Like, It's inevitable. …”
Speiser: Partner with Ramp and Brex to source distressed startup acquisitions
“No, what I would do is like to elephant hunt again, I would contact like ramp and Brex, Because they see everyone's bank account, they see the debt, right? They know who's about to go under and who's not, and it's in their best interest to not lose money. I do…”
Enduring Ventures acquired Hawaii's only motorcycle rental business
“He bought like a Harley Davidson rental company in Hawaii, like the only motorcycle rental company in Hawaii, right? So he has monopoly on all motorcycles, if you want to rent one in the entire, on the entire island, and it just prints money.”