Andrew Pierno

Founder of XOXO Capital

AI Generated Content

Spotify Amazon Apple Listen: Watch: https://youtu.be/JbIkoGGhoak Like much of the rest of the world, we're experimenting with AI generated content. Last week, we bought Supportguy.co and needed some blog posts. We used this process to create the first 5 blog posts to seed our blog. The

Acquisition #8 - Supportguy.co

We delve into acquisition #8 - SupportGuy.co, a micro SaaS that is set to revolutionize customer support with its AI-powered chatbot. This acquisition aligns with our vertical integration strategy, to own and optimize all tools we use to manage our portfolio.

Maybe Thesis - v3

Spotify Amazon Apple Listen: Watch: We're supposed to be buying boring SaaS businesses that cash flow slowly and consistently. On the small end of the market, that's a little challenging to do. Often, the way that plays out is buying a small B2B enterprise SaaS company that does something pretty

Mastering The Art Of Giveaways

Audio Spotify Amazon Apple Video 💡Fun update. Got a cease and desist order from linkedin over one of these giveaways. Looks like they were working too well! I of course complied and am also of course very very sorry. Over the past 4-5 months we began experimenting with giveaways. We've

Sale #3

We sold Workclout. It was the one company in the portfolio that no longer fit with our relatively new focus on PLG companies. That's not to say we wouldn't acquire a non-plg type company in the future but it would either have to be: 1. Bigger 2. After we reach

Anatomy Of A Turnaround

We accidentally bought a turnaround. Now, to be clear most of the products we've purchased would fall into the distressed category. 2 have been proper distressed venture deals (former YC companies). But even the tiny ones that are half baked, I'd still consider those distressed. They are! You take them

March 2023 Round Up

If you've been missing my dulcet tones check out my most recent interview with Jaryd Krause from Buying Online Businesses Audio Version ‎Buying Online Businesses Podcast: How To Start Buying & Flipping Small Saas Businesses with Andrew Pierno on Apple Podcasts‎Show Buying Online Businesses Podcast, Ep How To Start Buying

Feb 2023

What up XO fam. I've had plenty of caffeine this morning so I'm going to be firing from the hip on this one. Example: Guys (and gals). Listen. buying MRR is lovely. Here's proof (and 13 people agreed). If you haven't tried it. You should. Hey just FYI buying MRR

Hype

Staying disciplined is hard. With all the hype around "AI" or more specifically all the hype around gpt-3 enabled products, it's never been more important to stay disciplined with your investing thesis. Moments like these create fortunes. A few of the 2,000 AI writers are amazing business. Most will

Platform Risk

Platform risk is when another company controls your destiny. This week there was a big scare with Twitter's enforcement of a policy they claim had been around for a while. Twitter’s new developer terms ban third-party clients | EngadgetTwitter has quietly updated its developer agreement to make clear that app

Long live the minnows!

XO is 2.5 years old. We're starting to have some history. Recent milestones include the first ever product we have grown 10x since acquiring it. We bought Screenshot API, our very first acquisition, when it was making $500 MRR. It's now over $5k MRR. $500 MRR is obviously peanuts

Cash Accumulation

When we started two years ago I naively thought I'd read enough Twitter threads to understand that basically all we needed to do to win was: 1. buy good businesses (hard) 2. accumulate excess cash (hardest) 3. redeploy that cash (harder) However, we now have two years of operating history

Turning $300k into $1.3M (2022 Annual Review)

2022 proved XO's business model. We were able to source deals, close them, grow them, and in some cases sell them. We grew to 6 full time people (not including myself and Henry). We joined the 6 figure club and proudly bootstrapped our way to low six figures in revenue

Acquisition #7 - Cold DM

This week we closed on a Twitter DM tool. Check It Out It's the smallest deal we've ever done. Are we going backwards? What's up? We're working on our largest deal ever. Hopefully it will close early next year, we're on a path for that one and it's looking great,

Oct 2022 Portfolio Updates

The three co-founders of XO got together last weekend in South Carolina for a weekend of golf and just hanging out. I am by far the crappiest golfer on the team... it's truly an evil sport. I think I'm also the shortest. Anyways ... We get together at least once a

Some Podcasts + 1 Growth Tactic To Steal

Your boy was on two pods the past few weeks.  Can I still talk like this at 33? The Startup Blueprint Episode 9 - Don't Build It.... Buy It? Acquiring a $1M ARR Portfolio This is a great intro from the perspective of Indie Hackers looking to buy their first

September 2022 Updates

I don't know about you guys but September felt weird. Between all the rate hikes, inflation data, stock market drops, and crypto chills it was a tough month for sales. Also feels like nobody in tech is around August and September (myself included this year!). TLDR; September sucked. SaaS is

How To Buy A SaaS Business Via The SBA - Part 1

We have a deal under LOI right now that we plan on financing via the SBA. I'd like to document that process step-by-step since as far as I can tell, most of the Twitter advice on this is being shilled by charlatans who don't know jack about the process. This

Buying Vs Building

Apple Podcast Spotify Amazon Let's take a look at why you might want to buy a business vs build one. I've done both. I've exited a company I built from scratch. I lost a lot of hair, but ultimately did get a decent pay day. I am now personally funneling

Enterprise (Sales Driven) vs Product Led Growth Companies

💡Thanks to the 450 new followers and 50 new subscribers. If you're new here, these are XO's notes on buying SaaS companies. Each week I try to break some part of the process down to help others acquire businesses. It is not strictly true to say that there are only

Your First Acquisition

I've been having 3 ish conversations a week about people wanting to buy their first business so I thought I'd put everything I know into one post. This isn't that post (sorry ... time) but it's the closest thing to it at the moment :) This one is going to be a

August 2022

Highlights: * 💰 Total MRR: ~$26,737 (+/- a few hundred) * 👏 Sold Sentiment Investor! * 🚣 Now at 5 FT employees. Biggest Win: * Sold sentimentinvestor.com - it went to a much better forever home :) Biggest Fail: * churn on inlytics. Inlytics uses a chrome extension to check linkedin for post performance. When anything in

Flywheel

This month I'm working from Santa Teresa, Costa Rica. It's a beautiful one-street town in the middle of the jungle with excellent surf. I feel like I'm about 2 years late to getting on the digital nomad bus. I've always been a late bloomer... Of course last week I posted

The Uncanny Valley Of Micro PE 🐌

In aesthetics, the uncanny valley (Japanese: 不気味の谷bukimi no tani) is a hypothesized relation between an object's degree of resemblance to a human being and the emotional response to the object. The concept suggests that humanoid objects that imperfectly resemble actual human beings provoke uncanny or strangely familiar feelings of uneasiness

How Not To Buy A Bad Deal & Our 2nd Sale!

At the tail end of last week, we finalized our sale of Sentiment Investor (SI). It's in much better hands now with a team that can execute on the vision. SI was a tough one for us. We had a bad transition when we bought it, lost 100% of the