Adam Robinson

$10M ARR is the FU MONEY of SaaS. At $10M ARR bootstrapped, you and your co-founder clear $1M+/year in salary and dividends easily. You can sell instantly for $30-40M. There are hundreds of EBITDA buyers at this level vs. a handful at $1B valuations. From here, you can do whatever you want. Hire a CEO and work 1 hour/week. Grind 100 hours if that's your thing. Raise $50M from a position of strength. Scale to $25M ARR with 25 people and pay yourself $10-15M/year. Most companies never get here because VCs show up early with decacorn dreams and money you don't need. That capital interferes with the one thing that makes you great: product-market fit. Bootstrapping to $10M ARR is easier and less risky than creating a VC-backed unicorn, with a far higher probability-weighted outcome. If you can find PMF and use customer money to get to $10M, you can do anything you want with your life.

I have done 0 to $1M ARR 3 times… …If I lost everything (again) and had to get back up (again), this is exactly what I would do: 1. Start posting organic social content about what I'm an expert in, which is B2B SaaS. 2. Hone the craft and build an audience. 3. In doing so, identify gaps in the market I could fill with a product or a service. 4. Start with the service. Do things for people. 5. Automate the service. That's the way I've done it 3 times, and that’s the way I would do it again (if needed).

> that's cringe > you're not ambitious enough > if that's real, you should sell your company pov: you build in public, and this is what you will hear… until what you’re building works. Then they double down. But at least you’re scaling. I STILL get comments like this on my content, but you have to do what you believe in even if others might not agree. Build in Public, thank me later.

“Should we be investing in SEO for our 2 year old SaaS?” Me: “Well, our organic traffic is up 201% and 27-35% of those visitors are signing up for RB2B. These are a few other BANANAS results from the last 6 months working with ”: > Non-branded clicks: up 43% (4,270 vs 2,980 on 1.36M impressions) So, SEO is driving LOTS of clicks > Engaged sessions: up 90% (33K to 62K on total sessions only rising 11%) So, SEO is driving LOTS of engagement. > High-value keywords: 164 vs 44 when we started (+270%) So, SEO is driving LOTS of targeted pageviews. …Should you be doing SEO?... …you tell me.

@amandabradford @dailycopywriter @theleague THANK YOU FOR THIS GREAT COMMENT. And thank you for telling founders never to sell hahaha

Same story with my company @theleague growing profitable but not venture scale $40M exit on $2.3M seed raised $15M arr top line thank god I charged my customers early and realized self funding was better than a super diluted series A that would have easily put me in zombie mode and lost majority. I owned 55% at exit and didn’t need to sell but wanted to take money off table and also put my baby in the best possible home that would grow it into its potential. now though I wish I had done what he did and just hired an operator / replaced myself as ceo, kept the equity and just distributed profits as it was an amazing cash machine $6M ebitda on $15m and I was running it with 12 people and 20 hrs/week and the acquiror still hasn’t hockeysticked it after 4 years despite me handing over all my growth ideas on a silver platter, not implementing any of them or giving us any resources, increasing the marketing budget 5x but not letting me control it/central marketing putting it only in FB ads pushing me out as soon as they legally could and firing most of my AllStar team team so i would actually tell founders DO NOT SELL A PROFITABLE business EVER even if the acquiror charms you I would buy it back if I could but I guess it’s the only one growing in the entire portfolio (besides the golden child) which isn’t saying much considering ☠️🫠😢 I guess good to know for next one, build back better and don’t sell out? Also solo founders for the win!

THIS IS AN INCREDIBLY IMPORTANT ACQUISITION FOR FOUNDERS: What's not said in this "we only raised $8M and sold for $105M" is the little-known fact that the reason they only raised $8M was that several years ago, nobody would do a Series A for that biz. Which is why Kennan replaced himself as CEO and moved on to ICON. He was upset about it at the time. That moment he couldn't raise was the single best thing that ever happened to him. Here's why this matters for founders: > Selling a business for $105M when you only raised $8M is LIFE CHANGING. > For the same reason he couldn't get the Series A done, I'm not sure a business like that (sticky but sells to a small TAM of elite Shopify brands at $500/mo) is saleable at $500M+. > Had he been "lucky enough" to get the A done and raised at a $200-250M valuation, the exit hurdle would've been $600-750M. > Recharge likely wouldn't be a buyer there ($2.1B val at absolute peak valuations). Not sure anyone would be because if you're buying Skio at $600-750M, you think it's going to $2B. > Skio (which would be the same, GREAT business) would very likely be stuck in a zombie state, pushing for a valuation it was never meant to reach. Like so many others. Ryan Allis said something on my show that's stuck with me: "If you have to raise money, keep it at 1x your ARR at the time." All because it maximizes your optionality. You can sell a great biz for $100-150M and go do whatever you want. You can keep running it. Or you can keep the equity, hire someone else to run it, and go bigger (like Kennan). If you're a founder, keeping a low 9-fig exit on the table is an incredibly smart move. Kennan did it by accident. You should do it on purpose. You only need to get rich once. Have as many paths to that place as possible. (Oh, and PS: the other reason he was able to sell? They were a growing, profitable business. Why do more people not live life this way?!?!)

If you don't know who's visiting your website, you're leaving deals on the table every single day. RB2B shows you exactly who's checking you out for free. No demo required. Just plug it in: rb2b.com/?utm_source=X&…

Everything I'm learning from scaling to $30M ARR bootstrapped straight into your inbox. Tactical breakdowns, workshop invites, and the stuff I don't post on social. Subscribe here → newsletter.rb2b.com

If you're stuck at $500K ARR, you probably never had product-market fit… (If you had it, you would have blown past $500k ARR and you would not be reading this tweet) This is what will always be present when PMF is real: 1/ you say one sentence, and people stop what they're doing (visible, enthusiastic surprise) 2/ people ask how to buy before you've built it 3/ word of mouth starts without you doing anything 4/ you ship a shitty MVP, and people still love it If none of these happened…you probably never had PMF Take this as a sign to run the check! BTW there are a few different schools of thought on how to find it. Gail Goodman from Constant Contact calls it the “Slow SaaS Ramp of Death” - PMF is just the sum of a million things done right over a long time. Parker Conrad's version is the compound startup - build everything, undercut on price, and PMF emerges from the integration. Requires an unbelievable amount of founder skill. Both worth your time - links in the comments.

For further reading: Gail Goodman - The Slow SaaS Ramp of Death: businessofsoftware.org/talks/gail-goo… Parker Conrad - The Compound Startup: saastr.com/rippling-ceo-p…

The markets that made me the most money looked terrible on paper. They were underserved. Relatively unattractive. The kind VCs pass on because the TAM looks too small. That's the point. Boring means: • Customers who actually need it • Real money hitting your bank account every month • Nobody else is trying to build the same thing $10M ARR in a boring market is the FU money of SaaS. The TAM being small is a feature, not a bug.

Bootstrapping at scale = your team living however they want. My COO reminded me of that. We hired her for $10 an hour to fix a billing issue. 1. She'd been out of the labor force for 8 years. 2. She has 5 kids and was an investment banker before stepping away. 3. Within 6 months, she was on our executive team. She told me, "I had planned to get to where I am now in 5 years, but you gave me that chance in 6 months." This is what building a company on your own terms actually looks like.

If you don't know who's visiting your website, you're leaving deals on the table every single day. RB2B shows you exactly who's checking you out for free. No demo required. Just plug it in: rb2b.com/?utm_source=X&…

3 changes to our cold email copy 5x'd demos booked at Retention(.)com. The old version led with price. Subject line: "$18 per lead is a lot." Body explained: > What we do > Mentioned our free trial > Asked if they had thoughts Reasonable email that got us 3 demos a week. The new version leads with the offer. Subject line: "10k leads on us." Subhead: (not kidding). Body is two sentences: > What we do > What you get free No contract, cancel anytime. One question at the end. This got us 15 demos a week. And this is what actually changed: 1. One idea per email. The old version talked about price per lead, ESP resolution rates, and what we do. 3 different things. The new version talks about one thing: a crazy free offer. 2. A subject line that stops the scroll. "$18 per lead is a lot" is not the punchiest way to describe ourselves. "10k leads on us" followed by "(not kidding)" is a $100M offer framing - so good it feels stupid to say no. 3. Clear and concise. The old version didn't express the clearest essence of our pitch in as few words as possible. The new version punches you in the face with the "so what", and then proves it. Cold email is hard. Writing great copy for cold email is even harder. So when you sit down to write your next outbound email: one idea, a killer subject line, and seek out the $100M offer framing.

This is what bootstrapped ownership actually pays: At $5M ARR: hundreds of thousands. At $10M ARR: a million. At $15M ARR: more millions. At $25M ARR: more and more millions. No investors or dilution. Every dollar yours.

Someone gave Claude Code a domain name, and 4 hours later had Typeform. When someone can reproduce a year-old SaaS product in an afternoon, the product itself is not the moat anymore. Many people in SaaS heard that story and either panicked or dismissed it… ..But both reactions are wrong. Nobody's going to vibe code HubSpot. The enterprise will keep buying enterprise software. But the actual shift is that it used to be hard to get software built. You NEEDED engineering talent. That was a massive filter, and it's basically gone. That's why SaaS stocks are getting hurt, because the pool of potential competitors just got massively larger overnight. It takes a one-in-a-million founder to take down a publicly traded SaaS. That person has always existed. The question is how many more of them can get started now that the engineering barrier is gone. My answer: at least 10,000 times more will try. A few will be Elon Musk-type guys. The companies that come out of this in good shape are the ones that built something genuinely hard to replicate. A unique data asset A network effect That's exactly what I'm trying to build for my next act - a dataset built entirely for AI agents.

$30M ARR Owned all of it Dropping $20M to the bottom line every year That was @RossAndrew. The most influential person on what I wanted to build when I started GetEmails (now Retention(.)com). My co-founder Diana worked for him. I looked at that and thought, why are there not more people doing it that way? Surely $30M ARR is easier than 100s of millions…yet so many people are pursuing 100s of millions of ARR with venture funding. I've literally never heard of anyone else who's done it the way this guy's doing it. That was the first time I was just like, yeah, that's what I'm gonna try to do. Part of the reason I'm so loud about what I'm doing is that I want people to hear it and be like, "That seems a lot easier than whatever the definition of a unicorn is now.” WHY ARE MORE PEOPLE NOT DOING IT THIS WAY?!?!?!?!

RB2B is becoming a less-than-one-man machine. 3 people $8.4M ARR And for the next 7 months, almost none of us are touching it. Tate (CTO) gets one day a month for dev work. Robb gets 30 minutes a day on escalated tickets. I post on LinkedIn 3 times a week. That's the entire human footprint on the business. Last year, we let AI run it for 7 days, and it worked… …so now we're doing 7 months. If the bet pays off, an $8.4M ARR SaaS basically runs itself while we build something new from scratch. If it doesn't, I'm completely delusional, and you get a front row seat to watch. Either way, my livelihood is on the table.

Founders think the biggest risk of taking VC money is running out of cash and going bankrupt. It's not. It’s being chained to something that LOOKED promising for a decade. The decisions you're forced to make are tied to the money you took and what you said you'd do when you took it. If you just raised $20M saying you'd spend it in 18 months and burn a lot of dough... you can't read one of my posts and say "Now I'm going to run a profitable business." That’s not how this works. Your reputation is the most important thing. You have to fulfill the promises you made. So go for it. Really f*cking go for it. But part of really going for it is accepting that if it's not working after you really tried, folding and going to do something else is part of it. That's what your investors expect you to do too. This is the trap I'm always warning founders about. It's not the catastrophic blow-up you should be worried about when you take VC. It's being stuck in something - FOR A DECADE OR MORE - that looked like it was promising but actually wasn't. Don't have too much pride to fold something that isn't worth your time. Because the upside of something that IS worth your time is so much greater than you realize.

@kennandavison YES. This is a massive win for you (obviously ha) and Founders should take note of something important The fact that you couldn't get the series B created a much higher probability life-changing outcome ... w/ that B, $105 isn't enuogh And $500 or whatever is WAY harder

Skio just sold for $105M cash at close on $8M raised.

Link to the episode: youtube.com/watch?v=hUUl2c… And also, if you found this useful: 1. Follow me @RetentionAdam for more on bootstrapping and building in public. 2. Repost the tweet below to share this with a founder who needs to see it.

B2B organic traffic has been down 40% in the past year. But it’s not hitting everything equally. Certain types of pages are getting hit way harder than others… …and according to Gaetano DiNardi, the pages dying fastest are the ones most SaaS companies are still building: > Glossaries > FAQs > "What is X" definitions These are the things that can be usurped by AI and just explained in an answer. There's no need to click through to a SaaS website to get the answer anymore. You can still rank number one in classic search positions. And LLMs will scrape, summarize, and steal your content…then recommend your competitors instead of you. It's a statistical lottery mechanism. The more your brand gets associated with a thing, the more likely LLMs are going to arrive at a consensus. When people talk about revealing anonymous website visitors, RB2B comes up so much that if you don't mention us, you're going to look like you don't know what you're talking about. I sat down with @gaetano_nyc - principal consultant at Marketing Advice, on my podcast to break down the full playbook. Check it out below: