RB2B

What does the CEO of a $25m+ ARR business (RB2B + Retention.com) ACTUALLY do all week? I’m not sure what most other CEO’s do, because this is my first at bat… But here’s what I do. I drop my daughter off at preschool on an ebike at 8:15. Get to the office at 8:30, and leave every day around 5:30. I don’t work outside of those hours, or on weekends, but during those hours, there is not a wasted SECOND. MONDAY: INTERNAL MEETING DAY - 1 on 1s with Robb, Tate, Keleigh, Diana - 90min L10* (exec team), 60min L10 (RB2B) - 1h LinkedIn idea meeting with Alec - 15-30min with Taylor (email) and Ali (ads) TUESDAY: CONTENT DAY - 1h UnF*ck My Startup LIVE - Write 3 LinkedIn posts (ideally) - Record 1 YouTube video (Samu writes script) WEDNESDAY: CUSTOMER CALL DAY - 1-4pm CDT: 15min customer calls - Morning - other zoom calls/other work THURSDAY/FRIDAY: WHATEVER DAYS - Zoom calls/other work - Write posts (I usually don’t get my 3 LI posts Tues) - I go to 1 YPO forum meeting/mo (all day thursday) - I do a 1-on-1 with jonathan (exec coach) biweekly - We do quarterly exec offsites that require travel What are zoom calls/other work? - Writing posts I didn’t get done on Tuesday - Working on product, or marketing copy for the site - Calls w/ Robb and Tate about reinventing RB2B - Calls w/ Phil about Retention 2.0 - Calls w/ super-smart people about content/virality - Calls w/ industry people trying to figure it out - Calls w/ whatever crazy experiment I’m doing that Q (most fail) - I also love meeting people in the mornings for sauna/cold plunge *we run EOS at our company, an L10 is a meeting format. TAKEAWAY I do not know this for a fact … But my sense is that other $25m ARR CEOs will look at this and say it’s a joke. That I’m not grinding enough. I’m not hustling enough. Trying hard enough. Ambitious enough.  That may be true. My response is this: I’ve been at this game in one way or another for 11 years… I look at this calendar and I think: “I could do this for another 30 years”. And guess what… If I can? This thing will be a colossal, epic success. And in the meantime... I’ll just keep building.

Does Adam Robinson look for AI tools to automate his business or does he build his business SPECIFICALLY so it can be automated by AI? 👀 The answer may surprise you. 😮 He digs into this on his recent Startups Decoded podcast appearance with Andy Walsh: https://lnkd.in/d9_st2zf

So Adam Robinson let AI 🤖 take over RB2B for 7 days. 😬 Was a complete and unmitigated disaster? 👀 Here's what happened: https://lnkd.in/giHS2UtZ

Retention.com & RB2B grew 1.2% in Sep ‘25 to $25.6m ARR. RB2B grew 5.6% to $6.3m ARR and Retention shrank 0.7% to $19.5m ARR. Here’s the good, bad, and ugly that happened last month: GOOD: - RB2B hit $6m ARR on Sep 3, WHOOP! - RB2B did not blow up when all 3 FTE went off the grid for a week and AI ran everything - We had a GREAT in-person AI hackathon with both teams in NYC - We are working on re-inventing R!.com in a way that I am incredibly excited about, led by Phil Roselli - We about to drop a Person-Level Identity API - provide an IP/useragent and get back an email/biz email/biz profile BAD: - Unfortunately our core R! business is still stuck (but we’re working on that as we speak) - I am deathly afraid of reinventing RB2B, even though it is totally obvious what needs to be done - because there is something magical about the current simplicity of it … so we keep putting it off - Only generated $799k of cash this month (6mo rolling average was $1.1m last month) UGLY: - Maybe I’m looking through rose colored glasses but I see no ugly. ——— I stopped posting about Retention.com for a while because I thought it was distracting from the focus of RB2B and its top-of-funnel. Apparently some of our prospects on that side of the business now think that company is only at $6m and has a team of 3… And people on the B2B side don’t realize that I have another business, or that the combined scale is in the mid-20’s ARR. So there you go. Full business update. ——— I haven’t been as excited about our business as I am now for a long long time. RB2B is exciting because we’re showing you how far you can get in 2025 with a combination of a Founder-Led Freemium GTM, entirely AI customer interaction, and a tiny core team. (We’re shooting for $7m ARR by year-end and $10m ARR year-end 2026, with 3 FTE!) Retention is exciting because if this product reinvention works, we’re incredibly well positioned to experience another S-curve of growth in the Shopify ecosystem. TBD there … but we’re seeing very encouraging signs. ——— I was speaking to a founder friend this morning about how when you’re really excited about your business, everything else in your life is so much better. It’s an energetic tailwind. The same is true for the other way … When things suck (and they have for us, many times)…. It’s a cloak of anxiety that’s impossible to get out from under. But man… What a gift - to have something so interesting and dynamic to work on every day. And with such talented people. Entrepreneurship is truly the greatest, most interesting game in the world. The sad thing is that some day the music will just stop. For me, for my biz, for you, for all of us. At that point, I’m only have one regret… That I couldn’t just do it all over again. So I’ll just keep building.

In the last 30 days, I’ve spent $10k on LinkedIn, Meta, and YouTube re-targeting ads. We've driven 205 signups, but we have a problem. Trials aren't converting to paid users (yet). Here’s what went wrong, what’s working, and how we’re fixing it: First, a channel breakdown: META (LAST 30 DAYS) - 176 trial signups - $20-68 per signup - Broad campaigns: $21 per signup - Minimal script installs LINKEDIN (LAST 30 DAYS) - $3,041 spent - 22 conversions at $138 each - 7.18% CTR PERSONA BREAKDOWN - Sales Persona: $819 spent, 0 conversions - Founder Persona: $822 spent, 12 conversions at $68.56 - Marketing Persona: $600 spent, 3 conversions at $200.30 - Outbound Agency Persona: $797 spent, 7 conversions at $113.98 GOOGLE/YOUTUBE (LAST 30 DAYS) - $2.8k spent - 143,599 video views - 7 conversions - Pure retargeting play WHAT’S WORKING - Broad Meta campaign at $21/sign up - LinkedIn Founders at $68 conversions - LinkedIn CTR at 7.18% (industry avg is 0.5%) WHAT'S NOT WORKING - Meta’s finding signup collectors, not users. We’re optimizing for trial starts when we need script installs. - LinkedIn Founders are converting at $68 but Sales Persona spent $819 with zero conversions. THE FIX: We're using Understory to run our ads. I love working with Ali Yildirim🌲 and Alex Fine🌲. The issue, they argue, isn't the ads themselves, but the conversion event they are optimizing for. Right now, Meta is finding people who simply start a trial, not those who become paid customers. I think this is a HUGE PROBLEM many SaaS companies face. They run ads, they get signups, but they don't convert to revenue. That's why I asked the Understory team to join us on Unf*ck My Startup LIVE tomorrow (12pm PT) and share their entire solution and reveal the exact next steps they are taking to fix this in real-time. This is can't miss for any founder or marketer running paid campaigns who needs to turn high-volume sign-ups into predictable, recurring revenue. Join us here: https://lnkd.in/gs-Yyc4p P.S. If you want a copy of our Paid Media performance reports, comment REPORT below and I'll send you an interactive and uncensored copy. Shows you RB2B campaign and channel breakdowns by impressions, clicks, spend, creative, and ad type. Use it to benchmark your ad program.

Did Adam Robinson fire everyone and let AI run this whole company? 🤯 Well... sort of. He did hand it over to the 🤖 for a whole week. 😮 How did it go? Check his latest video to find out: https://lnkd.in/giHS2UtZ

Building in "stealth mode" is the DUMBEST thing a startup founder can do. Here are the top 6 reasons why building in stealth mode is a rookie mistake (and why I won't sign your NDA): 1. No one is going to steal your idea. Anybody who is capable of executing your idea is already busy doing something else that they believe is more valuable than whatever you share with them. Don’t make people sign NDA’s to talk to you. It makes it clear that you don’t know what you’re doing. 2. You NEED feedback. People farther along in their journey can often help you avoid mistakes that all entrepreneurs make (and you will make, too!). More importantly, you need to be speaking to your ideal customer profile to figure out if your product is even valuable. 3. Ideas are like assh*les. Everybody’s got one. Furthermore, this is hard to believe, but someone is definitely working on whatever your idea is already (if it’s even a halfway-decent idea). That’s just the world we live in. 4. Ideas are just multipliers of execution. Jeff Bezos and Elon Musk created trillion dollar companies through being the best at execution. Many others had the ideas of online bookstores, electric cars, and rich guys have been trying to go to space (unsuccessfully) forever. A great idea makes great execution go even faster, but is worth nothing on its own. 5. Building in stealth increases the risk of your startup to a point where you will almost certainly fail. Please read “Four Steps to the Epiphany” by Steve Blank. The ONLY shot a startup founder has is to follow the method in this book. You must be developing the customers for your product simultaneously with the product itself. If no one will buy what you are building, you must stop and start over. The sooner you find out the better. There’s no way to find that out in “stealth mode”. 6. Our intuition is a terrible indicator of market viability. You simply have no idea what the market is going to want, with the one exception of you building something to solve your own problem. However, that is still a market of one, and you need to go out and validate that others have the same problem to even have a SHOT at succeeding. TAKEAWAY: Don’t build in stealth mode. Go get feedback from your ideal prospects. Talk to founders who are more experienced than you. Build up your customer base before you start building your product. Read “Four Steps to the Epiphany”, and treat it as Gospel. But please, pretty please, above ALL ELSE… Don’t ask me to sign an NDA to hear about your “idea”.

There's more than one way to RB2B? 🤔 How you set it up can make all the difference. 👀 Adam Robinson breaks it down on his new YouTube series here: https://lnkd.in/g4g7TZvP

So wait... if you take VC money, you have to give it back? 💸 Is this the sneaky truth that Josh Abramson, co-founder of Vimeo and CollegeHumor learned on his founding journey? 🤫 Adam Robinson has even one more reason to be smug about it on the most recent Unf*ck My Startup with Pete Crowley 💡: https://lnkd.in/gWnUqf5J

Is it better to get rich every day or make a bet on "maybe someday"? 👀 According to Adam Robinson, that's bootstrap vs. VC in a 🥜-shell. He goes toe to toe with Josh Abramson, co-founder of Vimeo and CollegeHumor and debates on the most recent Unf*ck My Startup with Pete Crowley 💡: https://lnkd.in/gWnUqf5J