$19m ARR w/ 9 FTE - Early Plays @ RB2B & Retention.com

I just bootstrapped RB2B to $5m ARR in 13mo with 5 people. I also bootstrapped Retention.com to $13m ARR with 6 people. My secret? What I do is repeatable. Here’s my 7-step playbook to 7-fig ARR with tiny teams:

1. Validate demand before building ANYTHING

- Retention started as a feature in my first startup, Robly. People loved the identity feature but hated Robly, so we knew the demand was there
- RB2B is a B2B version of Retention. We did 300 discovery calls with marketing leaders to validate the market wanted person-level ID for ABM

2. Create a DIFFERENTIATED (albeit terrible) v1 of your product that people will talk about

- Retention was originally a batch spreadsheet of site visitors. Pretty terrible user experience, but it was so different that it got tons of traction
- RB2B is riddled with horrible problems to this day – but 1 year ago we were the only vendor who resolved site visitors to the person-level

3. Create MASSIVE AWARENESS… Through your HUMANITY

- The best way to accelerate word-of-mouth is through social. I did a crazy FB ads campaign for 6mo when we launched Retention. It stopped working, but EVERYBODY in our TAM saw them… That + word-of-mouth + cold email
- For RB2B I was able to create viral LinkedIn thought leadership to our addressable market for the 6mo prior to launch. We had a 3000 person wait list

4. Eliminate sales and onboarding friction

- At Retention, we gave our customers 25 free emails, then forced them to a call with Diana. She did thousands of 5min presentations that answered key questions and got people to do a 2mo paid trail, then upgrade (or drop)
- At RB2B, we did a freemium product to a PLG with a sales rep answering questions and helping with tactical onboarding for high-value users

5. Wait an unreasonably long time to hire ANYBODY

- At Retention, we had the same 6 people at $13m ARR as we did at launch
- At RB2B, Robb has managed to create an AI that supports 40k free users

6. Spend time and money on very few wildly positive ROI things

- At Retention, we had so few people that we had to focus on what mattered. Product, onboarding, cold email, demos, and “wow-ing” our customers
- At RB2B, we cut all paid marketing spend ($100k/mo) and our growth sped up

7. Keep doing steps 1-6 until you hit $10m ARR

- At Retention, not only did we not burn any money, we actually distributed $5m of cash to the co-founders on our journey to $10m ARR
- At RB2B, 12mo in and we are already profitable, with no plans to grow staff or spend on anything until $10m ARR

TAKEAWAY

Getting to profitability is the promised land for early-stage startups.

Yet VCs want Founders to raise money, usually to crash and burn.

I think more people should start startups my way.

If you can bootstrap $10m ARR, you can do ANYTHING you want with your life.

You will be making millions of dollars and playing by your own rules while enjoying total freedom.

I know because I’ve done it. That IS my life.

You can do it, too.