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This is my playbook for bootstrapping an AI agent business to $9M ARR. The most important thing is that you need something repeatable and scalable, something where if you do more of, you get more money. You need the equation where you can arbitrage every dollar you spend into more dollars on the other end. Here is how you get there: 1. if you're in B2B, just do the B2B stuff. self-serve is very hard to make work in B2B. it's so much easier to build a sales team, teach them the product, and let them sell it, instead of building a very intuitive platform and hoping people figure it out. that's why all these bigger companies are mainly doing "book a demo with us." they charge customers a lot more because there's no public pricing, and they can set the product up for them. you cannot rely on a middle manager at a non-tech company to put in the effort to use your platform, even if it's extremely intuitive. if you're bootstrapping, you can't hire a sales team on day one. so you need momentum from self-serve customers first. but the goal is to layer in sales as fast as possible, get on demo calls, set up the product for bigger customers, and invest in building an intuitive platform at the same time. 2. content is non-negotiable, even if you're sales-led. good content gets you brand visibility and brand awareness, and that makes all the other channels work much more efficiently. paid ads work much better if people recognize your brand. if they click on your page and see content that people are engaging with, good quality content, it compounds everything. here's what that looks like: video: it depends on your ICP, but we all know video is hard to do, and that's a good thing because it makes the barrier to entry much higher. you can signal that you are a serious business if you do good quality video content. be creative within video, but don't get too creative with the kinds of videos. the kinds of videos you should be doing are product videos and customer videos. that's it. you can be creative in telling your customers' story, you can be creative in launching a product, but don't do the stunt thing, the office content, the random skits. they can work, but you only do them after you do the things that you know will work. hire a videographer in-house. agencies are so expensive (this is just a good rule of thumb). text + personal brands: you need personal brands for everyone in the company. EGC (employee-generated content) needs to be a non-negotiable. everyone on the team posting at least twice a week. 3. warm outbound is the lowest-hanging fruit. warm outbound = outbounding people who have already seen your product. people who interacted with your LinkedIn posts. people who visited your site but haven't signed up. people who created an account but never finished onboarding. these people are the lowest-hanging fruit. email them, call them, put them in a sequence until they become customers. you can have very clear KPIs for your team on this. 4. cold outbound, if your ICP is big enough. be good at writing cold emails and managing your own infrastructure. don't go through an agency. build a system where you can send emails profitably. if it works, send more. if that works, send more. scale it until it doesn't make sense to continue. also do this in-house if it's an important channel. 5. SEO and AEO are extremely important. whenever I want to try a new product, I ask Claude. AI search is a non-negotiable channel now. you need to show up there. that means a lot of Reddit, a lot of review websites, a lot of talking to blogs and backlinking sites to make sure they write what you want with the messaging you want. 6. expansion: be friends with your biggest customers. get on a call with them. know them by name. they need to have your number. they need to be advocates for you. build community around the customer. a lot of founders do not see their customers as friends or a community. they just see them as revenue. that's so bad. your customers need to enjoy spending time with you and talking with you. 7. pricing is the fastest lever. you need to find a good sweet spot for packaging and pricing. incentivize people to spend more money and make sure it's a good deal for them. there's no shortcut, you talk to customers, see what they care about, see what they get a lot of value out of, and capture some of that value while making sure they're successful. 8. margins don't matter early on. if you have a $10M ARR business but you spend $10M to run it, that's fine. you can always cut costs. revenue is the most important metric. it's easier to cut costs than to make more money, so in the beginning, focus on making more money. That's how we built @chatbase to where it is today. Most of this will continue to scale with us as we go to 100M ARR.
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Quick Insight
This is a comprehensive B2B SaaS playbook from someone who actually scaled an AI agent business to $9M ARR. The key insight is prioritizing sales-assisted onboarding over pure self-serve for B2B, plus treating content and warm outbound as force multipliers rather than optional nice-to-haves.
Actionable Takeaway
Start tracking and reaching out to warm leads for his side projects — people who visited landing pages but didn't convert, engaged with posts about his tools, or signed up but never completed onboarding. Build simple email sequences for these audiences before investing in cold outbound.
Related to Your Work
The fintech platform could benefit from the sales-assisted approach rather than pure self-serve, especially for larger merchant partners. For side projects like print-on-demand automation, this validates focusing on direct customer contact over building "intuitive" self-onboarding flows that mid-market customers might abandon.
Source Worth Reading
Single tweet, no additional links. The value is in the complete framework presented here.