The Zero to $10M ARR Newsletter I decided that since Iām bootstrapping Helply and InstantDocs in public, I might as well teach everything I know. So I'm starting a new community for B2B SaaS founders bootstrapping their companies to $10M ARR. It's called the Zero to $10M ARR Academy. If you're scaling something and want the actual playbooks on what, when, and how to do it, come join us. One of my VC-backed friends raised $33M. His startup got a $195M valuation in 2023. Every metric looked...
9 days agoĀ ā¢Ā 2 min read
The Zero to $10M ARR Newsletter This newsletter is brought to you by Elizabeth O'Neill, an executive coach (and my sister) who helped me through some of the toughest moments in my journey as a founder. Sheās not just family. We worked together for 4 years during some of the lowest points in my entrepreneurial career. Without her coaching, Iām not sure I wouldāve made it to 20 years in. We also sat down recently to talk about those 20 years on her podcast. Give it a listen. I think youāll...
16 days agoĀ ā¢Ā 1 min read
Hey Reader, Most AI agents fall short because the data behind them is weak. You donāt know what to train them on. Or you add what you have, but arenāt sure if itās sufficient. And thatās where it breaks. Itās a data source problem. When we set out to build Helply, that was one of our biggest findings; lack of optimized data was killing AI agents. We went out and solved that problem with Knowledge Bridgeā¢. Knowledge Bridgeā¢ runs your support tickets against your knowledge base, finds the gaps,...
25 days agoĀ ā¢Ā 1 min read
The Zero to $10M ARR Newsletter The Zero to $10M ARR Newsletter is powered by Helply. Helply answers customer questions 24/7 so you can focus on more important work. Join the VIP program and we'll guarantee 50% resolution rate in less than 60 days. $180K VP of Sales. Zero sales. $200K dev. No product shipped. My $2M lesson in hiring backwards. I burned millions trying to ālook like a real companyā: Here are some of the expensive hires that killed my runway: VP Sales ($180K base) when we had...
30 days agoĀ ā¢Ā 1 min read
Today, I walked the founder of a Y Combinator unicorn company through a fascinating a-ha moment. I was setting his company up in Helply and he discovered something most companies never find: A way to autonomously identify and fill knowledge gaps. Instead of the usual generic AI setup where you ācrawl your website and call it a day,ā something different happened. Helplyās AI: analyzed their support history identified 50 specific knowledge gaps and filled them systematically. For the first...
about 1 month agoĀ ā¢Ā 1 min read
The Zero to $10M ARR Newsletter The Zero to $10M ARR Newsletter is brought to you by Helply. Most support teams donāt realize it, but outdated knowledge bases bleed time and money. Helply changes that. Our AI auto-detects missing answers, updates content, and keeps your support accurate without the manual grind. No more endless rewrites or frustrated customers. Ready to see the gaps in your system? Book a call and weāll audit it live. No fluff. Just real insights. From LinkedIn message to...
about 1 month agoĀ ā¢Ā 1 min read
The Zero to $10M ARR Newsletter The Zero to $10M ARR Newsletter is powered by Helply, the AI support solution for growing companies. We help you scale support, deflect tickets, and cut costs while keeping customers happy. We are working hands-on with 100 companies to build, train, and launch AI support agents in just 30 days. Want in? Book a call now to join our VIP Slack program. Software engineering jobs just died. Not slowly. Not gradually. They dropped 70% in 18 months. Hereās the reality...
about 2 months agoĀ ā¢Ā 1 min read
The Zero to $10M ARR Newsletter The Zero to $10M ARR Newsletter is brought to you by Helply (the AI support solution built for growing companies). We help you scale support, deflect tickets, and cut costs, without sacrificing customer experience. We are working 1-on-1 with 100 companies to create, train, and deploy your AI agent in 30 days. To join our Slack VIP program book a call here (it's free). I was deep in the weeds, staring at our product roadmap, knowing we had a big challenge in...
about 2 months agoĀ ā¢Ā 2 min read
The Zero to $10M ARR Newsletter The Zero to $10M ARR Newsletter is brought to you by Helply. The AI support solution built for growing companies. We help you scale support, deflect tickets, and cut costsāwithout sacrificing customer experience (and without scaling costs). Join our VIP program and we'll help create, train, and deploy your AI agent in 30 days (at no extra cost to you). Only 100 spots available. Apply here. I turned down every VC check for 12 years to keep 92% ownership of...
2 months agoĀ ā¢Ā 1 min read