Dear SaaStr: Is It Worth Working as a Sales Rep?
Dear SaaStr: Is It Worth Working as a Sales Rep? Absolutely. Being a sales rep is the hardest job that almost anyone can get and at least try to do. But boy, you will learn. You will learn: How to hear “No” 100 times in a row. If you can turn 100 “No’s” into 1–2...
What To Do When A Customer Wants to Cancel A Contract
Hopefully, 100% of your customers love you. But as time goes on, you’ll oversell a few deals. Or not quite deliver in some fashion. Or fail to deploy in others. And some customers will ask for their money back. When they e-signed binding, good old-fashioned...
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated?
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated? The part I didn’t originally get as a first-time B2B founder was how relatively easy it is to grow exising accounts and account size if your customers are happy. 120% NRR: Your revenue...
Dear SaaStr: What Do You Do With Churned Customers?
Dear SaaStr: What Do You Do With Churned Customers? You put them into a Get Them Back bucket and re-market to them with a dedicated program. And you have sales especially follow-up twice. Once in about 90 days, to see if they might want to come back —...
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that...
Dear SaaStr: When Bootstrapping a SaaS Product, What Should You Be Aware Of?
Dear SaaStr: When Bootstrapping a SaaS Product, What Should You Be Aware Of? Just a few observations from bootstrapped B2B companies I’ve had some involvement with: It probably will take 1–4 years longer to get to $10m ARR or so. I don’t fully have the data to support...
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t?
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t? First, does your highly-funded competitor have a dominant brand yet? If not, it may not matter. There is no “winner” yet. The #1 brand trumps capital. But if they have...
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup?
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup? My Top 5: It will take you at least 24 months to really get anywhere. Everyone mentally budgets 10–12 months. It’s never enough. At least, not to get enough paying customers from Code...
Dear SaaStr: I Sold My Company And Made Real Money, But I Still Feel Like A Loser. What Should I Do?
Dear SaaStr: I sold my company five years ago and have built a net worth of ~$10 million, but compared to my friends I feel like a loser and still keep trying hard at startups that stress me out and make me miserable. What should I do? It’s crazy, but …...
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth?
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth? My uber-learnings: Find the best boss you can; and Take on every initiative, project, task, and endeavor you possibly can from her. And work for them for a while. Long enough to get promoted once,...
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product?
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product? Roughly — only for as long as it’s about a 10-hour a week job. Or often, maybe only up to $3m-$5m in ARR or so. These days, especially, I see way too many B2B companies at $8m-$10m ARR or beyond...
Dear SaaStr: How Much Vacation is Normal for an Early Stage Startup CEO?
Dear SaaStr: How Much Vacation is Normal for an Early Stage Startup CEO? I’ve gotten worse at this. I think many of us have. 996 matters as founders. The pace of change, the scale of competition, is like nothing we’ve ever seen before now, in the Age of...
Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Should We Listen to Them?
Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Should We Listen to Them? In my experience, about 66-70% of the time this is bad advice, especially if it is coming from a Very Large VC. Not always — but more often than...
Dear SaaStr: What Were the Biggest Mistakes You Made Getting Your Startups Going?
Dear SaaStr: What Were the Biggest Mistakes You Made Getting Your Startups Going? The biggest two mistakes I made, I made twice, maybe thrice. They were: One, starting with too incomplete a management team. In my first start-up, while the core 3 co-founders were...
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