Dear SaaStr: As a Founder, When Did You Realize You Were Limiting Your Company’s Growth and Success?
Dear SaaStr: As a Founder, When Did You Realize You Were Limiting Your Company’s Growth and Success? As we approached $10m ARR, we were doing very well: growing 100%, cash-flow positive, with 100%+ NRR. But I did see that certain of my weaknesses still were...
Dear SaaStr: What’s The Most Influential Piece of Feedback You’ve Received From a Boss or Coworker?
Dear SaaStr: What’s The Most Influential Piece of Feedback You’ve Received From a Boss or Coworker? My list: “You need to start managing people.” My second boss was generous enough to give me a small team to manage a few months into my job. I didn’t ask...
Dear SaaStr: What Risks Do Limited Partners in VC Funds Face That General Partners Do Not?
Dear SaaStr: What Risks Do Limited Partners in VC Funds Face That General Partners Do Not? Limited Partners or “LPs” are the folks that give the VC partners (the “General Partners”) the actual money to invest. There are many types of LPs, but...
Dear SaaStr: If You Just Received a $10m-$15m Funding Round, What Should You Actually Use It For?
Dear SaaStr: If You Just Received a $10m-$15m Funding Round, What Should You Actually Use it For? If you’ve raised $10m-$15m, I’m assuming you are somewhere between $2m and $10m in ARR (revenue). The most important thing you can do at a high level is to go hire Great...
Dear SaaStr: How Hard is it For a Startup founder/CEO to Settle Into a non-CEO Role After an Acquisition?
Dear SaaStr: How Hard is it For a Startup founder/CEO to Settle Into a non-CEO Role After an Acquisition? It is tough for most of us. We get that the bureaucracy and frictional taxes are going to go up. But it’s seeing the organization make decisions that are...
Dear SaaStr: What Are Some Things That Make a Founder Look Naive?
Dear SaaStr: What Are Some Things That Make a Founder Look Naive? A few in my experience: Mocking the competition, especially successful competition. The best founders do win, but they also profoundly respect the competition — and understand and learn from them....
Dear SaaStr: Should I Call Myself a Owner, Founder, or CEO?
Dear SaaStr: Should I Call Myself a Owner, Founder, or CEO? CEO. Although, perhaps say it in a neutral tone, with no bravado. I always thought the title was a bit silly when running tiny start-ups. But I missed an important point: Customers, Prospects, Recruits and...
Dear SaaStr: Why Do Great Employees Get Fired?
Dear SaaStr: Why Do Great Employees Get Fired? I’ve hired a lot. Lost a bunch, but fired very, very few. But I’ve watched some tough ones, some truly potentially epic talent get fired. This seemed to happen for two different (though related) reasons in...
Dear SaaStr: What is The Best Way to Hire Your First Sales Rep?
Dear SaaStr: What is The Best Way to Hire Your First Sales Rep? I’ll tell you the trick. It’s going to sound simple, but it isn’t, because almost everyone gets it wrong. For at least your first few reps: hire someone >>you<< would buy >>your...
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 Are Some Best Practices for Selling a New Product Into Existing Customers?
Dear SaaStr: What are some best practices for selling a new product/service to your existing SaaS clients? First, make sure your NPS is high. And drive it even higher. Here’s the bottom line: if your NPS is say > 40 or so, a significant portion of your customers...
Dear SaaStr: Why Are So Many CEOs Former Engineers, or At Least Have Technical Backgrounds?
Dear SaaStr: Why Are So Many CEOs Former Engineers, or At Least Have Technical Backgrounds? I’ve come to almost exclusively invest in founder-CEOs that are engineers. Or at least where the co-founder CTO is a true equal partner to the CEO. Why? Well to get something...
Dear SaaStr: Should We Drop Customers That Complain Too Much?
Dear SaaStr: Should We Drop Customers That Complain Too Much? Sometimes, yes. But just as often, the ones that complain are the ones that care. And oftentimes, their complaints help focus you on the gaps you really do need to fix. One thing most SaaS companies get...
Dear SaaStr: What’s The #1 Way to Motivate a Sales Team to Sell More?
Dear SaaStr: What’s The #1 Way to Motivate a Sales Team to Sell More? The best motivation for salespeople is seeing other salespeople at the same company making a ton of money. This: Proves (x) it can be done — even when sales feels hard, and Challenges everyone...
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