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: 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...
Dear SaaStr: Is It Ridiculous To Call Yourself the CEO When Your Startup is Tiny?
Dear SaaStr: Is It Ridiculous To Call Yourself the CEO When Your Startup is Tiny? I used to feel that way, at least a bit. I used to look at tiny little startups and wince when a founder went around talking about himself as “CEO”. But then I had to learn how to Sell...
Dear SaaStr: What Did You Do in Your Startup That Didn’t Scale?
Dear SaaStr: What Did You Do in Your Startup That Didn’t Scale? My list is a bit quirky, but perhaps it will help a few others to accelerate — or drop — a few things: Doing international customer support myself. For months, I did European customer support myself...
Dear SaaStr: What Are Some Lies Founders Tell Themselves?
Dear SaaStr: What Are Some Lies Founders Tell Themselves? #1 Lie. That it will get easier. It never gets easy, but it can get less difficult: You get better. You constantly learn, and in not that long of a time, become one of the experts in your space. At some point,...
Dear SaaStr: As a Founder, How Do You Deal With Stress In a Startup?
Dear SaaStr: As a Founder, How Do You Deal With Stress In a Startup? Dealing with stress is important, especially for founders, who do have to hide … some of it. Per the WSJ and Challenger, Grey, this year more CEOs have left their jobs than any year since 2002...
Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do?
Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do? Listen. It usually means something is wrong. Or at least, off: If you got the equity splits right at first, usually, big issues don’t come up later. This may be a sign you need to...
Dear SaaStr: What’s Your Top Advice For All New B2B Founders?
Dear SaaStr: As a VC, if you could go back to your operational experience (as part of a hyper-growth startup), then what would you remind yourself to take note of? My top list: Slow down big decisions — when you aren’t sure. You have to move fast and break things, but...
Dear SaaStr: My Startup is Nearing The End of its Runway – and I Found Out My CEO Has Been Taking Money from the Company. What Should I Do?
Dear SaaStr: My startup is nearing the end of its runway – and I found out my CEO has been taking money from the company. What should I do? Unfortunately, this is a little more common than you think. Maybe even more common today than a few years back, as VC...
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