Why Your Startup Will Fail, If It Does Fail: The Drama Inside, Not Outside
The brutal truth about what actually kills high-growth companies I’ve now been involved in 100+ B2B startups as an investor, advisor, or founder. I’ve watched companies go from $0 to $1000M ARR. I’ve seen unicorns born. And I’ve seen what...
4 Reasons to Send Investor Updates Even When Times Are Tough
Founders: I know it seems like on X everyone is killing it, massively rounds, AI this, AI that. But if you aren't killing it … 😢Not sending investor updates is not the answer Investors expect tough times. They may be critical, but they expect it. But...
Dear SaaStr: For High Dollar Vertical SaaS, Does The VP of Sales Need Domain Expertise?
Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? This is the scenario when...
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...
The #1 Clear Sign a VP Will Fail. Be Honest With Yourself When You See It
I’ve seen it again and again across 30+ investments, 10+ unicorns, and hundreds of portfolio company board meetings. There’s one pattern that predicts VP failure better than anything else I’ve seen. Not their resume. Not their pedigree. Not even...
Dear SaaStr: How Did You Get Your First Major Customers?
Dear SaaStr: How Did You Get Your First Major Customers? Secret here: every story is different. In my first start-up, it was pure hustle. We had a concentrated number of high dollar customers, so I did “outbound”. I found the right decision makers, got on the phone,...
Stop Building Financial Plans on Hope and Prayer: Why Your C-60/C-90/C-10 Planning is Backwards
I see this pattern every single financial planning season. I’m seeing it right now. And honestly, it drives me absolutely crazy. A founder shows me their plan for next year. It looks reasonable at first glance. Growth targets seem achievable, albeit a bit aggressive....
Dear SaaStr: How Many Options Should I Give to the First Non-Founder Employees?
Dear SaaStr: How Many Options Should I Give to the First Non-Founder Employees of they are making below market but non-zero salaries? Here’s the tough part. It’s really hard. What you should do is give them say 3x their forgone salary in stock — 3x to account for...
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: 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...
CEO & Founder
Related Posts
