Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a B2B Startup?
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a B2B 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: What is The Biggest Pain for a CEO?
Dear SaaStr: What is The Biggest Pain for a CEO? Competition is stressful. Raising funding can be hard. Partnerships can be frustrating. But the hardest part is always recruiting. And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it...
Dear SaaStr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player?
Dear Saastr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player? You might not at first. So get help. But you’ll get better at this. As a first-time manager, you really won’t have the experience to know really who is an A, B or C player for any...
Five “Cons” To Adding a Free Edition
Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free can absolutely work. Done right, it’s built some of the biggest companies in B2B + AI: ChatGPT. Claude. Cursor. Slack. Zoom. Canva. Notion. Figma. Almost...
Dear SaaStr: How Do We Close Bigger Deals?
Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good VP of Sales that has sold at your “high end” price point. They will be much better at you...
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment?
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment? It’s OK — if it’s not too much. As long as the founders did everything they possibly could to make it work. Everything. And were honest. There are two types of losses for VCs...
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder?
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder? You first try to move them into an individual contributor role. If that doesn’t work, then move them out. This is one of the most frustrating outcomes, when a very talented co-founder becomes “unrealiable”....
Dear SaaStr: As a Co-Founder, How Do I Tell the Team I’m Leaving?
Dear SaaStr: As a startup founder, what’s the best way to announce your departure to the team and leave on good terms? The startup is series A/B, with 30+ employees. I have no magic insights, but I have transitioned post-acquisition out of 2 companies that...
How Much Equity to Give Your First Employees: The Real Data from 50,000 Startups
One of the most common questions I get from seed-stage founders: “How much equity should I give my first hires?” It’s a high-stakes decision. Give too little and you can’t attract talent. Give too much and you’ll regret it by Series B...
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: When Should You Sell Your Startup?
Dear SaaStr: When Should You Sell Your Startup? Having been through the acquisition process 4x — twice as a founder, twice as a start-up exec, here’s my list of when and if to sell. Don’t take it literally. Most startups never get a single good...
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...
The Top Reasons I Saw CROs Flame Out This Year
I saw about 10 CROs leave or get fired this year across the startups I work with or have invested in at SaaStr Fund. That’s a lot. That’s actually a ton. It may be a record. I suspect it is. And look, some CRO transitions are natural. The company...
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