Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers for a Startup? Yes — at least at first. Especially if you haven’t done a lot of sales yourself. Boy, sales is hard. It’s being told No a lot. It’s having literal, or virtual, doors shut...
Dear SaaStr: How Should I Design a Sales Reps Compensation Plan at Just $10k MRR? Figuring out your very first sales comp plan when you don’t have a repeatable process or much revenue is confusing. I was exactly in the place you were (first rep at $10k MRR) and...
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,...
Q: I’m a startup founder weighing multiple VC term sheets at similar valuations. How should I choose? My force-ranked list of criteria: #1. Who do I truly trust the most? This doesn’t mean who is the “best guy”, or smiley-est, or nicest. In fact,...
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. I can tell you I never skimped on my own vacations as CEO — except in the first year of my second start-up, when for a while I...
I suspect we’re about to see this chart for 4 year degree completion as well https://t.co/fX7vqmIKqp — Dylan Field (@zoink) May 3, 2023 It’s not a myth, but I think the reasons for it are confusing. Yes, Mark Zuckerberg, Bill Gates, Aaron Levie of Box, etc....
Dear SaaStr: Does Bootstrapping Through an Agency/Services Business Work? Running two businesses at once well is really, really hard. But I think if you are thoughtful about it, using an agency/services business can be a viable way to bootstrap your way into a SaaS...
Dear SaaStr: How Difficult is It To Fundraise Over the Summer? There’s still seasonality to venture fundraising, even now with so much being done over Zoom. Yes, deals get done every day in venture. But especially in bigger partnerships, it’s just harder...
Dear SaaStr: How Many Board Seats Do VCs Typically Get? Let me try to simplify, generally speaking: 1. Generally, “proportionate” boards are usually seen as fair, and easy to agree to. I.e., if the investors own 20%, and founders 80%, then investors get 1 board seat,...
"Bootstrapping wasn’t a magical choice for Mailchimp. No one would fund them."https://t.co/I0X6sJVY5t — Jason ✨Be Kind✨ Lemkin (@jasonlk) May 22, 2023 Dear SaaStr: If you started a new company today how long would you be bootstrapped for...
Q: How do VCs pick which seed investments to make? There is one common factor, that founders know, but often lose track of in their pitch: every VC, at any stage, is looking for outliers. No matter the price or how early or late. Your pitch, your team, your metrics,...
Dear SaaStr: How Do You Overcome “Stage Fright” as a First Time CEO? Don’t worry about stage fright. It’s real. I used to have it. And … you’ll get over it. I remember the very first time I had to present to a Fancy Board Meeting. I wasn’t a...
Dear SaaStr: How Can a SaaS CEO Tell Which Customers are 10+ Year Customers? I think it’s fairly easy. Look for: Are they running an entire division or group (or more) on your product? Is the use case mission critical — even if niche? I.e., would the business be at...
Very few downsides to getting to know the CEOs of your competitors — Jason ✨Be Kind✨ Lemkin (@jasonlk) May 13, 2023 Dear SaaStr: Suppose the CEO of my competitor contacts me, interested in acquiring my app (privately owned). What steps would I take to avoid...
Dear SaaStr: When Searching for a Co-founder, How Do You Know You Found The Right One? I think it boils down to 2 key factors: Someone that is both very good at, and better than you, in several key functional areas. If you are good at coding, she is good at sales and...