Dear SaaStr: What Was Your Biggest Early Days Mistake In Your Startups? Boy it’s tough to pick just one mistake. But I’d have to say in both my startups, the biggest mistake was not taking the time in the beginning to get the founding team right. This is tough. You...
So I have a ton of empathy overall, but burnout? Sort of. I do have empathy for founders, execs and ICs that truly left nothing on the field for 3, 4, 5 years. That truly burns you out. But even there, my empathy has limits. Because while it’s real, you gotta...
Dear SaaStr: Does Anyone Regret Being an Entrepreneur? No, but there are … laments. The thing is, successful entrepreneurs generally speaking, can only do that — be successful entrepreneurs. Why? Why can’t they go work for someone else, collect a huge paycheck,...
As we gear up for 2024 SaaStr Europa in June in London and 2024 SaaStr Annual in September in SF Bay Area, we’re taking a look back at some of the top sessions from years past. Tomasz Tunguz, now Managing Director of Theory Ventures (and then MD with Redpoint...
Dear SaaStr: Should I Go Into SaaS Sales? If you aren’t sure you want to go into sales — don’t do it. Maybe in 2021, when many SaaS leaders were growing at simply unprecedented rates, could succeed in sales if you weren’t sure you wanted to sell. Not today. A...
Dear SaaStr: Why Would I Start a Startup if I Only Have a 5% Chance of Succeeding? Don’t do it. If you only see a 5% chance of succeeding, don’t do it. With both my start-ups (maybe three, if you count SaaStr and SaaStr Fund) … I was 100% sure we’d succeed. And I was...
Dear SaaStr: Do You Have To Be Rich To Join a VC Firm As a VC? No, you do not. This is a common misunderstanding. It may even be a negative to be truly rich when you join a VC firm. First, you do have to invest a lot of your own money to be a true partner into the...
Dear SaaStr: What Advice Do You Have For a First-Time VC? My advice is hard learned, and pretty contrary to what you’ll be told. YMMV. So many mistakes you'll look back in VC But the #1 you'll probably regret was letting those founders leave the room,...
Dear SaaStr: Does Everyone Lose Most Of Their Friends on The Entrepreneurial Journey? You will lose friends on many levels if you build a successful start-up. First, if you co-found a company with friends, it’s likely one of them won’t go the distance. And it’s likely...
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. It is incredibly hard to figure out how to replicate the magic of...
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 Has Been Your Biggest Career Mistake? Maybe not slowing down just a little bit. The week in my first real professional job when I realized I’d been there long enough and had nothing left to learn … I walked in and quit that day on the spot. I had no...
Seth Shaw was most recently CRO at Airtable, and before that, CCO at Invision and VPS at Wrike. He was one of the early sales leaders managing a distributed sales team, and it’s interesting to look back at his 2019 talk at SaaStr on just how hard it can be...
Dear SaaStr: Do Salespeople on Commission Really Sell More Than Salary-only Salespeople? 1000000000000.00% in SaaS. Commissioned salespeople sell more. Lots of us try to run this experiment. At least, those of us who haven’t done software sales before, and have a...
Dear SaaStr: What Were Your Toughest Times Before Breaking Out? My toughest times: COO pulling out after signed term sheet — VCs then pulled term sheet. This of course was my fault — I hired the “wrong” COO. But boy it was tough. I had 9 employees on payroll and $0 in...