Dear SaaStr: What Are The Best Strategies for Raising Capital if Your Goal is To Get Acquired?
Dear SaaStr: What Are The Best Strategies for Raising Capital if Your Goal is To Get Acquired? Well, first, let’s be clear — it’s tough if your core goal is to get acquired for a big price in most cases. There really aren’t that many good...
Dear SaaStr: What is Your Worst Memory as an Entrepreneur?
Dear SaaStr: What is Your Worst Memory as an Entrepreneur? Let me make a short list: Having a critical co-founder walk out the door and never return. This happened to me once with a true co-founder, and once with a critical early employee (a critical COO). The...
Dear SaaStr: What Are The Biggest Challenges For a Non-Technical Founder?
Adding enough value in the beginning. If you can’t build it, can you: Sell it? That’s worth it. If you can bring in all the first customers, that’s a magical skill. Design it? Head of Product is just as important as Head of Writing Software. Sometimes, one person can...
Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup?
The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least. But the toughest personal challenge for...
Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder?
Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder? The list of problems is endless (this is one of the hardest parts of the job), but let me try to order a few of the biggest challenges roughly based on stage: Top issues you face as a startup,...
The #1 Worst Hire of All When You Are Just Starting To Scale: The Mediocre VP of Engineering
Every time I see a CRO that doesn't sell themselves, they fail. Every time I see a CTO that doesn't code themselves, they fail. Every time I see a CMO that doesn't market themselves, they fail. — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk)...
Dear SaaStr: What Were Your Toughest Times Before Breaking Out?
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...
The Double-Stretch VP Rarely Works Out
"Too many top sales reps want to be a VP. But management isn't for them. It's such a different skill set in sales." @lennysan + me pic.twitter.com/24qbcjbh9k — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) July 10, 2024 Over the past...
What Really Works When Hiring VPs, and How M&A Really Works, with HubSpot Co-Founder and Chair Brian Halligan + Jason Lemkin
HubSpot Chair and co-founder Brian Halligan and SaaStr CEO Jason Lemkin share their advice on what actually works when hiring your SaaS executive team.
HubSpot Co-Founder and Chairman Brian Halligan on AI and SaaS, Board Meetings, and The Incumbent Advantage
SaaStr CEO and Founder Jason Lemkin recently sat down with HubSpot Chairman and co-founder Brian Halligan, who shared valuable insights on the current state of SaaS, evolving board meeting formats, and how AI is reshaping the industry.
Dear SaaStr: Is it Wisest to Approach One Investor at a Time?
Dear SaaStr: Is it Wisest to Approach One Investor at a Time? No. First, it takes too long. If a VC doesn’t know you, and you aren’t a “super hot” start-up, even if you do get a term sheet — it may take months. Yes, term sheets get done in one day. I haven’t done...
Change Management for New Leaders: 4 Practical Tips from Front CEO Dan O’Connell
Dan O’Connell stepped into the CEO role at Front and also previously took over from the founder as CEO at TalkIQ (pre-revenue). Dan shared four practical tips for leaders stepping into new roles – whether as a CEO, executive, or first-time manager. Here’s what he learned about driving effective change while preserving company culture.
Dear SaaStr: What Was Your First Step When You Decided to Do a Startup?
Dear SaaStr: What Was Your First Step When You Decided to Do a Startup? For me, both times, it was to find my co-founder. In my first start-up, arguably I invented the idea of the company, but my co-founder invented the technology. It was really all her. Step 1 was...
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,...
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