9 Signs a Startup Isn’t Going to Make It with SaaStr CEO Jason Lemkin
In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it.
6 Key Signs a VP of Sales Can’t Scale Beyond $5m-$10m ARR
The best VPs can recruit in ways I barely understand You need someone for a key role? They somehow have 2-3 strong candidates in a week or two This is so, so hard But the very best VPs make it somehow look almost effortless It's also the only way to scale —...
What to Do If Your Business Decelerates
A top B2B VC said to me back in the day: “Once a B2B business decelerates, it becomes almost hopeless. No one will buy you, fund you, or join you.” That quote was true then. It’s only gotten more true in 2026. The good thing about B2B is the revenue...
The Pros and Cons of Working Directly for the CEO
Pros of working directly for CEO: – Turbocharges learnings– Accelerated decisions + impact– Lifetime relationship– More rewarding Cons of working directly for CEO: – Feedback can be too direct– Appreciations only for results–...
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started?
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes – 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or...
The Real, Simple Reason CEOs and B2B Execs Get Fired
Dear SaaStr: What are some common reasons that CEOs and other top executives are fired? Ironically, it is rarely for missing the plan — at least at start-ups. Rather, execs and CEOs are fired for (x) hiding that they are missing their plan, and (y) blaming others. The...
Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS?
Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS? To win in Vertical SaaS: – Can you charge at least $10k a year?– Can you add enough value to hit 110%+ NRR?– Can you get to 60% market share? If so, in many markets,...
A Few VP of Sales / CRO Personas to Stay Far Away From
We’ve talked a ton about How to Hire a Great VP of Sales on SaaStr, but I wanted to highlight a few VP of Sales / CRO “personas” that I rarely, if ever, see work out. Because again and again, many of you will hire this VP of Sales / CRO. So many...
If Times Are Tough — Don’t Hide. Be Present.
What I see CEOs at struggling start-ups do: – Go dark– Hide– Lash out– Tweet about lots of things non-work– Invest time on tiny expenses– Argue internally What should do: – Be Present– Be Honest– Be the Rock–...
Dear SaaStr: What Qualities Make a CEO The Best In Their Industry?
Dear SaaStr: What Qualities Make a CEO The Best In Their Industry? I’ve invested in 5 start-ups that had a $1,000,000,000+ cash exit or IPO. The CEOs were all quite different. Some extroverted, some introverted. Some wicked smart, some merely very smart. Some direct,...
7 Of The Top Things Founders Get Wrong When They Start a B2B Company
Dear SaaStr: What do startup founders typically get wrong when starting a business? My list: Not committing to 24 months upfront to getting to Real Revenues and a Minimum Sellable Product. We’ve written about this before, but I see it again and again and again. It...
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk?
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk? It if’s that bad — it’s just not going to work. The issue isn’t so much that he’s a complete jerk. Maybe he is, maybe he isn’t, or most likely, it’s somewhere in the...
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...
Dear SaaStr: My Investor Wants Weekly Meetings. Is This Too Much Time?
Dear SaaStr: I am a startup founder that writes extensive monthly report to investors. We are also doing weekly meetings, are they asking for too much of my time? Yes. Some rough rules: For every 1% of a company an investor owns, an investor should get one meeting a...
CEO & Founder
Related Posts
