Aug 21, 2023 · 19m · saastr
The Top 10 Worst Pieces of SaaS Advice with SaaStr Founder Jason Lemkin
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr presentation, founder Jason Lemkin breaks down the top ten worst pieces of SaaS advice, guiding founders away from counterproductive startup tropes and toward operational realities. He delivers actionable guidance on executive recruitment, enterprise go-to-market execution, fundraising transparency, and sustainable market expansion.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 99.9% of the talking time here. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 0:57 Monologue format baseline
This is a solo monologue episode with no guest disagreement or combativeness.
Hardest push from Jason ▶ 0:57 Monologue format baselineNo host pushback occurs because there is no guest to challenge or press.
Biggest teaching moment ▶ 0:57 Monologue format baselineNo schooling occurs as the episode consists solely of Jason Lemkin presenting his own perspective.
Jason holds their own ▶ 0:57 Monologue format baselineScores are zeroed out across host-side interaction scales due to the solo monologue nature of the episode.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Worst Advice #1: Playing Mind Games with Venture Capitalists | 0 | 0 | 0 | 0 | This is a solo monologue segment where Jason Lemkin discusses why founders should not play mind games with VCs or give VPs of sales endless time. With no active guest dialogue, all interaction scores are zero. | |
| Worst Advice #3: Believing You Can't Afford Top Executive Talent | 0 | 0 | 0 | 0 | Jason delivers a solo breakdown on executive compensation ROI and why freemium/PLG is not an automatic fix for a broken go-to-market strategy. Minor diarization artifacts do not constitute guest participation. | |
| Worst Advice #5: Settling for Junior Hires Instead of Real Leaders | 0 | 0 | 0 | 0 | Jason continues his solo presentation, warning against hiring junior leaders and dismissing competitors. Because this is a monologue, interactive metrics are scored at zero. | |
| Worst Advice #7: Refusing to Participate in Enterprise RFPs | 0 | 0 | 0 | 0 | Jason provides solo insights on enterprise RFPs, compliance requirements, and diagnosing sales versus marketing problems. There is no conversational counterparty or debate. | |
| Worst Advice #9: Making Excuses About Total Addressable Market Size | 0 | 0 | 0 | 0 | Jason delivers monologue analysis on TAM expansion excuses and the necessity of hiring senior product and engineering leaders as companies scale past $10M ARR. | |
| Conclusion: Navigating SaaS Advice and Building for Scale | 0 | 0 | 0 | 0 | A brief solo outro summarizing general takeaways for SaaS founders navigating advice. No interactive host-guest dynamics occur. |
Statements from this episode (16)
Hyper-Successful Founders Inadvertently Give Bad Startup Advice
“And also you sometimes hear bad advice from the hyper successful. Sometimes the folks that are so successful so quickly also can sort of give you wrong advice inadvertently if you're doing pretty darn good, but not great.”
Asking VCs For Advice When You Want Money Is Terrible Advice
“Ask VCs for advice when you want money. Ask for money when you want advice. This is terrible advice.”
A VP Of Sales Showing No Progress In One Cycle Never Improves
“If in a sales cycle, things are not improving on several core metrics and sales, they never will.”
Past $2M ARR, Startups Can Afford Any Executive If They Are Accretive
“After even a couple million in ARR, you can afford any higher if they're accretive.”
A Truly Great B2B SaaS VP Is Always Value Accretive
“I have never in SAS in B to B with, The high margins we have, with the recurring revenue we have, with the upsell opportunities that we generally have. I have never seen a great VP of any role, sales, marketing, customer sales, eng or product, not be a creativ…”
Adding Freemium Tiers Accelerated Growth For Atlassian, HubSpot, And MailChimp
“And in fact, we are seeing more and more companies add freemium additions at lastly and adding free HubSpot, adding free MailChimp, adding free as Three mature examples actually allowed their business to accelerate.”
PLG Leaders Like Asana Do Not Have Lower Sales And Marketing Costs
“If you look at the PLG leaders in SAS and cloud, they're wonderful companies. But the Asana's and the others that they're their cost of sales to marketing isn't lower than the folks that are purely sales led.”
Hiring A Junior Person As Your First Product Hire Never Works
“The junior product person is your first product hire. Never works.”
Junior Marketers Never Generate Real MQLs Or Leads
“The junior marketer might work a tiny bit. Maybe you get some tweets and in some instances, but you never get MQLs and SQLs and leads and the whole thing.”
A 100% Win Rate Means You Are Failing At Marketing And Outbound
“When I hear that we win every deal, I just know it means you're not doing any marketing. You're not doing any marketing and you're likely not doing any outbound in sales either.”
Default Market Leaders Win Enterprise RFPs 80% To 90% Of The Time
“Generally speaking, not always, but generally speaking, when an enterprise vendor goes to the trouble to put together a massive RFP, one, they do it because they're required to, but two, by the time they get there, by the time they spent all the time to issue …”
A Truly Great Sales Rep Can Close 10x What Average Reps Close
“A great sales team can close two X what a mediocre sales team can sometimes more and a truly great rep can often close nine to time, 10 times what an average rep can.”
If Good Inbound Leads Result In Zero Closes, It Is Not Sales
“If nothing, if you have leads and nothing's closing nothing, it's not the sales team because Those leads are good. They're coming in. They found something they like. At least some of them should be closing.”
Most Public SaaS Companies Go Multi-Product Before Reaching 10,000 Customers
“If you look across all the public SaaS companies, most of them get multi-product well before they have 10,000 customers in any market.”