We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.
We discuss:
1. How AI is fundamentally changing the sales function
2. Why most SDRs and BDRs will be “extinct” within a year
3. What Jason is observing across his portfolio about AI adoption in GTM
4. How to become “hyper-employable” in the age of AI
5. The specific AI tools and tactics he’s using that have been working best
6. Practical frameworks for integrating AI into your sales motion without losing what works
7. Jason’s 2026 predictions on where SaaS and GTM are heading next
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Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents
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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation
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Where to find Jason Lemkin:
• X: https://x.com/jasonlk
• LinkedIn: https://www.linkedin.com/in/jasonmlemkin
• Website: https://www.saastr.com
• Substack: https://substack.com/@cloud
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Jason Lemkin
(04:36) What SaaStr does
(07:13) AI’s impact on sales teams
(10:11) How SaaStr's AI agents work and their performance
(14:18) How go-to-market is changing in the AI era
(19:19) The future of SDRs, BDRs, and AEs in sales
(22:03) Why leadership roles are safe
(23:43) How to be in the 20% who thrive in the AI sales future
(28:40) Why you shouldn't build your own AI tools
(30:10) Specific AI agents and their applications
(36:40) Challenges and learnings in AI deployment
(42:11) Making AI-generated emails good (not just acceptable)
(47:31) When humans still beat AI in sales
(52:39) An overview of SaaStr's org
(53:50) The role of human oversight in AI operations
(58:37) Advice for salespeople and founders in the AI era
(01:05:40) Forward-deployed engineers
(01:08:08) What's changing and what's staying the same in sales
(01:16:21) Why AI is creating more work, not less
(01:19:32) Why Jason says these are magical times
(01:25:25) The "incognito mode test" for finding AI opportunities
(01:27:19) The impact of AI on jobs
(01:30:18) Lightning round and final thoughts
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Referenced:
• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org
• SaaStr Annual: https://www.saastrannual.com
• Delphi: https://www.delphi.ai/saastr/talk
• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/
• Vercel: https://vercel.com
• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Replit: https://replit.com
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• ElevenLabs: https://elevenlabs.io
• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack
• Bolt: https://bolt.new
• Lovable: https://lovable.dev
• Harvey: https://www.harvey.ai
• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence
• UiPath: https://www.uipath.com
• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser
• Agentforce: https://www.salesforce.com/form/agentforce
• SaaStr’s AI Agent Playbook: https://saastr.ai/agents
• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan
• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan
• Sierra: https://sierra.ai
• Fin: https://fin.ai
• Deccan: https://www.deccan.ai
• Artisan: https://www.artisan.co
• Qualified: https://www.qualified.com
• Claude: https://claude.ai
• HubSpot: https://www.hubspot.com
• Gamma: https://gamma.app
• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b
• Brex: https://www.brex.com
• Outreach: https://www.outreach.io
• Gong: https://www.gong.io
• Salesloft: https://www.salesloft.com
• Mixmax: https://www.mixmax.com
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr
• Clay: https://www.clay.com
• Owner: https://www.owner.com
• Momentum: https://www.momentum.io
• Attention: https://www.attention.com
• Granola: https://www.granola.ai
• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff
• Palantir: https://www.palantir.com
• Databricks: https://www.databricks.com
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan
• Rippling: https://www.rippling.com
• Cursor: https://cursor.com
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna
• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza
• Sora: https://openai.com/sora
• Reve: https://app.reve.com
• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/
• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
How the Smartest Founders Are Quietly Winning with AI
Episode 713: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Jason Lemkin ( https://x.com/jasonlk ) about cloning yourself with AI and how ChatGPT will be the end of incumbent apps.
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Show Notes:
(0:00) AI body doubles Users tell AI things they won't tell humans
(15:15) The incumbents are dying
(27:25) Inside the office of OpenAI
(34:12) How to be an AI billionaire
(44:40) The story of Saastr
(55:49) Being a relentless recruiter
(58:52) Seeing through the fog of war
(1:07:53) The future of work for gen alpha
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Links:
• Want Sam's playbook to turn ChatGPT into your executive coach? Get it here: https://clickhubspot.com/ejv
• Saastr - https://www.saastr.com/
• Delphi - https://www.delphi.ai/
• Windsurf - https://windsurf.com
• Coursiv - https://coursiv.io/
• Lovable - https://lovable.dev/
• Higsfield - http://higsfield.ai/
—
Check Out Shaan's Stuff:
• Shaan's weekly email - https://www.shaanpuri.com
• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.
• Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies!
Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC
20VC: Why Seed is for Suckers | a16z's $20BN Fund & Founders Fund's $4.6BN: What Makes Them So Good | Why Josh Kushner Is the Master of Venture Capital Strategy | Why Extended Private Markets Screw US Citizens with Jason Lemkin and Rory O'Driscoll
Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more.
Rory O'Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.
In Today's Episode We Discuss:
04:23 What is Wrong with Billionaires on Twitter: Are They Depressed?
08:49 Why Does product Market Fit Mean Less Than Ever
11:50 Why is Venture Capital More Risky Than Ever and No One is Discussing It
16:17 Will Private Equity Save a Generation of SaaS Companies and VCs
23:53 a16z's $20BN Fund: Seriously?
31:29 Why Josh Kushner and Thrive Capital are Masters of the World
38:21 Why is Seed Investing for Suckers
45:49 Why Are $50 Million Seed Funds Useless
46:21 Founders Fund Raises $4.6BN: Analysis
52:00 How WIll LPs Change Their Approach to Venture in the Next Five Years
59:53 When Will IPOs Comeback?
01:09:15 Why Does it Not Make Sense for the Best Companies to IPO
01:09:51 Lost Ethics and Morals in Founder Secondaries and Term Sheets
01:22:58 Quickfire: OpenAI, Cursor, Deel vs Rippling
23andMe BANKRUPT, Saylor Still Buying Bitcoin, + Founder Interviews | E2102
Today’s show: In this episode, Alex and Lon kick things off with the latest tech news — including 23andMe’s dramatic collapse, MicroStrategy’s half-million Bitcoin haul, and whether we’re finally seeing a rebound in startup M&A. Then they sit down with three standout founders building the future across AI chips, data privacy, and healthcare. First up, Etched CEO Gavin Uberti explains why they’re betting big on transformer-specific ASICs. Then, Skyflow co-founder Anshu Sharma breaks down how they’re helping enterprises use LLMs without leaking private data. Finally, MedServe’s team walks us through how they’re securing medications in outpatient clinics and staying on the right side of the DEA.
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Timestamps:
(0:00) Alex kicks off the show
(1:15) 23andMe bankruptcy and SPACs impact
(5:23) MicroStrategy's Bitcoin strategy
(8:58) Increase in M&A activity and market trends
(10:06) Northwest Registered Agent - Get a 60% discount on your next LLC at https://www.northwestregisteredagent.com/twist
(13:37) Browser use, agentic AI, and VC market insights
(19:28) Financial responsibility in startups
(20:28) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST
(21:56) Interview with Gavin Uberti of Etched
(30:32) Fidelity Private Shares℠ - Visit https://www.fidelityprivateshares.com ! Mention our podcast and receive 20% off your first-year paid subscription.
(32:12) Economic and technical aspects of chip efficiency
(39:53) Etched's market demand, manufacturing, and AI scaling
(43:05) Founder insights and hardware startup potential
(45:43) Introduction to Skyflow and Anshu Sharma
(50:19) Skyflow's growth and customer acquisition strategies
(1:03:09) ServiceNow's new product and Skyflow's bullish outlook
(1:06:33) M&A interest and AI stack value creation
(1:12:06) Skyflow's funding and cybersecurity customer trust
(1:13:12) Introduction to MedServe and Milwaukee's startup ecosystem
(1:16:30) MedServ's solution to drug dispensing and diversion
(1:23:05) Economic challenges and solutions for smaller facilities
(1:26:50) MedServe cabinet features and use case demonstration
(1:29:51) Cybersecurity and physical security of MedServe systems
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Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Follow Etched:
Website: https://www.etched.com/
X: https://x.com/Etched
LinkedIn: https://www.linkedin.com/company/etched-ai/
*
Follow MedServe:
Website: https://medserverx.com/
X: https://x.com/MedServeRX
LinkedIn: https://www.linkedin.com/company/medserverx/
*
Follow Skyflow:
Website: https://www.skyflow.com/
X: https://x.com/SkyflowAPI
LinkedIn: https://www.linkedin.com/company/skyflow/
*
Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm
*
Follow Lon:
X: https://x.com/Lons
*
Thank you to our partners:
(10:06) Northwest Registered Agent - Get a 60% discount on your next LLC at https://www.northwestregisteredagent.com/twist
(20:28) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST
(30:32) Fidelity Private Shares℠ - Visit https://www.fidelityprivateshares.com Mention our podcast and receive 20% off your first-year paid subscription.
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
This Week in SaaS: Should Wiz Have Accepted Google's $23BN Acquisition Offer, Crowdstrike: WTF Happens From Here: The Bull and the Bear Case & $1BN into Legal Tech in a Day with Clio and Harvey with Jason Lemkin
Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com.
In Our Second Episode of This Week in SaaS:
1. Wiz Rejects Google's $23BN Acquisition Offer:
How does Jason analyse the price of the offer? $23BN for a $500M ARR business growing 120% YoY?
What is the reasoning for Google in pursuing the acquisition?
If Wiz had of proceeded in the process, what are the chances it would have made it through regulators?
Why did Wiz walk away from the offer? If Jason were on the board, what would he have done?
Is there a correlation between the downfall of Crowdstrike and Wiz turning down the offer?
What does this mean for the M&A market moving forward?
Will there be a secondary round now in place for Wiz at $23BN?
2. Crowdstrike: WTF Happens from Here:
Did Crowdstrike manage the crisis in the right way? What would Jason have done differently?
What is the bull case for Crowdstrike moving forward from this point?
What are the bear case for the company? Could this snowball and be the end?
What will this do to company requirements on having single point of failure solutions?
Where will the market cap of Crowdstrike be at the end of 2024?
3. LegalTech: Show Me the Money: $1BN in a Single Day:
Clio announced a $900M round at a $3BN valuation. How does Jason analyse this?
What does Jason make of Harvey's $100M raise at a $1.5BN valuation?
Why does Jason think 2025 will be the year for AI parity? Why will we see the majority of SaaS features be commoditised in 2025?
What is the single biggest regret that Jason has in his investing career?
This Week in SaaS: PluralSight Goes to Zero, Salesforce and Mongo Hit Hard, The Next IPO Candidates and How Do We Solve the Problem of Liquidity in Venture Capital
Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com.
In Our First Ever Episode of This Week in SaaS
1. PluralSight Goes to Zero:
WTF happened to PluralSight? How did it go from $3.5BN to $0?
Will this have a wider impact on the willingness of PE to buy tech companies?
Who are the next contenders to go from hero to zero? Zendesk? Anaplan?
Will this generation of PE funds be let off by their LPs for a poor vintage?
2. Salesforce's Worst Stock Market Drop Since 2004 + Mongo Takes a 23% Hit:
Why did Salesforce lose $50BN of market cap in a single day?
Is the same true for MongoDB taking a 23% hit in one day?
What does it mean when the new normal is these once hyper-growth companies now growing only 6% per annum?
3. The Settlers into Slow Growth:
Why does Jason believe that Dropbox and Box have both settled into a world of slow growth?
What happens to Twilio from here in a world post Jeff Lawson?
What happens to Retool from this point on?
Would Jason be a buyer of Notion at $10BN?
4. Venture Capital is Broken:
Why does Jason believe that we need to see a relation of public multiples for the math in venture capital to work again?
Why does Jason believe that the way we mark portfolios with TVPI leads to corrupt and bad behaviour?
How does Jason think we will solve the problem of liquidity with IPOs being shut, M&A being out of the window and now PE being a doubt as the source of buyers?
20VC: Why Seed is Systemically Broken | Why Pricing is Worse Than Ever and There is More Funding Than Ever | Benchmarks for Churn, Retention and Growth Rates - Good vs Great | Why Last Vintage for Private Equity Will Suck with Jason Lemkin
Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com.
In Today's Episode with Jason Lemkin We Discuss:
1. Growth Rates and Churn Rates: Average/Good/Great:
What is a growth rate that would excite Jason in a SaaS company? What is average?
What levels of churn would worry Jason to see? What would excite him to see?
What does Jason never tolerate when it comes to either growth rate or retention?
2. What Founder Combination Always Wins:
Why does Jason believe you cannot lose money on a CEO salesperson and a technical CTO founding partnership?
Why does Jason always meet the CTO for a second meeting in the diligence process? What questions does he ask? What do the best CTOs do or say?
Why does Jason always want to sell his shares when the founders want to sell?
Why does Jason believe that a company is never the same when the founders leave?
3. WTF is Happening in the World of VC:
Why does Jason believe that pricing is worse than it has ever been in venture?
Why does Jason believe that traditional seed VC is systemically broken?
Why are companies getting stuffed with more cash than ever before?
What does Jason know now about dilution that he wishes he had known when he started?
Why does Jason believe that you should always recycle everything?
4. WTF is Happening in PE and Later Stage Markets:
What happens to all the overpriced acquisitions like Zendesk and Salesloft where private equity way overpaid for them, they have no growth and no product innovation?
What happens to the generation of public companies like Box, Dropbox and Twilio, all with low growth and little product innovation in the single-digit market caps?
Why does Jason believe that Klaviyo is the most undervalued public company today?
What does Jason believe will happen to Anaplan with Pigment eating their lunch?
How I Reverse Engineered A $100 Million Exit - Jason Lemkin
Episode 571: Sam Parr (https://twitter.com/theSamParr) talks to Jason Lemkin (https://twitter.com/jasonlk ) talk about the 7 rules of building a $100M business.
Want to see Sam and Shaan’s smiling faces? Head to the MFM YouTube Channel and subscribe - http://tinyurl.com/5n7ftsy5
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Show Notes:
(0:00) Jason Lemkin’s first million
(4:19) The rules of getting to a 9-figure exit
(5:32) Rule 1: New minimum is $400K per employee
(7:58) Rule 2: Go multi-product
(9:40) Rule 3: Your second product must be bigger than your first product
(11:05) Cheat code: Double your prices
(13:48) Rule 4: 30% of your revenue is international
(15:43) Rule 5: Localize your product
(19:05) Cheat code: Remove friction
(22:42) Rule 6: 100% net revenue retention
(29:01) Business models that won’t get you there
(33:38) $100M conferences
(39:35) Rule 7: Don’t raise double digit millions
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Links:
• Saastr - https://www.saastr.com/
• HLTH - https://www.hlth.com/
—
Check Out Sam's Stuff:
• Hampton - https://www.joinhampton.com/
• Ideation Bootcamp - https://www.ideationbootcamp.co/
• Copy That - https://copythat.com
• Hampton Wealth Survey - https://joinhampton.com/wealth
—
Check Out Shaan's Stuff:
Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd
My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano
Building a world-class sales org | Jason Lemkin (SaaStr)
Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss:
• How far you should go without a salesperson
• Signs it’s time to hire salespeople
• Why you need to hire two salespeople
• How to compensate your salespeople
• How to interview salespeople
• When to hire a VP of Sales
• How to prevent their flaming out
• How to scale your sales org
• How to improve the relationship between your sales and product teams
• Much more
—
Brought to you by:
• CommandBar—AI-powered user assistance for modern products and impatient users
• Vanta—Automate compliance. Simplify security.
• LinkedIn Ads—Reach professionals and drive results for your business
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Find the full transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-sales-org
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Where to find Jason Lemkin:
• X: https://twitter.com/jasonlk
• LinkedIn: https://www.linkedin.com/in/jasonmlemkin/
• Website: https://www.saastr.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Jason’s background
(06:18) The importance of sales in B2B businesses
(11:23) Signs that you should start hiring salespeople
(14:19) Attributes to look for in early sales reps
(19:08) Hiring a VP of Sales
(26:43) The role of a VP of Sales
(30:06) Interviewing salespeople
(45:16) Determining sales compensation and quota
(53:34) Transitioning from 100% commission to a smaller percentage
(56:58) Indicators of a hard-to-sell product
(59:39) Scaling the sales organization
(01:05:26) Understanding sales roles and titles
(01:10:02) Product involvement in sales, and vice versa
(01:20:32) Thoughts on product teams taking on P&L responsibilities
(01:27:23) One thing founders can do to become better at sales
(01:31:02) The ideal trial length for a free trial sales team
(01:39:50) Closing thoughts
(01:41:43) Lightning round
—
Referenced:
• Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/
• Snowflake: https://www.snowflake.com/en/
• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/
• Salesforce: https://www.salesforce.com/
• HubSpot: https://www.hubspot.com/
• Twilio: https://www.twilio.com/
• Cloudflare: https://www.cloudflare.com/
• GitHub: https://github.com/
• Columbo: https://www.imdb.com/title/tt1466074/
• What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti
• Adobe: https://www.adobe.com/
• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/
• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A
• The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY
• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/
• Pipedrive: https://www.pipedrive.com/
• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/
• Gong: https://www.gong.io/
• Zendesk: https://www.zendesk.com/
• ZoomInfo: https://www.zoominfo.com/
• Apollo: https://www.apollo.io/
• Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/
• SAP: https://www.sap.com/
• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/
• VistaPrint: https://www.vistaprint.com/
• Procore: https://www.procore.com/
• Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/
• Wordpress: https://wordpress.com/
• SaaStr University: https://app.saastruniversity.com/collections/20252
• From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691
• Pavilion: https://www.joinpavilion.com/
• Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw
• The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK
• Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick
• OpusClip app: https://www.opus.pro/
• OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/
• SaaStr conferences: https://www.saastr.com/events/
• Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html
• Zoomtopia: https://zoomtopia.com/
• Money20/20: https://us.money2020.com/
• Shoptalk: https://shoptalk.com/
• Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/
• Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Why one founder thinks the Apple Vision Pro is going to make it
This is our interview show, where we sit down with interesting, knowledgeable folks and dive deep into what they are building, designing, or thinking about.
Today, we have Anshu Sharma back on the podcast. Last time, the Skyflow CEO riffed with us on interest rates and business cycles. This time, we wanted to talk to him about a theory he recently wrote up for TechCrunch: The Innovator’s Dilemma.
Or perhaps, a partial solution to that dilemma. The gist is that instead of using lower-cost products to take on incumbents, you might want to start at the top end of the market. This comes to bear today with the Apple Vision Pro headset, which is very expensive, and is entering a category replete with big investments and occasional returns.
Equity will be back tomorrow with our regular news roundtable, so we’ll chat with you soon!
For episode transcripts and more, head to Equity’s Simplecast website.
Equity drops at 7 a.m. PT every Monday, Wednesday and Friday, so subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. TechCrunch also has a great show on crypto, a show that interviews founders and more!
Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.
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20VC: Predictions for 2024: What Happens to Early Stage VC Funding, Do a Load of Venture Funds Die, What do LPs Do in 2024, Does Figma Kill the M&A Market, Will IPOs Comeback & What Does a Trump Administration do for Startups with Jason Lemkin @ SaaStr
Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments:
2023: A Year in Review:
Breakout company
Best early-stage fund
Best late-stage fund
Most surprising event
Founder of the Year
2024: Predictions: What is to Come:
Does the IPO window open?
Do Stripe, Databricks, and more go public?
What happens to early-stage venture markets?
Does the growth stage come roaring back?
What happens to the M&A market?
How does Trump change the startup ecosystem?
Will a generation of young VCs be washed out the system?
Will a ton of venture firms shut down?
20VC Roundtable: Why Early Stage Founders Should Not be Investing, Why Great Founders Have Low EQ, How the Structure of VC Firms Will Change, Will Founder-Led Funds Compete with Sequoia & Is Investing a Team Sport?
Jack Altman is the Founder and CEO @ Lattice, the #1 people management platform, last valued at $3BN. Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth, Owner.com, Mercury and more.
Auren Hoffman is the Founder and CEO @ Safegraph, the most accurate database of global points of interest, last valued at $550M. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more.
Jason Lemkin is the Founder and CEO @ SaaStr, the world's largest SaaS community. Jason is an investor through his founding of The SaaStr Fund. In the past, Jason has invested in Pipedrive, Algolia, Salesloft, Front, GreenHouse, Owner.com, Gorgias and more.
In Today's Episode on Founder-Led Funds We Discuss:
Why have we seen the rise of "Founder-led Funds"?
Are founder-led funds more empathetic to the founders they invest in?
How do founder-led funds source and pick investments in a way that traditional VC does not?
Will we see founder-led Funds truly compete against the Sequoias of the world?
How does being an operator make you a better investor?
How does investing help you be a better founder and operator?
How do you communicate your investing practice and firm to your company and team?
What are the biggest excitements and concerns LPs have for Founder-led Funds?
Will we see the face of venture changing much more broadly and structurally?
How do founder-led funds manage both time and company conflicts?
20VC Roundtable: Are IPOs Back? Is Growth Dead? What Does it Take to Raise a Growth Round Today? How Do VCs Solve The Liquidity Challenge? Will We See a Massive Resetting of Valuations? AI Hype Growth Rounds?
Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years. Deven has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba, JD.com, Chargebee and Automattic (WordPress) to name a few.
Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies.
Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few.
In Today's Episode We Discuss:
1. The Growth Landscape Overview:
Is growth dead? Are any growth deals getting done?
How has the price changed for growth deals that are getting done?
Which type of growth companies will vs will not be able to raise?
What happens to all of the growth companies with $300-$500M in cash but little revenue?
2. The Great Reset: Valuations Need to Change:
Why should companies be actively resetting their valuations? What are the benefits?
What will happen between VCs and LPs when there is no incentive for VCs to reset their portfolio valuations when they need to go out and raise from those same LPs?
Structure is often part of these valuation resets, is structure to rounds always bad? When is it good? What type of structure is acceptable vs unacceptable?
3. Are the Public Markets Creeping Open:
Should we take comfort from ARM, Instacart and Klaviyo and assume the public markets are going to open again? If not, what will cause them to open?
How should we analyze the performance of the IPOs above? Many have been negative, are they right to suggest this is not the response we wanted?
Why does Woody believe, like Instacart taking a 75% discount to their last round, we should have more and more companies go public at discounts to their last private round?
4. Late Stage Growth is Dead and Revenue Multiples:
Why is late-stage growth dead? How long do we think this will last?
How should we assess revenue multiples today? New normal? Same as always? How will revenue multiples look in 12 months from now?
How should we analyse the large late stage growth rounds for hyped AI companies? What happens there?
20VC Roundtable: Is the VC Model Broken? The Biggest Disconnect Ever Between TVPI & DPI, Why Market Size is Dangerous, Why "Go Fast" is Terrible Advice, The Dangers of Raising Large Rounds at High Prices & Why Next Year Will See the Biggest Hiring Spree i
Eric Paley is the Managing Partner at Founder Collective, one of the world's most successful seed funds with investments in the likes of Uber, The Trade Desk, Coupang and Airtable.
Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more.
Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds with a portfolio including Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few.
In Today's Episode on Is the Venture Model Broken? :
Is the classic seed model dead? Can seed funds play in a world of $25M valuations?
Why is having a firm grasp of the present the best thing an early-stage investor can have?
Why does Mike Maples believe no company with true product-market-fit has ever failed?
Why does Eric Paley believe "go faster" is the worst startup advice?
Why does Mike Maples believe there is a direct relationship between price and risk?
Why does Mike Maples believe that outliers by their very nature are lower priced?
Why does Eric Paley not focus on ownership? Why can it be dangerous?
What are the biggest risks for founders raising at valuations that are too high?
Why does Eric Paley believe we will have the biggest chasm between TVPI and DPI in the prior vintage of venture capital returns?
Why does Eric believe the majority of SPACs were BS and great companies can always go public?
Why does Jason believe that if multiples do not reflate, the venture model is broken?
Why does Jason believe we will see the biggest hiring spree in tech next year?
How has illiquidity allowed Eric Paley to make some of the best investment decisions?
What is Mike Maples biggest lesson from selling Twitter stock early at $1BN?
20VC: NEW FORMAT: Mega Funds Will Come Back, Why Markups Have Corrupted VC, Why RIFs Should Always Be An Embarrassment To SaaS Founders and Why Pitching is BS and Fake with Jason Lemkin and Rick Zullo
Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.
Rick Zullo is the Co-Founder and General Partner at Equal Ventures. Prior to co-founding Equal Ventures, Rick was an investor at Lightbank, Prior to Lightbank, Rick worked with investment firms Foundation Capital, Bowery Capital, and Lightview Capital.
In Today's Episode We Discuss:
1. Why Venture Capital Needs It's Jerry Maguire Moment:
Why does Rick believe that VC needs it's "Jerry Maguire" moment?
What needs to change? What needs to stay the same?
Why does Jason believe we will see even more mega funds in 2024 and 2025?
2. Unicorns are So 2019:
Why does Jason believe that "unicorn investing is mostly dead for bigger funds and none of them are looking for a $1BN outcome anymore?"
Why does Rick believe that multi-stage fund investing at seed simply does not make sense?
What does Rick believe many founders need to know when they take multi-stage money at seed?
Of the over 1,000 unicorns created over the last few years, how many of them do Rick and Jason feel are actually unicorns today?
3. Efficiency and Growth: We Need it All:
Why does Jason believe, as a founder you should be embarrassed if you ever had a RIF (reduction in force)?
Last year many founders got a pass on growth as they were more efficient. Is that pass over? Do they need to get back to growth?
What is the single biggest reason that companies do not scale from seed to Series A?
What happens to the many companies with years of runway but no product-market-fit?
Are we entering a new age of efficient company building or will we go back to high burn environments and excessive spending?
4. Entering the World of LPs:
If Jason and Rick were to advise LPs today on how much to discount the value of their venture books, what advice would they give?
How have markups completely corrupted the venture ecosystem?
How does LPs being incentivized by paper-marks make the industry even more screwed?
What are the single biggest misalignments between GP and LP?
20VC Roundtable: NEW FORMAT: Why the Seed Investing Model is Broken, How to Make Money at Seed Moving Forward; Who Wins and Who Loses, Why Venture Value Add Platforms are BS and Failed and Why There Will be an IPO per Week in H2 2024
Sam Lessin is a Co-Founder and Partner @ Slow Ventures with a portfolio including the likes of Airtable, Robinhood, Slack, Solana, PillPack and many more unicorn companies. Prior to Slow, Sam was a VP Product at Facebook having sold his company to Meta.
Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. As for Frank, prior to QED, Frank was one of the earliest analysts hired into Capital One and spent almost 13 years there helping build many of the company's business units and operational areas.
Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.
In Today's Discussion on Why Seed is Broken We Discuss:
1. The Seed Model Was Broken and What Comes Now:
Why does Sam Lessin believe the model for seed of a "factory line" was broken?
What does he believe will replace it?
Why does Jason Lemkin argue that this might not be the case for SaaS and enterprise?
2. Round Construction: YC, Multi-Stage Funds and Party Rounds:
Why does Sam Lessin believe we have seen the end of party rounds? Why does Jason Lemkin disagree and we will see more than ever?
Why does Sam Lessin believe the factory model of YC churning out companies is over? Where does Jason Lemkin believe the value lies in the YC model?
Will the multi-stage funds remain in seed? How has their entrance and deployment changed the seed market?
3. VC Value Add at Seed: Is it BS?
Why does Jason believe all talent arms in venture firms have failed?
Why does Sam believe that no VCs provide value?
Do the best founders really need help? Why do Jason and Sam disagree?
4. What Happens Now:
Why does Jason believe that every manager can write off their fund from 2021?
Who will be the winners in seed in the next 10 years?
Why does Sam believe if you want to bet on AI, just bet on Meta or Microsoft?
What will happen to the many companies with no PMF but 10 years of runway?
20VC: The Memo: The State of the VC Market: Why Seed Funds Can't Invest in "Hot Startups" Anymore, Why Series A & B is Terrible, Why the IPO Market Will Explode in 2024 & Why VC DD is BS & Every VC Has More Fraud in their Portfolio with Jason Lemkin
Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.
In Today's Episode with Jason Lemkin We Discuss:
1. WTF is Happening At Seed Right Now:
Why does Jason believe seed is more active than ever?
Is the pricing of seed rounds impacted since the downturn?
Why does Jason believe it is not only not the end of party rounds but just the beginning of them?
Why does Jason believe you cannot fail if you have $1M in ARR and an amazing founder?
Why does Jason believe that seed investors cannot participate in "hot seed rounds" anymore?
2. Is Series A a Dead Zone:
How does Jason analyze the Series A and B environment today?
What has changed in what investors expect and want to see in potential Series A and B investments?
What happens to the many companies who raised pre-emptive Series As and have 10 years of runway but no product-market fit?
Why does Jason believe founders should offer to give the money back when it is not working?
What happens to the Series A and B market in the next 18 months? When does it come back?
3. Growth: People are Too Negative!
Why does Jason believe that growth is more active than many are giving credit for?
What are the ARR benchmarks required to get a good growth round term sheet today?
Why does Jason believe that VC DD is a load of BS?
Why does Jason believe that every VC has fraud in their portfolio? Will they come out?
4. Ring That Bell: IPOs and M&A:
Why does Jason believe 2024 will be an amazing year for IPOs?
Why does much of the IPO market rely on Stripe and Databricks?
What is needed for an amazing 2024 IPO market?
How does Jason evaluate the M&A market in 2024? Will regulation get in the way?
5. Jason Lemkin: AMA:
Why does Jason Lemkin believe this generation of workers will never work hard again?
What is the only way for seed funds to make money investing in serial entrepreneurs?
What does Jason know now that he wishes he had known when he started investing?
Competitive Differentiation: 10 Years Then 400% Growth
Anshu Sharma spent 10 years thinking about one problem before writing a line of code. When he finally launched Skyflow with a SaaS go-to-market strategy built on competitive differentiation through deep expertise, the first customer call ended in a sale.
Learn how Skyflow achieved competitive differentiation by creating an entirely new product category - a privacy API for sensitive data. Anshu built the product for 12 months without a single customer conversation, defying conventional startup wisdom. The result: 400% year-over-year growth, $70M raised, and 100+ customers through thought leadership content that educated the market from first principles.
This is a masterclass in competitive differentiation for founders building category-creating products where no market exists yet. Anshu also shares how he saved a major customer who tried to cancel after a leadership change.
Key Lessons
🎯 Deep expertise replaces customer discovery for competitive differentiation: Anshu studied data privacy for 10 years at Salesforce and Oracle, making interviews unnecessary because he knew the problem better than buyers.
🏢 Category creation requires a different SaaS go-to-market playbook: New infrastructure categories need enough product built for a CTO to see why the architecture is fundamentally different.
📉 Customer cancellations become growth opportunities: When Skyflow's largest customer tried to cancel after a leadership change, Anshu listened to the new CTO's priorities and turned a critic into a champion.
💰 Thought leadership drove competitive differentiation from 10 to 100 customers: Blog posts explaining from first principles why a data privacy vault was needed generated inbound leads consistently.
🚀 Seed investors fund asymmetric bets on new categories: Most VCs rejected Skyflow, but one saw a company that could become worth $100B if it worked, leading to a $6M seed round.
Chapters
Introduction
Anshu's favorite quote from Marc Benioff
What Skyflow does and how it works
Skyflow's ideal customer profile
Revenue, growth, and team size
How tokenization and data vaults work
Origin story - 10 years of seeing the privacy problem
What triggered the decision to finally start Skyflow
Building the MVP without talking to customers
How long the MVP took to build
Self-funding vs raising - first 6 months
Why category-creating companies cannot pivot
MongoDB and the category creation pattern
Getting the first 10 customers
Why Anshu sets context before showing demos
Narrowing down the ICP for a horizontal product
Getting from 10 to 100 customers with thought leadership content
Story of a customer trying to cancel
Lightning round
Resources
Full show notes: https://saasclub.io/363
Join 5,000+ SaaS founders: https://saasclub.io/email
20VC: WTF is Going On in VC? Are VCs Still Investing? How Has What VCs Want in Investments Changed? Are LPs Investing in New Funds? Why VCs That Invest in Public Markets Are Losers? Dec 2023; Will It Be Better Or Worse with Jason Lemkin
The question is: "are VCs still investing?". Today we are joined by Jason Lemkin; one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World's Largest Community for Business Software." Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M.
In Today's Episode on "Are VCs' Still Investing" We Discuss:
1. What Does it Take To Get Funded Today:
Early-Stage:
How has what VCs want in early-stage investments changed in this new environment?
Should startups prioritize growth? Profitability? Capital efficiency?
How long a runway is sufficient enough for founders to feel comfortable?
Why does Jason believe most founders are still deluded that they are fundable?
Growth Stage Companies:
Is the growth stage totally dead?
What will we see happen to all the companies that raised $50M+ at large valuations that have very little revenue?
Why does Jason believe that any operator who joined a $BN company in the past few years will not make any money on their equity? What should they do now?
Will we start to see down rounds and structured rounds at the growth stage? If so, when?
Public Markets:
Why does Jason believe this is a time unlike any he has seen before?
Are we in full recession now in Jason's mind? In Dec 2023, will this be better or worse?
Which are the most under-priced assets in the public markets today?
Why does Jason believe VCs investing in public markets are losers?
2. Micro Funds Will Be Decimated and LP Behaviour in 2023
Why does Jason believe that micro-funds in 2023 will be decimated and unable to raise new funds?
How will the majority of LPs approach new fund investments?
How will LPs approach re-investing in their existing managers? How has what they need to see changed?
3. Marketing and Sales: We Need To Change Budgets and Targets
How should CEOS be changing their marketing budgets in 2023?
What are the single biggest mistakes CEOs are making in this downturn with regard to their marketing budget?
How do sales targets need to be amended in the face of changing buying patterns?
How do the best sales and marketing leaders respond to these changing budgets and targets? How do the worst respond?
20VC: Jason Lemkin on Why Founders Do Not Care About Their VCs Anymore, Why Zoom Made Us All Worse Investors, Why 80-90% IRR Should Have Been Warning Signs and the Algolia Journey From Seed to $2.25BN Valuation
Jason Lemkin is one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World's Largest Community for Business Software." Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M.
In Today's Episode with Jason Lemkin On Algolia We Discuss:
1.) Meeting the Unicorn: Algolia:
How did Jason first come to meet Nicolas (Founder) and Algolia?
What specific elements of cold emails make the best attract Jason's attention? What do they have in them? What are the most common mistakes people make with cold emails?
What is the single biggest mistake Jason made when making the deal with Algolia? How did Jason lead their seed round when their round was "oversubscribed"?
2.) Competition and TAM: The Reasons To Say No:
Competing with Free: How did Jason analyze the competitive landscape Algolia was facing? How did he gain comfort that they could compete and win against free and open-source?
TAM Analysis: The TAM at the time for Algolia was $2M. How did Jason analyze the TAM at the time? How did he get comfortable with such a small TAM?
What are the single biggest mistakes investors make when analyzing competition today? What are the biggest mistakes founders make when presenting the competitive landscape?
What are the single biggest mistakes investors make when analyzing TAM today? What are the biggest mistakes founders make when presenting the TAM and how it breaks down?
3.) Investing Lessons Transition from CEO to VC:
Jason has previously said one of his biggest lessons is "bet on what you know when you go from CEO to VC"? What did he mean by this?
How can one keep this operator knowledge and mentality when one is a VC for a long time?
What are the biggest pieces of advice that Jason would give to operators becoming investors?
What are the biggest mistakes that Jason made in his first 3 investments as a VC? How did he change?
4.) Mastering the World of Venture Today:
Why does Jason believe that he has become a worse investor with the rise of "remote investing"?
Why does Jason believe he is a worse investor without having a partner in SaaStr Fund?
Why does Jason believe that even the best founders do not want hard feedback anymore? Should we as VCs still give it to them? What has Jason learned here?
Will we see great LP churn and many LPs leaving the asset class? What will happen to the existing incumbents with massive AUM and reduced performance?
SaaStr 604: SaaStr CRO Confidential Presents How to Fundraise in Late 2022 with SaaStr CEO and Founder, Jason Lemkin. Hosted by Sam Blond, Partner at Founders Fund
Founders Fund Partner and former Brex CRO Sam Blond joins the SaaStr podcast to host this series with SaaS CROs.
But first, to kick off the CRO Confidential series, Sam chats with SaaStr CEO Jason Lemkin about whether tech founders still need to be based in SF, the current correction of the VC market, and what to look for in an investor.
Full video: https://youtu.be/rwHdE318dqA
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
Subscribe for weekly updates: https://www.saastr.com/subscribeform
Twitter: https://twitter.com/saastr
LinkedIn: https://www.linkedin.com/company/2724976
Quora Group: https://www.quora.com/q/cloud
Facebook: https://www.facebook.com/SaaStr/
Instagram: https://www.instagram.com/saastr/
Our North American Event: https://bit.ly/2OXeAYh
Our European Event: https://bit.ly/2OZTad8
SaaStr 603: SaaStr CRO Confidential Presents the Ultimate Guide to Sales Compensation, Quotas and Recruiting with SaaStr CEO and Founder, Jason Lemkin. Hosted by Sam Blond, Partner at Founders Fund
Founders Fund Partner and former Brex CRO Sam Blond joins the SaaStr podcast to host this series with SaaS CROs.
But first, to kick off the CRO Confidential series, Sam chats with SaaStr CEO Jason Lemkin about gross margins, macro impact on 2022 revenue, and sales leadership recruiting.
Video: https://youtu.be/yAyym4uJMcs
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
Subscribe for weekly updates: https://www.saastr.com/subscribeform
Twitter: https://twitter.com/saastr
LinkedIn: https://www.linkedin.com/company/2724976
Quora Group: https://www.quora.com/q/cloud
Facebook: https://www.facebook.com/SaaStr/
Instagram: https://www.instagram.com/saastr/
Our North American Event: https://bit.ly/2OXeAYh
Our European Event: https://bit.ly/2OZTad8
SaaStr 579: Why Event Marketing Matters Even More Than Before & The Future Of Events with SaaStr CEO Jason Lemkin
SaaStr's own Poya Osgouei has a great Uncharted podcast that does a deeper dive with many SaaS execs.
Up this week is our own Jason Lemkin, Founder and CEO of SaaStr.
We're cross-posting this great deep dive episode where they discuss how SaaStr has evolved over the last 10 years, and discuss the importance of focusing on field marketing now that folks are eager to get back together.
SaaS multiple compression, downturn outlook & advice for new VCs with Jason Lemkin of SaaStr | E1461
Jason and Molly chat with Jason Lemkin of SaaStr (01:44). They discuss: advice for new VCs (16:14), the future of SaaS investing (27:37), playing offense as investors (35:50), secondaries and more.
(00:00) Jason and Molly tee up today’s interview show
(01:44) Jason and Molly speak with Jason Lemkin of SaaStr
(14:59) Notion - Get started for free at https://notion.com/thisweekinstartups
(16:14) Jason Lemkin’s advice for new fund managers
(26:16) Microacquire - Sell your business with no fees at https://try.microacquire.com/twist
(27:37) Will SaaS investments continue to be good?
(32:44) What makes Notion so good?
(34:44) AdQuick - Visit https://adquick.com/twist and mention TWIST to get $1000 off your first campaign.
(35:50) What does it mean to play offense? Why should you be playing offense now if you have the runway?
(39:35) Jason Lemkin’s predictions for the next year & advice for capital allocators/investors
(52:25) Are founder secondary sales a red flag?
(1:01:20) Strategies for investors in a down market
FOLLOW Jason Lemkin: https://twitter.com/jasonlk
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood
20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki
Jason Lemkin is the Founder and Managing Partner @ SaaStr, a social community of 500,000+ SaaS founders and a $100M venture fund. In the past, Jason has made investments in the likes of Algolia, Talkdesk, Pipedrive, and RevenueCat to name a few. Prior to SaaStr, Jason was the Co-Founder and CEO @ Echosign, backed by Emergence Capital, Echosign was bought by Adobe and is Adobe Sign as we know it today.
In Today's Episode with Jason Lemkin You Will Learn:
1.) Origins into Venture:
How Jason made his way into the world of venture having sold EchoSign?
What were some of Jason's biggest lessons from his first 4 investments being unicorns?
2.) The Importance of Ownership & Multi-Stage Funds
How does Jason assess the importance of ownership today?
If companies can be $20BN, does ownership really matter?
How does Jason advise founders who have offers from multi-stage funds at seed?
Why does taking multi-stage money at seed result in less pressure for founders?
Does Jason believe that signaling risk from large funds is real, when investing at seed?
3.) Building Your Sales Team
Does the founder have to be the one to create the sales playbook? What are the nuances?
Should you hire a Head of Sales or sales reps first? What should you expect from each?
What are the one criteria that you must look for when hiring your first sales reps?
What are the signals that a sales rep or leader is a 10x hire?
What works when hiring sales reps, 80% of the time?
4.) Boards and VC Value Add:
Why has Jason changed his mind when it comes to boards? Why are some inefficient and some very efficient?
How do the best founders manage their board? How do they bring in their exec team?
What is the right documentation to prepare for board meetings? Why does Jason prefer slide decks over Notion and Coda?
How can leaders use board meetings to direct and goal set with functional leads?
Item's Mentioned In Today's Episode with Jason Lemkin
Jason's Most Recent Investment: Owner
Will rising interest rates decimate startup valuations?
This is Saturday, which means it's not a usual day for us to drop an episode. But what are we if not try-hards at heart? So, we're back today.
What do we have on store for you? I brought Anshu Sharma onto the podcast -- and a Twitter space, so make sure you are following the podcast, yeah? -- to chat interest rates, technology growth, startup valuations, and how they all tie together. Sharma was the right person to have on the show because he's been a big tech employee (Oracle, Salesforce), an investor (Storm Ventures, and as an angel), and he's a founder to boot. So he's been around not just the block, but several in the world of technology over time.
TechCrunch has covered SkyFlow, his startup, a few times including its most recent fundraise.
https://techcrunch.com/2022/02/16/welcome-to-the-post-pandemic-economy-startups/
Sharma finds some of the in-market worry about rising rates harming tech stocks silly. His thesis boils down to the value of growth on a longer time-horizon than what a DCF-tuned spreadsheet might tell you. That said, rising rates will impact some startup inputs, like venture funds in the medium-term, so there was a lot to chew on.
We try to keep Equity pretty high-level, and focused on discrete events. But why have a show if you can't use it to scratch your own itches from time to time?
The pod is back on Tuesday due to an American holiday this Monday. Chat soon!
Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.
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E1147: “Godfather of SaaS” Jason Lemkin on 2020’s cloud software boom, public CEO mindsets, how Zoom conquered the competition & more | Rising Stars of SaaS 8
Check out SaaStr: https://www.saastr.com
FOLLOW Jason Lemkin: https://twitter.com/jasonlk
FOLLOW Jason Calacanis: https://linktr.ee/calacanis
20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Jason Lemkin is the Founder @ SaaStr, now with the $70m SaaStr Fund, Jason has paved the way for the new wave of VC in what I describe the 'platformification of VC'. Jason has led or sourced the first VC investment in some of the fastest growing SaaS companies of today with the likes of Algolia, TalkDesk, Rainforest QA and PipeDrive. Prior to being in VC, Jason was the Co-Founder @ Echosign, leading to the very successful acquisition by Adobe where he oversaw Jason oversaw the growth of Adobe Document Services ARR from $50m in 2012 to $100m in 2013.
In Today's Episode You Will Learn:
1.) How Jason made his way into the world of VC from being a $100m+ exit founder to founding SaaStr and SaaStr Fund?
2.) What is it like for Jason having his own fund vs being part of a bigger fund? What does the investment cheque size say to founders about the fund? Should they be concerned if the investment represents less than 1% of the fund?
3.) What was the fundraising process and environment like for Jason with SaaStr? Is all LP money the same? What differentiated value-add elements can LPs provide fund managers?
4.) Does Jason agree that most VCs do not add value? How does Jason look to add value with his 3 pronged approach? Where does Jason believe that most startups need help and advice?
5.) How does Jason evaluate the micro-VC stage at present? Where does Jason see opportunity? Where does he believe the space is over-heated?
Items Mentioned In Today's Show:
Jason's Most Recent Investment: Automile
As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
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SaaStr 091: Jason Lemkin on Why Hire Fast Fire Fast is BS, Why He Never Invests In Quarterly MRR & Why The Key Is Successful Reinvention
Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise. Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web's most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies.
In Today's Episode You Will Learn:
How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr?
ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands?
Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned?
Jason has previously said that 'founders have to be 110% committed to sales'. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps?
Jason has also previously said that some founders financials are 'simply ridiculous'. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible?
60 Second SaaStr
Why does Jason like it when startups have clients that are not in tech?
What does Jason know now that he wishes he had known at the beginning?
What should SaaS founders look for in their investors?
Why does Jason only invest out of the SaaStr community?
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
SaaStr 090: SaaStr's Own Jason Lemkin on The Specific Characteristics Jason Looks For In Founders? What Levels Of ACV Suggest The Potential For A Unicorn? Why Founders Always Undersell & How You Should Hire Your First Sales Reps?
Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise. Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web's most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies.
In Today's Episode You Will Learn:
How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr?
ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands?
Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned?
Jason has previously said that 'founders have to be 110% committed to sales'. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps?
Jason has also previously said that some founders financials are 'simply ridiculous'. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible?
60 Second SaaStr
Why does Jason like it when startups have clients that are not in tech?
What does Jason know now that he wishes he had known at the beginning?
What should SaaS founders look for in their investors?
Why does Jason only invest out of the SaaStr community?
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
