
Missing OpenAI at $20B: Don't Give Up
3 Startups, 40 Pivots: How to Not F****G Give Up launches TODAY 🚀 labor of love writing this w/@mecolalu and @scribemediaco Story from the book below on how we missed out on investing in OpenAI at a $20B valuation 3 years ago (they're valued at $780B today) 👇
AI Redefines YC's Path to Product-Market Fit
New episode of Uncapped with Y Combinator's leadership, @garrytan, @harjtaggar and @snowmaker. We talked about YC's core value prop, how AI is changing the process of finding product market fit and raising capital, San Francisco and California, the future of YC,...
Pick the Right Sale Type for Your Exit Goals
How much of your business do you want to sell? Should you pursue a minority, majority, or full sale transaction? Founders looking to exit or raise capital have to decide which is the best path to achieve your goals, both...
U of T Startups Raise $10B, Disrupt Global Industries
From AI to quantum chemistry to health tech, startups from my alma mater are scaling globally – raising over US$10B since 2020 and reshaping industries. I’m excited to spotlight six founders from the University of Toronto ecosystem building game-changing companies:...
Seed VCs Act Like Traders, Not True Company Builders
Most seed VCs these days act more like traders than investors or company builders. It's not good for anyone, least of all founders.

Early Bets Pay Off: Intercom Hits $400M ARR
Intercom was in a bad spot a few years ago. We invested well before that and didn't think we'd see a meaningful return. Now they're doing $400M ARR. @eoghan's message to SaaS incumbents: "I know how scary this time is. I want you...
Backing Mission-Driven Founders Defines Version One Ventures DNA
Over the years, we've written blog post after blog post to share how we think publicly and as a tool to refine our investment strategy internally. These 5 posts (link in comments) capture Version One Ventures ' DNA well with...
First Round Capital Offers Year-End Funding Options
Chris, saw that First Round Capital is backing startups and helping them grow. Any chance your business could make use of some capital options towards the end of the year?
AxeleraAI Secures Record €250M EU Chip Funding
. @AxeleraAI has raised the biggest semi round in EU history at $250 million. CEO Fabrizio Del Maffeo told me investor confidence in European chip companies is growing, and talked about commercial expansion, a next-gen chip and the startup's 500...
Every Rejection Is a Step Closer to Funding
Don’t be discouraged by rejections. Every 'no' brings you closer to a 'yes'. Learn from feedback and refine your pitch, using each interaction as a stepping stone towards securing the right investment.

Altruist AI Tax Tool Sparks Custodian Stock Selloff
In this month's latest in #AdvisorTech news. @altruist's launch of a new AI-powered tax planning add-on to its Hazel AI notetaker, which triggered a big selloff in the stocks of established RIA custodians like @CharlesSchwab, @LPL, and @RaymondJames: https://t.co/GaoXPwW9F3 And other...
Avoid These 5 Common Mistakes Aspiring VCs Make
5 mistakes aspiring VCs keep making (and nobody tells them): 1. Leading with resume instead of edge 2. Thinking all VC firms are the same 3. Networking to find a job instead of to add value 4. Not translating operator experience into investment language 5....
Sequoia Fast‑tracked $75M Series B After Deep Customer Vetting
A look inside @getserval's Series B, the #1 company on @harmonic_ai's Hot 25 list last quarter
Bootstrapped SaaS Thrives on Trust, Not Code
Gah such a great take. I don’t invest in large SaaS plays, but on the micro end, especially for bootstrapped founders, it’s still a fantastic place to build.
OpenAI and VCs Will Fill Military AI Void
If anthropic doesn’t want to do military tech, you can be sure that OpenAI (or another foundational model), will bend over backwards to provide whatever the department of war wants. And the department of war/defense doesn’t need to accept any...
Early Bets Win; Amazon’s Late Entry Costs Billions
Early positioning beats late capital every time. Amazon just invested $50 billion in OpenAI for 6 percent ownership and distribution rights. Microsoft invested $13.8 billion starting in 2019 and owns 23.5 percent with exclusive IP, revenue sharing, and API control locked through...
Prioritize Growth and Brand Over Early Profit
Profitability shouldn't always be the primary goal in the early stages. Sometimes, investing in growth, user experience, and brand reputation is more important than immediate profits. Play the long game. ✨
Company Secures Record Private Funding Amid Cofounder Lawsuit
Remarkable that a company raises largest private round ever, while in the midst of being sued by a cofounder who also happens to be the world' richest man.
Efficiency Revolution: Companies Will Trim Workforce by Half
Could you operate your company with half the people? Jack Dorsey’s announcement yesterday, reducing Block’s headcount from 10,000 to 6,000, should provoke this question in every management team. The stock surged 24%. Dorsey’s memo framed it as inevitable : Within...
OpenAI's Record Funding Rattles AI Giants and Software Stocks
There's a new kingmaker in AI... OpenAI raises the largest private funding round in history and two of the biggest backers ($NVDA and $AMZN) are down to flat today. Meanwhile a blog post from Anthropic sends software stocks swinging
Storytelling Beats Metrics in Early-Stage Fundraising
Metrics matter. But in early-stage fundraising? Storytelling matters more. In Ep. 234 of The SaaS CFO Podcast, Helen Hastings shares why vision + narrative win investor conviction. Listen here 👇 YouTube: https://t.co/BnQYh8fzzR #SaaS #Fundraising #Startups https://t.co/zRSXoqqM2z
Ask Rejected Investors for Immediate Feedback to Refine Pitch
Seek feedback from investors who pass on your pitch. In fact, ask for feedback right there on the call (much easier than trying to get it via email later). Use it to improve your approach and strengthen your next presentation. Constructive...
LLM Boom to Yield $10B Profit by 2031
Can someone make me an analysis for the jcurve being created by LLMs and supporting companies (data centers)… which should be $250b today… Assume $250b more invested over next 4 years Then assume $10b in profits in 2031 and 50%...
Watch Webinar Linking Top 100 Biotech VCs Insights
Here's the link to watch yesterday's webinar on venture capital, a companion to this year's top 100 biotech VCs list with @ChrisDoko Lots of positive feedback here. Post your thoughts. https://t.co/c16y04mFsD
OpenAI Poised for $10 B Infusion, $850 B Valuation
As noted in Axios Pro Rata: OpenAI expected to add another $10 billion to the round, which would bring it to $120b at an $850b post-money valuation. Would be from sovereigns and other fin investors (including existings). https://t.co/xDMSkiZRiR

OpenAI Secures $110B Funding, Targets $600B Compute
With backing from Amazon, Nvidia, Softbank -> OpenAI raised $110B at a $730B pre-money valuation, up from $500B in a secondary financing in Oct.; Amazon invested $50B, Nvidia and SoftBank invested $30B each $600B -> "OpenAI has been telling investors that...
Big Seed Rounds Aren’t Irrational, They Reflect
A mini rant about seed VC models and pricing. Seed VC's lament that rounds have gotten so big and varied and there is no definition of a seed round anymore. They tend to suggest this is a signal of irrational...
Tencent Pulls Funding as Highguard Misses Launch Targets
Bloomberg reports that Highguard devs thought they had more runway but Tencent seemingly pulled funding when it failed to hit launch goals.

Bluprynt Secures $4.25M Seed, Bridges Compliance to On‑Chain
Truly big news today: I’m delighted to share that my startup @blupryntco has completed its oversubscribed $4.25m seed raise. Thanks to an all star roster of investors including @valorcapgroup @CultivationCap @RobinhoodApp @cbventures @QuonaCapital @FlourishVC @SelahVentures and Kazea for joining...
Bill Gurley Missed Google’s 10,000x Gain, Shares Lessons
the amazing story how Bill Gurley @bgurley passed on Google––and missed a 10,000x return🤯 i think he'll be all right. And you will too if you read his new book 🔖"Runnin' Down a Dream"... https://t.co/fiRcxsWair
Encord Secures $60M Series C to Power Physical AI
Congrats to @encord_team on their $60M Series C! Encord is building the AI-native data layer powering physical AI, helping 300+ teams manage and align massive volumes of multimodal data as robots and autonomous systems move into real-world deployment. https://t.co/qfx0F6vHQh
Einride Secures $113M PIPE Ahead of IPO Debut
NEW: Self-driving truck startup Einride raises $113M PIPE ahead of public debut The fun thing about having covered so much of the tech landscape is jumping in on story coverage outside your beat for your colleagues when they're OOO https://t.co/YpkUAlfdhU via...
SambaNova Skips Intel Acquisition, Secures Funding and Partnership
.@SambaNovaAI cancelled plans to be acquired by Intel, instead raising an oversubscribed Series E. SN's CEO and chief architect told me about a new multi-year tech and go-to-market partnership with Intel, and SN's new silicon for multi-agent workflows: https://t.co/JLMl9PIUGk
Biotech VC Webinar Launches with Top Experts, Thousands Registered
We'll be gearing up today's webinar on biotech venture capital at the top of the hour. Great guests, great topics. If this is a central issue in your life, tune in. Thousands have signed up already. https://t.co/c16y04mFsD
Seed Pursues the New, Avoids Over‑Specializing in Trends
"Seed is not small venture. Its sole purpose is to navigate the new." This is one of the reasons why we've never over-indexed into any single category or trend. Our goal is to catch the "new".
Sequoia India Unit Torn Apart by Power, Profit Dispute
Another great piece from @followthemani for @NewcomerMedia Sequoia’s Former India Unit Rocked by a Bitter Split Over Power & Profit Shares https://t.co/gl1dPgdIm3
Our Portfolio Is 80% B2B, Not Consumer.
Recent convo with a founder: "Weekend Fund primarily invests in consumer, right?" I've heard this before. I love weird consumer, but in reality 80% of our investments are B2B or prosumer. Examples: American Operator (big boring b2b), Certn (enterprise infra), Deel (fintech), Extropic (deeptech...
OrbiMed Leads Top Five Biotech VC Dealmakers
Always fun to look over @JohnCendpts annual list of the top 100 most active VCs in biotech for the past year Top 5, by # of rounds: 1. OrbiMed 2. RA Capital 3. GV 4. General Catalyst 5. Catalio Full list & analysis is live...

Revolut IPO Sparks Unprecedented Fintech VC Liquidity
We are going to see previously unheard of liquidity in fintech VC following the @Revolut IPO. "The firm is targeting a valuation of at least $150 billion through any listing." https://t.co/mos6kPJDYO
AI Forces VCs to Rethink Sourcing: People Remain Moat
Venture capital is not immune to AI disruption. So we asked ourselves the hard question: If we were starting Harlem Capital today, what would we do differently? We spent three days in a house rebuilding our sourcing strategy from scratch. We walked away...

Success Attracts Talent; Failure Repels Potential Partners
In this case, the founders achieved something pretty remarkable. So imagine what he would do if the founders actually failed. Who would want to work with someone like that? https://t.co/mCAucKKUoo

Handshake's Pivot Targets $1B Revenue in 2024
Incredible founding story and astonishing pivot into a new business at Handshake. A conversation in Dec 2024 led to a new business that will do $1B+ this year. CEO @GarrettLord with Upfront’s @nickbkim https://t.co/MRUtbjzcA1
SaaS Apocalypse? Market Hype Meets Skeptical Reality
Is the SaaSpocalypse upon us?! Markets went bananas after this Citrini article was published — but is this legit? Deedy Das isn’t so sure… Which businesses do you think are going away?
CFO Guide: Guardrails for Secondary Tender Offers
How much money is too much money for employees to take out in a secondary? What are the appropriate guard rails to run a tender offer as a CFO? And is the rise of SPVs helping or hurting the reputation...

OpenAI's $100B Raise Defies Profit Logic
OpenAI is closing a ~$100B funding round despite being unprofitable. On paper, it makes no sense... But here’s what everyone’s missing:

From Doorbot to Ring: $1B Dream in 2018
“Back when I sold Ring in 2018, $1 Billion was a lot of money” @JamieSiminoff and @hametwatt at the Upfront Summit - Hamet came up with the name Ring (instead of Doorbot) and Jamie wanted a four letter domain like...

Guard Your Cap Table: Success Attracts Detractors
Founders, know that even if you build a world class product and achieve an outcome most can only dream of, there will still be people that try to tear you down. Be very careful with who you allow onto your...

Investors Value TAM Growth and Adjacent Market Expansion
Thomas Laffont of Coatue doesn’t care about the size of your TAM. He cares about how the TAM is growing, and what adjacent TAMs you can grow into. Example - Uber grew the Taxi market then moved into...
Founders Beware: ROFR Clauses Can Block Future Exits
For minority investors to include protective provisions within their purchase agreements is common practice, but one provision that founders should be particularly aware of is the right of first refusal (ROFR). A ROFR clause places an obligation on the company...
Rare Glimpse Into Secretive Thrive's Performance Data
got my hands on Thrive's performance. secretive firm so this provides a rare snapshot of how they're doing https://t.co/5dbvPfrUF1