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Founding Partner at Underscore VC, Executive Fellow at Harvard Business School
Boston, Massachusetts, United States
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147K followers
500+ connections
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About
See https://underscore.vc/team/michael-skok/ for professional profile
See https://mjskok.com/about for personal profile
Articles by Michael
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Are you able to travel? Do it!
Are you able to travel? Do it!
Travel is the best education imho. It broadens our perspectives, helps us become more accepting of other cultures and…
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24 Comments -
Startup Founders: What can you learn from Uber's Q1 results?May 2, 2023
Startup Founders: What can you learn from Uber's Q1 results?
As an investor, it's my job to look beneath the surface when a company reports results. Following their Q1 23 results…
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13 Comments -
Succession... The King of SustainabilitySep 12, 2022
Succession... The King of Sustainability
Last week I shared this post on the passing of Queen Elizabeth: Many of us are feeling great sadness for the loss of…
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6 Comments -
Would you take a billion-dollar buyout?Oct 1, 2019
Would you take a billion-dollar buyout?
Would you take a billion-dollar buyout? My answer was “no”! Yet, as an Acquia board member, I was happy to vote “yes”…
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17 Comments -
How do you Create a Win-Win-Win Acquisition?May 8, 2019
How do you Create a Win-Win-Win Acquisition?
It starts with customers and ends with customers. Let’s share an example: Acquia, the open source digital experience…
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5 Comments -
As you go back to work, don't...Jan 2, 2019
As you go back to work, don't...
As you go back to work today, don't forget to take a moment to enjoy the journey. If you're like me you're all too…
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33 Comments -
Why we're investing millions in an awkward teenager...Dec 31, 2018
Why we're investing millions in an awkward teenager...
With Underscore VC's newest fund just closed oversubscribed at $140M, we’re doubling down on our investment thesis and…
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9 Comments -
What can a startup learn from a $24B business that reinvented our industry?Oct 12, 2018
What can a startup learn from a $24B business that reinvented our industry?
As a startup, what would you like to learn from a a twenty four billion dollar business built in 12 short years while…
1,141
41 Comments -
Health is wealth! Share it!Sep 15, 2018
Health is wealth! Share it!
I've cracked my skull, broken 3 legs, fractured my wrist and elbow, nearly lost a finger, been operated on multiple…
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5 Comments -
What do Tech CEOs Want to Talk About?Jun 23, 2018
What do Tech CEOs Want to Talk About?
3 insights from startup to multi-hundred million dollar business leaders. The Underscore Core Community is a curated…
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28 Comments
Activity
147K followers
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Michael Skok shared thisGot a minute? No? Good - because you only get 6 seconds. That’s all it takes to lose your next hire, customer, or investor. Most founders don’t realize when it happens or why. Watch from 4:40 in this clip, and you’ll understand. 👉 https://lnkd.in/e7qs55RB If you want two simple frameworks you can learn in 2 minutes and use for a lifetime, you can find them here : 👉 https://lnkd.in/eqV685NM Did this help you seize your story? If not, please share how it can be improved for others to benefit... #Founders #Startups #Entrepreneurship #StartupLife #EarlyStage
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Michael Skok shared thisSix seconds. That's how long you have to catch their attention. Then sixty to convince them. The investor. The customer. The recruit you need. You open with: "We're an AI-powered platform that leverages machine learning to optimize..." Phones out. Eyes glazed. Gone. Everything you've built, the breakthrough, the team, the vision, hanging on a story you aren’t telling. After seeing tens of thousands of pitches personally and hundreds of thousands collectively at Harvard, we’ve all realized we've missed the point: encouraging pitch competitions and demo days, forgetting the crucial element. This has to change, ASAP! The pattern is clear: the best founders and entrepreneurs often don’t get the attention they deserve, let alone the support they need. Not because the opportunity isn't real. Because the story isn't. But here's what those decades also revealed: the same simple story structure runs through Aristotle, Pixar, TED Conferences and billion-dollar raises. Once you see it, you can use it in every pitch, hiring conversation and customer meeting. You can learn it in minutes and reuse it for life. This Monday at Harvard Innovation Labs, together with Harvard Business School Foundry, we will work through that structure live on real founder stories. If this hits a nerve, comment below to get access as follows: 🎟️ "VIP" - with your email, to request join in person as my guest - spots are very limited 💻 "Zoom" - with your email, if you’d like the private link to join live at 4:30pm ET Monday - spaces are less limited but not infinite! 📚 "Startup Secrets" - to get the link to the frameworks and practical canvases to apply them to your venture when we release them next week. Or if you're a Harvard University student just register here https://lnkd.in/eHyRqwgm #StartupStorytelling #Founders #Entrepreneurship #HarvardInnovationLabs #StartupSecrets Underscore VC Harvard Business School Harvard University Harvard Launch LabEvent: Startup Secrets: Seize Your Story with Investor Michael Skok |…Event: Startup Secrets: Seize Your Story with Investor Michael Skok |…
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Michael Skok shared thisCan an AI truly mentor a founder -- or is real mentorship something only humans can offer? Brad Feld and I will be holding a virtual chat on this topic next week, live here on LinkedIn. In advance, I'm taking some of my own medicine and asking you to tell me all the reasons why you would **not** use an AI mentor. (This comes from one of my favorite Startup Secrets: ask your customers all the reasons they would _not_ buy your product if you want to build a meaningful roadmap.) Just drop one reason below -- the sharper the critique, the better! To make this more real, here's the link to a personal beta version of Michael Mentor, an AI developed in my work with Harvard Business School Foundry team: 👉 https://lnkd.in/e-Kafr_H A more advanced Foundry version is coming soon. In the meantime, try asking Michael Mentor for some startup mentorship or coaching. Here are a few starter questions you might try: 🤔 "What's my riskiest assumption?" 💡 "How do I know if I've found a real problem?" 🧭 "What's something I'm not seeing that could sink my startup?" All I ask is that you don't take my AI's guidance without pausing to think for yourself. Because mentorship -- human or AI -- only works if we think for ourselves. As I like to remind my students: > "There's no good advice until it becomes your own advice." Share your thoughts below -- your feedback will directly shape the next version. Otherwise, mark your calendars for **Thursday, October 16, 12:00--1:00 p.m. Eastern Time**, when Brad and I will be discussing why we believe real-world mentorship remains vital. We'll also share a few hilarious stories of what our AIs have told people during testing! https://lnkd.in/eD-Wg_5d Oh, and by the way, for the first 50 people who try Michael Mentor and give feedback, it will be my pleasure to give you a copy of Brad's wonderful new book "Give First: The Power of Mentorship." Let's explore what the #futureofwork and #mentorship in the age of #AI can teach all of us #founders. #entrepreneurship #startupsecrets #innovation
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Michael Skok shared thisDo you have an idea? How much does it matter to you? Enough to turn it into a startup? If so come and join us tomorrow Harvard Innovation Labs as I learn what it really takes from the students who are busy inventing the future. And if you can't make it but want to get the materials from the workshop. Leave your name and email address in the comments. 🙏 #innovation #entrepreneurship #startupMichael Skok shared thisIf ideas don't matter, what does? Join us tomorrow at the i-lab for a special interactive workshop with Michael Skok, founding partner at Underscore VC, and Rebecca Xiong, PhD, Managing Director of Programs and Engagement at the i-lab. Discover why ideas are just the beginning, and learn what truly drives venture outcomes—validation, execution, and more. Don’t miss this opportunity to gain expert advice on navigating early-stage challenges and building impactful ventures! RSVP here: https://lnkd.in/e-BX3x8P
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Michael Skok shared this🥳 What a wonderful story and reminder that entrepreneurship is so often about the mission and the people behind it. Congratulations to the great team at Shield AI and you too Molly for charting your own course and avoiding VC dogma.Michael Skok shared thisEat your heart out Mav and Goose: Dorm Room Fund company Shield AI announced their $240M Series F at $5B post this week to support making fighter jets fly themselves. We backed the team as one of their first investors, before their seed round in 2016, when Brandon Tseng was still a recent Navy SEAL and student at Harvard Business School. One of my favorite highlights from the investment memo was this quote from the founders, "The team’s biggest concern is fundraising, 'the VCs we’ve met with have shied away from defense because of misconceptions' around how long it takes to win contracts in that end market". Oh how far we've come! Shout out to Riley Soward and Vesal Yazdi who first introduced Brandon, Ryan Tseng 🇺🇸, and then CTO Andrew Reiter. Just goes to show that our thesis that fellow classmates-- in this case, Vesal-- know better than just about anyone who the best builders are in their peer set. Congratulations, Bandon, Ryan and Team ShieldAI! What a ridiculous journey.
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Michael Skok shared thisAI Agents will require reasoning. But where will that come from? Are you an innovator building it? Or an entrepreneur looking to enable it? Richard Lily Gabrielle Chris Brian are curious to collaborate on #appliedai #agenticai #futureofaiMichael Skok shared thisEveryone's talking about AI agents, but who are the builders in this space to watch? Underscore VC created an 𝗔𝗜 𝗔𝗴𝗲𝗻𝘁 𝗜𝗻𝗳𝗿𝗮𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲 𝗟𝗮𝗻𝗱𝘀𝗰𝗮𝗽𝗲 spotlighting the startups building the infrastructure for an “agentic” future of AI. It’s going to be an exciting decade as new AI agents empower us with 𝘀𝘂𝗽𝗲𝗿-𝗽𝗿𝗼𝗱𝘂𝗰𝘁𝗶𝘃𝗶𝘁𝘆, from advanced orchestration platforms to self-authenticating API-less browser tooling, these companies are forming the backbone for the computing transition we believe could create as much (or more!) value as the shift to the internet or cloud. Our goal is simple: help everyone laying the groundwork for tomorrow’s agent-driven software get to know each other and put a few waypoints on the map about how we see the “agent stack” shaping up. What do you think? And who did we miss? Let us know! 🟨
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Michael Skok shared thisStartups, do your partners and customers have proprietary data you can bring safely into your AI workflows? TetraScience and Patrick Grady are exemplifying why it’s important to focus on the outcome not the technology for AI… #appliedai #futureofai #startupMichael Skok shared thisScience-tasked AI requires an unfathomably large data access channel that is as diverse as it is controlled. That's why TetraScience teamed up with Snowflake to enable data science teams to work with scientific data in new ways, driving a scientific AI revolution. The partnership news follows on a string of recently signed partnerships between TetraScience and Google Cloud, Databricks and NVIDIA, each of which support the startup's ambitions to transform siloed, proprietary and unstructured scientific data so it can be used by engineers and scientists for AI and data apps to improve each step in drug development and manufacturing.TetraScience, Snowflake Put Heads Together For Scientific AI Biopharma Brain BoostTetraScience, Snowflake Put Heads Together For Scientific AI Biopharma Brain Boost
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Michael Skok shared thisDo mergers work by math ? If so here’s mine for this one: 1+1*Shishir = Magic Full disclosure - I’m a biased Coda investor, user and now Grammarly investor by outcome. But most of all I believe in people and Shishir, Alex and the whole team at Coda have proven themselves to be superb listeners who care to understand and serve their users needs. My 2 cents - If you’re a customer of either company, get further invested - you’re in for a rare treat! 🥳👌👏Michael Skok shared thisBig exciting announcement: I’m excited to share that I’ve signed the agreement for Grammarly to acquire Coda! And I’m honored to lead the combined companies as CEO. I share much more details on how this came about in my blog post, but as I chatted with the leaders at Grammarly, I realized that both companies have arrived at remarkably similar views of the future. One where AI will redefine every business application and workflow, reinventing productivity as we know it today into a place where humans and AI work together everywhere you get work done. Grammarly is an amazing platform — with over 40 million daily active users, I see Grammarly as one of the world’s most ubiquitous AI assistants. We have a broad roadmap of how we’ll bring the products together. First, we’ll be working on making Grammarly’s ubiquitous AI assistant even “smarter” and “more helpful” by adding the context of Coda Brain. And second, we’ll be working on unifying Coda Docs and the Grammarly Assistant to provide users with a flexible home for users to work. Longer term, we have much grander plans for how we’ll weave together our products to build the AI productivity platform for agents and apps. I think it will feel like a dramatic acceleration for the Coda product and mission, helping to reach millions of users and help redefine the future of AI-driven productivity. It’s an important milestone, a big transition for the company. I couldn’t be more excited about it! Read more at: https://bit.ly/49DVQGx
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Michael Skok reposted this🧬 Congrats to Patrick Grady, Siping Wang, and the TetraScience team on the unveiling of their partnership with NVIDIA today as the reference stack for scientific AI at global pharma companies. In their mission to accelerate scientific advancements and workflows, the data needs to sit somewhere, and the complexity of the vertical demands a specific type of scalable Scientific Data and AI Cloud. “One of the most significant ways AI can benefit the pharma and life sciences industry is by enhancing complex scientific experiments and lab data, reducing time and costs for managing them,” said Kimberly Powell, vice president of healthcare at NVIDIA. “We’re working with TetraScience to innovate and integrate generative AI and agentic workflows for knowledge extraction, relationship discovery, and reasoning, helping the industry get the most out of its data.”Michael Skok reposted this🔬 Thrilled to announce TetraScience's new collaboration with NVIDIA to accelerate scientific AI adoption across life sciences! We're tackling a $1.5T industry challenge: transforming siloed scientific data into AI-driven insights and scientific use cases that can transform drug discovery, development, manufacturing, and QC. By selectively pairing NVIDIA's domain-specific AI models and compute infrastructure with the Tetra Scientific Data and AI Cloud, Tetra is creating a “factory model” approach to producing targeted, high-impact scientific AI use cases at an industrial scale across the biopharma value chain. Our initial focus includes transformative applications like lead clone selection, where we've already demonstrated the potential to reduce traditional timeframes by 80%. Quality testing can be completed twice as fast using AI to reduce deviations and accelerate investigations. AI in quality assurance can shorten lead times and enable real-time product release. Read the full announcement: https://lnkd.in/eEjBRgFb #ScientificAI #LifeSciences #Innovation #NVIDIA #TetraScience #DrugDiscovery
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Michael Skok reacted on thisMichael Skok reacted on thisBoundaries and Bridges: International Relations in the Age of AI / Sınırlar ve Köprüler: Yapay Zeka Çağında Uluslararası İlişkiler The field of International Relations has always been shaped by boundaries and bridges. Boundaries represent sovereignty, security, and identity. Bridges represent diplomacy, trade, and shared human judgment. In the age of AI, both concepts are becoming even more critical. AI is transforming how states process information, perceive risks, and make strategic decisions. Yet it does not eliminate uncertainty, remove human responsibility, or replace moral courage. This is where the concept of "bounded rationality" becomes highly relevant. It was formulated by the late Nobel laureate Herbert Simon—a brilliant mind I had the privilege of knowing during my years at Carnegie Mellon University as a graduate student and faculty member at the Robotics Institute. Professor Simon reminded us that humans do not decide with perfect information or unlimited time; we operate under strict constraints, limited foresight, and uncertainty. In geopolitics, this is the daily reality of statecraft. Yunus Emre, a 13th-century Turkish poet from the heart of Anatolia, beautifully captured this human struggle with knowledge: "Knowledge means to know yourself, heart and soul / If you have failed to understand yourself, then all of your reading has missed its call." If we accumulate endless algorithmic data through AI without understanding our own human biases and limitations, our technological "reading" of the world remains hollow. AI may help us bridge some of these gaps. By analyzing data and modeling complex systems, we are moving toward bridged rationality. But bridged rationality is not unbounded. AI is a tool to support human judgment, not replace it. Strict boundaries remain essential. The central question is what kind of institutional wisdom we build around AI. Long before modern computing, Al-Farabi, the foundational Islamic philosopher of Turkic origin, noted that leadership cannot thrive on raw capabilities or power alone. True statecraft requires the discernment to choose virtue over what is merely expedient. The future belongs to those who combine technological intelligence with restraint. As the great mystic Rumi—from my ancestral city of Konya—reminded us: "The spirit is a majestic bridge, spanning the gulf between the intellect and the divine." In our technological pursuit, we must ensure our digital bridges do not collapse into mere calculation, but instead span the gap toward a more humane understanding. Bounded rationality taught us humility. Bridged rationality may teach us collaboration. But only wisdom can teach us which bridges to build, which boundaries to respect, and when to pause before crossing. Photos: Captured by Halil Kulluk over the Bosphorus. #Bridges #Borders #AI #InternationalRelations #BoundedRationality #BridgedRationality #RoboticsInstute #CarnegieMellon #Philosophy #Farabi #Rumi #YunusEmre
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Michael Skok reacted on thisMichael Skok reacted on thisAfter 10+ years building Underscore VC, I'm stepping back from my day-to-day role at the firm to start an AI infrastructure company. Underscore has been the work of my career. We started with a thesis, a handful of high-conviction LPs, and the belief that venture could be done closer to founders than the industry was doing it. What grew from there — the portfolio, the team, the trust founders placed in us — has been nothing short of magic. I'm deeply proud of all of it. The firm is in extraordinary hands. Lily has been the heart of Underscore from nearly day one, and the partnership she's leading now is sharper and more ambitious than ever. Underscore's best decade is ahead of it, not behind it. But the pull to build a company to serve this moment is too strong to ignore. We are living through the most consequential infrastructure shift of our lifetimes, and there's a layer — the connective infrastructure between AI systems and the messy real-world workflows they're trying to automate — that doesn't exist yet, and won't unless someone builds it. Too much needs to exist for me to only watch it happen. Earlier this week I published a framework for thinking about which moats actually compound in the AI era. The deepest tier — the unwritten context that lives in the handoffs and in the reasons nobody writes down — is where I think the most important infrastructure of this era gets built. So I'm going to go build it. More on the company when we're ready. I'll stay close to the Underscore team, our LPs, and our founders. Until then, we'll be mostly heads down with our first customers. I'll be in Boston for Tech Week — coffee's on me if you're around. To our LPs, our founders, Michael and John who started this with me, Lily and the partnership carrying it forward, and the generations of Underscore still to come — thank you. For everything.
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Michael Skok reacted on thisMichael Skok reacted on thisThrilled to share that Classy AI has been selected as a semifinalist in the Harvard President’s Innovation Challenge! It takes a village to build a venture and there is no better village than the Harvard Innovation Labs. Thank you to Rebecca Xiong, PhD, Peter Gladstone, and Ashley Olafsen for their support, guidance, and perspective. Grateful as well to Paul Hayre. Harvard Grid events were instrumental in connecting with fellow founders and advisors. Thank you to N'kyla E. for her inspiration, insight, and expertise. To Lisa Águeda for her IP counsel. And to Michael Skok for always bringing compassion, empathy, and kindness to the table. As technology transforms what’s possible, Classy AI is built to restore belief in human capability — inspiring students to see that they remain the most powerful force shaping the future today.
Experience
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Founding Partner Emeritus
Underscore VC
- Present 10 years 10 months
Greater Boston Area
Underscore is a Boston VC firm that backs bold entrepreneurs from Seed to Series A with an aligned Core Community designed to fit each startup's unique needs.
The Underscore team is a diverse mix of seasoned investors, operators, and entrepreneurs. Above all else, we’re listeners and learners who are united in our belief that it’s all about you and your mission. Entrepreneurs humble us, and we’ll do everything in our power to remove the barriers that stand between you and your success. -
Harvard Business School
10 years 10 months
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Executive Fellow
Harvard Business School
- Present 3 years 10 months
Cambridge, Massachusetts, United States
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Entrepreneur in Residence
Harvard Business School
- 7 years 1 month
Greater Boston Area
Mentoring, learning and teaching at HBS and Harvard i Lab
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Co-Lead Investor and Board Member
Salsify
- Present 13 years
Greater Boston Area
See http://www.linkedin.com/today/post/article/20130912113622-1893586-just-do-it-right-from-the-start for details.
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Principal Owner
Startup Secrets | Michael J. Skok
- Present 14 years 6 months
Boston, Massachusetts, United States
Startup Secrets is a program for YOU the founders, entrepreneurs, and builders who will change our world for the better.
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Lead Investor, Board Member
Moltin
- 5 years 8 months
Greater Boston Area
Moltin led the movement for "headless" commerce, and was acquired by ElasticPath. Moltin's CEO and technology are now at the core of ElasticPath's products and roadmap.
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General Partner
North Bridge Venture Partners
- 12 years
Michael Skok, Partner, helps take software companies from concept to completion – just as he did as an entrepreneur and CEO. Michael has a reputation among entrepreneurs for acumen in many spheres: people, technology, and markets, but most of all, company building.
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CEO, Founder
AlphaBlox
- 5 years 1 month
Michael co-founded Alphablox whose team defined the market for Analytical Applications, now a multi billion dollar market. After building a trusted brand with a loyal customer base among leading global 1000 companies, AlphaBlox was acquired by IBM.
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Chairman and CEO
European Software Publishing
- 7 years
Michael founded European Software Publishing (ESP) which pioneered the off balance sheet model for building software companies in Europe. Thanks to a strong management team, 4 of these publishers were acquired by Siebel, Platinum, Filenet and Banyan and two went Public. This included the team that built Symantec UK into one of Symantec's most profitable international businesses while managing many acquisitions through to Symantec's IPO and enduring industry status.
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Publications
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Startup Secrets
Harvard i Lab
See publicationA workshop series in conjunction with the Harvard i Lab to help startups get "Unfair Competitive Advantage".
Recommendations received
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LinkedIn User
“You want Michael Skok on your team when you are building a billion dollar company. Michael is a brilliant strategist that can execute on big ideas. From the moment I met Michael I knew that he was someone that I could trust and learn from and I am fiercely proud to be working with him to grow Apperian.”
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KEVIN RAPER
The Fulcrum; Work • 3K followers
Most founders treat warm intros like a nice-to-have. They think if the deck is strong enough, the right investor will notice. They’re wrong. Investors don’t have a filtering problem. They have a trust problem. Every week, they see hundreds of decks. Some great. Many decent. A few even brilliant. But that’s not the bar. The real question isn’t “Is this startup promising?” It’s “Do I trust this founder enough to take the call, stake my reputation, and possibly invest?” That’s what a warm intro solves. It reduces the trust gap. When a credible founder, respected operator, or trusted LP vouches for you, you’re no longer a stranger in someone’s inbox—you’re a filtered signal from someone they already believe in. • Without that credibility transfer, the burden of proof falls entirely on your deck. And no matter how strong it is, most investors won’t roll the dice if no one is standing behind it. But here’s the part most people miss: You don’t get warm intros. You earn them-long before you need them. Because warm intros aren’t just about access. They’re about shared experience, long-game relationships, and quiet reputational equity. The founders who raise well are the ones who tend the garden: They help others before asking for help. They’re kind when no one’s watching. They make time for feedback, referrals, second looks. They show up generously—and consistently. Fundraising isn’t a visibility game. It’s a credibility game. And credibility isn’t built in the room. It’s built over time. This post is a primer on that blind spot: What warm intros actually signal to investors. Why founder-to-founder intros beat cold outreach every time. How to turn a “no” into long-term trust. Why using brokers or “fundraising middlemen” almost always backfires. How to build a reputation that makes capital feel like a shared bet—not a leap of faith. If you want to raise smarter-and faster-understand this: Warm intros aren’t about playing favorites. They’re about reducing friction in a world where trust is scarce and time is shorter. And the best time to start building trust? Before you need it. #startups #fundraising #venturecapital #warmintros #founderlife #networking #trustdriven
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Arjun Malhotra
Good Capital • 3K followers
Growth and profitability are not opposing forces. If anything, they're sequential. Once your unit economics work - every additional customer can spread fixed costs thinner, every transaction can make ops more efficient, and every bit of volume can give you better terms with suppliers. Solving for fundamentals will ensure growth makes you profitable, and doesn't become the thing that keeps you from it. Shreyans wrote a great piece on it, link in comments.
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Paul Santarelli
PitchBook • 1K followers
PitchBook's quarterly Venture Monitor report shows a market that is beginning to move again, but unevenly. These are discussions we have with customers every day and we have seen these trends play out across the market. But the numbers certainly speak for themselves. In 2025, AI accounted for about 65% of total deal value and nearly 40% of deal count, driving a highly concentrated environment where 50% of deal value went to just half of 1% of deals. Deal activity increased across every stage, with early-stage and first financings nearing 2021 highs, even as fundraising and liquidity remain constrained. It seems that opportunity is returning, but selectivity and differentiation matter more than ever. As always, we strive to ensure we are helping our clients across the private capital market ecosystem navigate the current environment. http://spr.ly/6045CFwD5
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Steve Vassallo
Foundation Capital • 16K followers
Boards are supposed to help founders. Over the past 19 years, I've watched many trap them instead. As companies scale, many boards turn from insight to oversight and stop doing what founders actually need: Help making big, hard decisions. Early boards tend to be small, the board members are close to the business and highly invested in it. They argue from first principles. They help founders think. Later-stage boards often look more impressive on paper - they have more independent directors, committees and process. Somewhere along the way, collective problem solving gets replaced with oversight. The board shifts from helping the CEO make better decisions to monitoring decisions that have already been made. Strategy discussions get safer, real debate gets rarer and meetings become more about risk management than judgment. This usually coincides with the introduction of more professional board members. For better or worse, they often optimize for governance, optics, and liability management. That’s their job. But it’s not always what the company needs in moments of real uncertainty. Then, CEOs stop using them as thought partners. That’s a problem. So what should founders do? A few principles that help: • Keep the board as small as you can for as long as you can • Add directors for new insight they bring, not what boxes they check • Treat board seats like senior hires, not trophies • Design meetings for debate rather than reporting • Be explicit about when you want input vs approval Good boards should improve decision-making. If your board isn’t making you think harder, it’s probably not doing its job.
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Rajiv Vaishnav
Cornerstone Ventures (CSVP… • 17K followers
Excellent articulation by our partner Deepak Kumar on the 𝐂𝐨𝐫𝐧𝐞𝐫𝐬𝐭𝐨𝐧𝐞 𝐕𝐚𝐥𝐮𝐞 𝐏𝐫𝐨𝐩𝐨𝐬𝐢𝐭𝐢𝐨𝐧 𝐒𝐭𝐚𝐜𝐤. This framework not only helps us evaluate where solutions create defensible value, but also serves as a practical playbook for founders to scale with durability and competitive edge. A must-read for entrepreneurs navigating their growth journey. 👍 Cornerstone Ventures
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Dietmar Walter
Widgit • 605 followers
As a board advisor, I’ve seen this pattern play out all too often: small to mid-sized technology businesses getting into real trouble not because of a bad product or a broken market, but because the executive team underestimates the importance of effective board communication and board relationship management. A business model pivot is one of the most critical and fragile periods in a company's life. Even in such high-stakes situations, I have witnessed executive teams mismanaging their board relationships, with expensive consequences for financial and human capital. I saw a profitable, cash-flow-positive SaaS business try to move from B2C to B2B, having already: • redirected resources • shifted management attention • started execution …all before the board had been properly engaged and crucially without a business plan. The initiative was blocked. Trust and goodwill were burned. The executive team had to go back to the drawing board, develop a detailed business plan, and restart discussions from scratch. Exactly what should have happened before resources were redeployed. Eventually, the board approved to give the executive team a 12 months window with a defined budget, setting expectations around traction and evidence. A year later, the B2B experiment had failed, the core business had suffered from loss of focus, and the executive team changed. Ironically, a renewed focus on the core business, with fresh leadership and discipline, put the company back on a growth path. Three lessons stand out: 1. Boards don’t like surprises, trust is built through early engagement 2. Pivots need real business plans, not conviction alone 3. Focus is a strategic weapon, especially in scale-ups Boards are not there to block ambition. They’re there to protect the long-term health of the business. Executive teams that treat the board as a thinking partner, not an approval hurdle, make better decisions and move faster in the long run. More details about this topic in the article below https://lnkd.in/ep2MDvM9
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Justin Knorr
Cada Partners • 4K followers
The gap between SBIR and venture funding is the narrowest it's been in 44 years. Reauthorization created a new award tier up to $30M. 0% equity. Requires a prior Phase II award + a 1:1 match (private capital or non-SBIR government funding) + a federal customer signaling intent. Closer to a co-investment round than a grant. Founders winning these in 2028-2029 are entering the Phase I pipeline right now. I sat through the AFWERX webinar last week (my first one) and was honestly surprised by how much airtime the new authority got. AFWERX is DoD-side, but the rule applies cross-agency: HHS, DOE, NSF, NASA, & DoD all qualify. Most folks analyzing it are focused on Phase II winners. The more useful question for early-stage founders: what does this mean if you're at Phase I, or thinking about SBIR for the first time? Here's a representative stack at NSF: Phase I ($305K) → Phase II (~$1.25M) → Strategic Breakthrough Award (up to $30M with matched capital). SBIR does evaluate both technical merit and commercial potential, but the new authority pushes harder on outside-capital validation and customer intent than any prior SBIR vehicle. The math compounds for early-stage founders. At seed, $305K saves ~2-6 points of cap table depending on round size. Stack Phase II at Series A and a Strategic Breakthrough at Series B, and the cumulative savings can run into double-digit points by exit. My take: set up Phase I now, alongside (or before) your next venture round, so you have the $30M option later.
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Maddi Holman
Daring Ventures • 10K followers
What is a "buyer-builder"? It's the founder archetype we back at Daring Ventures. Buyer-builders have lived experience and domain expertise on the industries they are building in. They've felt the friction and know which problems to address and who to build for. They don't need to do customer discovery because they've experienced it first-hand. Outsiders spend years and millions figuring out what buyer-builders already know. We started The Builders Series to profile the ones doing it right. This edition: Ara Mahdessian and Vahe Kuzoyan of ServiceTitan. Ara and Vahe did not need to be told that contractors were underserved. They grew up watching it. Their fathers, competent skilled operators, losing hours every week to paper invoices, missed calls, and work that software should have absorbed years earlier. Full piece on Forward This 👇
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Ivan Nikkhoo
Navigate Ventures • 30K followers
"My favorite CEO comes in, and the first ten minutes of the meeting is actually psychotherapy." We are excited to welcome Paul Martino, Managing Partner at Bullpen Capital, for Episode 2 of Charting the Course. A nine-time founder and veteran investor, Paul brings a unique perspective on the "post-seed" gap—backing founders who build in categories and geographies that others often ignore. To Paul, being misunderstood isn't an obstacle; it's often an early signal of opportunity. Full episode drops this Friday - follow to be notified. #ChartingTheCourse #VC #Startups
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Ryan Sommerville
Criticality • 11K followers
Thrilled to share the launch of Criticality, a $65M fund built to back founders solving hard, high-leverage problems at the intersection of technical complexity and real-world urgency. Criticality builds on the foundation we’ve laid at Antler - applying our conviction-driven approach to companies at Seed & Series A. The fund is sector-flexible but applies a deep tech lens to each opportunity, targeting non-obvious, high-leverage problems from the earliest stages of company formation. Grateful to the New Mexico State Investment Council for their support in anchoring Criticality. More to come soon from Cash Allred & I.
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Kal Amin
7K followers
I’m thrilled to officially announce our $3M seed investment in Propel People, a company we built inside the 1848 Ventures studio to tackle one of the biggest challenges facing the #construction industry today: the skilled #labor shortage. For small and medium-sized contractors, hiring isn't just a challenge. It's the number one threat to their growth, profitability, and safety. With 94% of contractors struggling to find qualified workers, it’s clear that traditional hiring methods aren't built for the trades. That’s why we built Propel People. It’s a mobile-first, AI-powered hiring platform designed for how construction actually works: in the field. By leveraging smart candidate ranking, instant #SMS-based screening, and a fully #bilingual interface, Propel helps contractors build great crews faster and more efficiently. I’m also thrilled to formally announce that industry veteran Dexter Bachelder is at the helm as CEO. Having worked with Dexter and the team over the last few months, we've already seen the impact of his leadership. His 25 years of experience scaling construction tech companies will be instrumental as Propel People enters this initial stage of growth. This investment reinforces our core thesis at 1848 Ventures: building AI-native companies that solve fundamental pain points for the #SMBs that form the backbone of our economy. A huge congratulations to Dexter and the entire Propel People team on this milestone. We are incredibly proud to partner with you to support the people who build our world. Read the full announcement below. #constructiontech #venturecapital #seedfunding #ai #skilledtrades #smb
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JT Benton
9point8 Collective • 8K followers
Here's a transition we see go sideways all the time: successful services business. Revenue, team, domain expertise. The next step feels obvious -- start building ventures on that foundation. In theory, elegant. In practice, one of the hardest transitions in the studio world. The core problem is that costs and benefits land in the same place. The services team builds client work (pays bills now) and internal ventures (might pay in three years). When an outside investor looks at this, the question is immediate: how do I know the best people are on my ventures and not client projects? That's not a trust problem. It's an incentive alignment problem. 📉 We've seen the same diagnosis play out repeatedly. Venture builders and service providers share the same entity, the same P&L, the same team allocation. Ventures always lose this configuration because revenue-generating work always wins the resource fight. Cleanest solution: distinct entities, distinct teams, distinct reporting. Services business funds operations. Studio entity houses ventures. Shared thesis, separate P&L. If full separation isn't possible yet, raise per venture through SPVs. Build proof points one at a time. 🎯 Here's the takeaway -- the earn-to-own path is valid. But the operators who succeed plan for structural separation from day one. They don't assume services and studio can coexist in one body indefinitely. The ones who wait to separate usually never do. ⚡
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Andrew Whitman
10K followers
Another missive from Chuck Cotter and Daniel Faierman. Thanks guys for continuing to help to ecosystem. If you've not seen their posts, peek at https://lnkd.in/gPiu9Z4z. Topics include: · CPG Co-Manufacturing Contracts · Early Stage VC Terms to Rarely Accept · More Dividends (and Dividend Recaps?) · 5 Raises, 5 Takeaways · A Founder's Guide to Secondaries · Standing Out Pre-Traction · The State of VC · Corporate Governance 101 · Anti-Dilution Provisions · Primer on QSBS · 4 Fund Raising DON'Ts · Liquidation Preferences · Understanding SAFEs · Understanding Convertible Notes · Understanding Prorata Rights · Founders & Athletes · Employee Stock Options Demystified · The Art of Start-Up Valuation · What Is A Term Sheet Anyway? Check it out ...
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Jeff Perry
16K followers
Seth Levine nailed it! The concentration problem isn't just a GP pain point... it's choking innovation. When capital pools around the same 20 funds, emerging managers and founders get shut out. Love that he's using his platform to call this out. Foundry has backed 50+ emerging managers. That's the diversification the ecosystem needs. This is exactly why Carta exists — making capital allocation visible and accessible. Capital Evolution hits at exactly the right moment. Thanks for having us Daniel Dart. Team Carta loves the community of FUTURE TITANS you have built 🚀
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Earnest Sweat
Stresswood • 17K followers
Two weeks ago on Swimming with Allocators, we sat down with David Clark, CIO at VenCap, to talk about what decades of venture data can teach allocators. One takeaway that stood out: discounts don’t matter as much as people think in venture secondaries. Because venture is such a power-law asset class, outcomes are driven by exposure to a few massive winners. Whether a stake is bought at a small discount, or even a premium, often matters far less than the quality of the underlying company and its upside. Great conversation on venture returns, manager selection, and the nuances of how allocators should think about secondary investments. 👇 Link in the comments.
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Daniel Dart
Rock Yard Ventures • 10K followers
🚨NEW EPISODE: Recorded live at FUTURE TITANS 2026 - Jeff Perry of Carta sat down with the iconic Seth Levine, co-founder of Foundry. Seth has been in venture for 25 years, built Foundry from scratch as an emerging manager himself, and has backed about 50 emerging manager funds through his fund of funds. He has genuinely seen every side of this table. They went deep on building Foundry, why VCs are in the influence business, not the decision business, and why the concentration problem in venture is not only bad for LPs, but also for the innovation ecosystem overall. And why Seth's new book, Capital Evolution, is so important for the future of America. 🎧 Links to listen... Apple: https://lnkd.in/ehQUQ2EM Spotify: https://lnkd.in/eU4FExpg
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