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Brooklyn, New York, United States
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16K followers
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Charlie is a highly sought after coach to…
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Articles by Charlie
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What could Siri do for you--if Apple ever got it right?
What could Siri do for you--if Apple ever got it right?
This article also appears, as does all of my longer form writing, here--which is where you're better off subscribing to…
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The Five "Ups" of Getting Early Stage VC Deal FlowMay 2, 2025
The Five "Ups" of Getting Early Stage VC Deal Flow
This post also appears in the long form newsletter/blog that I've been writing since February of 2004. I don't always…
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1 Comment -
VCs Don't Owe You a Response or a Follow UpJan 28, 2025
VCs Don't Owe You a Response or a Follow Up
Note: I normally write over here but a few folks I know that have newsletters have mentioned that LinkedIn posting…
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12 Comments -
Moving Fast, Breaking Things, and the Support of DisruptionJun 1, 2020
Moving Fast, Breaking Things, and the Support of Disruption
I wrote this in my newsletter this morning. If you're not willing to ask yourself difficult questions, to be asked…
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7 Comments -
Some Thoughts on WeWork and Investing in Late StageSep 6, 2019
Some Thoughts on WeWork and Investing in Late Stage
I got asked by a reporter yesterday what I thought about WeWork’s IPO situation and I’ll summarize what I said here:…
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The Achilles Heel of Startup EcosystemsMar 18, 2019
The Achilles Heel of Startup Ecosystems
Across the world, various economic development organizations, government agencies, and non-profits are putting in…
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Being in the MinorityDec 12, 2016
Being in the Minority
Over the last couple of weeks, I've been to a couple of tech events that were sparsely populated by straight white men.…
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Activity
16K followers
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Charlie O'Donnell shared thisI was Edward Woodford's first outside investor back in 2015. He spent two years getting that company licensed, got to the start line, and realized they were about 10 years too early. How'd it turn out? "We weren't a VC return...we made a little bit of money for everybody and that was okay." What happened? In a regulated market you hyper-fixate on the license. "Get licensed, I will be successful." Then the license becomes the whole business and regulation turned out to be necessary, not sufficient. That's the whole reason zerohash exists, so other people don't burn two years just getting to the start line. Same goes for anyone spinning a compound out of a lab or building a medical device. You can't sell it without FDA approval. Once you have it, you still need GTM, a team, and dollars for marketing. The full episode of my conversation with Edward is up on the nextNYC podcast today! 🎧 Listen here: Apple Podcasts: https://lnkd.in/e8nAj5SH Spotify: https://lnkd.in/ev3yE4Zj iHeart Radio: https://lnkd.in/eh6VzB7w YouTube: https://lnkd.in/eCJ2yurk
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Charlie O'Donnell shared thisWhat do you think when you hear that I've kayaked in the Hudson and East Rivers in New York City? If you've done it, you know what an amazing way to experience the city it is. If you haven't, you might think, "Ew." So whether I have anyone to *thank* for it probably depends on your perspective on whether it's the gift that I think it is. Kayaking is something I've been doing in New York's waterways for over 23 years--longer than I've been bike commuting, actually. This post is about thanking the people who got me into it. In 2003, I showed up to the Downtown Boathouse and attempted to get on one of their trips. When I didn't get in via a lottery, I started volunteering, and Graeme Birchall ((https://lnkd.in/ei7H3a4k) was the first person I ever met there. Years later, I'd help tim gamble with a test program in Brooklyn's Dumbo Cove, even before Brooklyn Bridge Park was even a thing. When the Park was ready to open Pier 1, they reached back out to Tim, who replied, "I'm moving to Fiji, talk to these guys..." Good thing he cc'd Tom Potter and others like Bill Orme and Rob Buchanan on that note, because as much as I was excited to work on a program in Brooklyn, I had no idea how to build a community organization. Today, the Brooklyn Bridge Park Boathouse puts thousands on the water every year thanks to over 200 active volunteers. I can't tag them all here, but if you want to join them you should come to our upcoming offseason recruiting session on November 14th. We'll share how our organization works and how you can get involved both on the water and off. We have lots to do before we get back on the water in May! --> https://lnkd.in/epih8VRF
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Charlie O'Donnell shared thisVivek Sharma ran Movable Ink for sixteen years, sold a majority stake to a private equity firm, and then handed the CEO job to the guy he’d hired as his first manager. So I asked him the question founders ask me constantly: what does a productive investor relationship actually look like? Everybody has heard the warnings. “You’re going to lose control.” “They’ll be in your ear every week.” “Don’t send them too much, they’ll be all up in your business.” His answer was the opposite. Send them everything. The raw data first, then your lens on it. They’re going to find out the truth two months after the check lands anyway, so there’s no upside to a glaring surprise at the first board meeting. Then he talked about STG, the PE firm that bought the company. They walked in and said: here’s what your customers told us, here’s what you do well, here’s what you could fix, here’s what we think the financial profile could be. Now tell us where we’re wrong. Three months later, the ask hadn’t moved an inch. And they went back to a CEO of a company they’d previously acquired and asked for feedback on themselves as a firm. Investors are very good at giving feedback, yet almost none of them ask for it. I wrote a whole book about getting the money (Founder Unfriendly: What Investors Won't Tell You About Getting Funded: https://lnkd.in/eA_5vcFU). Vivek’s point is about what happens after, and it turns out to be the same thing: the relationships that work are the ones where nobody is managing the other side’s information. The full episode with Vivek is out today on the nextNYC podcast! 🎧 Listen here: Apple Podcasts: https://lnkd.in/eXnfieeq Spotify: https://lnkd.in/erM2Jr_z YouTube: https://lnkd.in/e_FDkEuG iHeartRadio: https://lnkd.in/gHTYKn-YFounder Unfriendly: What Investors Won't Tell You About Getting FundedFounder Unfriendly: What Investors Won't Tell You About Getting Funded
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Charlie O'Donnell shared thisAudrey Gelman told me the male investors in The Wing were the best and most loyal ones when things went bad in 2020. "Take from that what you will," she said. That's episode two of the nextNYC podcast, out today! I wrote one check into the seed round in 2015, when the deck still said "Refresh Club" and the Mets were good. By 2020 she'd gone from the cover of Inc. to a new baby, to raising $50 million to buy out WeWork's stake, to every club shutting down and people on the internet wanting to see her go down. Four or five months, start to finish. So I didn't ask how you avoid that. I asked what helps once you're in it. Her answer was older women, including one who emailed her, "My obituary has been written 10 times in my career. I would bet on you." Also in there: why fundraising is horrible for everyone, whether being the face of a brand is worth it, and the call she was scared to make to the investors who lost money. She made it anyway, and a number of them put money into The Six Bells. 🎧 Listen here: Apple Podcasts: https://lnkd.in/emTYN-BN Spotify: https://lnkd.in/eCzr9g_N iHeart Radio: https://lnkd.in/e3FXx_uZ YouTube: https://lnkd.in/ej8UBbV2nextNYC: Startups, Venture Capital, Made in New York CitynextNYC: Startups, Venture Capital, Made in New York City
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Charlie O'Donnell shared thisThank you Kara Swisher. About 16 years ago, I invited my favorite tech journalist, Kara Swisher, to come speak at Fordham University about the book she had written on AOL. This was well before NYC was the tech hub it was today--and startups weren't really on the radars of most University students at the time, so the attendance was kind of embarrassing. (We didn't have Facebook to get the message out to everyone.) Kara couldn't be more gracious about it, especially given that she hiked up to the Bronx to get there. Her reaction to the small crowd made running tech events less intimidating for me, as well as taking big swings with my asks for guests. Well, things have come full circle as I'm now the guest speaker in that very same auditorium talking about AI, startups and my book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded. (https://luma.com/xvi7hm30) in front of a group of Fordham Gabelli School of Business students.
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Charlie O'Donnell shared this16 years ago I sat across a table from two engineers who worked at Wireless Generation in Dumbo, which might have been the biggest tech company in Brooklyn at the time, well before anyone thought Brooklyn was a place you built tech. I was at First Round. I had no technical knowledge whatsoever, so they seemed like they knew what they were talking about. That was Alexis L. and Olivier Pomel. The company was Datadog. Today the nextNYC podcast is officially live, and my conversation with Alexis is the first episode. Would anyone in New York fund an infrastructure company in 2010? No. Alexis will tell you exactly what the pitch meetings sounded like: "You're not ad tech, you're not mobile, you're not marketing. I don't know what you guys are doing here." So they stopped trying to convince investors and went and got customers. It took until December 2014, four years after they founded the company, before Alexis felt like there might be something there. Four years of signing customers, small and big, with a lot of regularity, and still thinking "maybe this month is the peak and everything's downhill from here." That's the co-founder of the company that put New York on a bigger map and raised the bar for everyone building here. He's still there, and he doesn't have to be. He said something near the top of the interview that is basically the mission statement for this show: the startup world has a lot of polished stories and not a lot of what truly happened. That's the bar. One new episode every day this week: Audrey Gelman of The Six Bells (formerly The Wing, where I was a seed investor), Vivek Sharma of Movable Ink, Zuben Mathews of Brigit, and Edward Woodford of zerohash. nextNYC: Startups, Venture Capital, Made in New York City. Listen here 👇 Apple Podcasts: https://lnkd.in/e8nAj5SH Spotify: https://lnkd.in/gGrsA7WJ YouTube: https://lnkd.in/gSP5aV8C iHeartRadio: https://lnkd.in/gHTYKn-
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Charlie O'Donnell shared thisThank you, Dennis Crowley. You knocked over the first domino in a series of events that led to me getting back into venture after my own failed startup, and you've always reminded people that tech's goal should be to bring us together in the real world. For those of you younger folks in tech who've seen the news about Foursquare's sale and are scratching your head as to why people are so nostalgic about this company, you have to understand what it meant to New York City tech at the time. In late 2008, the financial crisis had put venture funding in New York City into a deep freeze. The New York startup scene was seen as being driven by Wall Street wealth, and if that dried up, New York and the entrepreneurs in it were fully expected to pick up their marbles and go home (the way they did when the dot-com era burst). There wasn't a previous generation of tech startups to go back to working at large tech companies, the way it was in the Bay Area. Instead, quite the opposite happened. The hottest startup funding in 2009 didn't come out of the Valley, and it didn't come out of Boston. It blew up in the late summer of 2009 in New York City. Just before that, a string of blog posts between me (https://lnkd.in/e-AFURZQ), Fred Wilson (https://lnkd.in/e45HYBGR), and M.G. Siegler (https://lnkd.in/e28uttJH) at TechCrunch kicked off a hyper-competitive month for funding the next big thing in social networking. As Eric Friedman put it (https://lnkd.in/e8MBEJ4m), Foursquare "had captured the zeitgeist of New York tech" and "became a magnet for talent." Moreover, it was the backbone of a scene that was fueled by meetup hopping and IRL gatherings. Nostalgia for Foursquare is less of a story about missed equity upside than a story about a generation of New York tech kids, before we all had kids, trying to build a friendlier, less lonely internet. Plus, true New Yorkers always have a bit of place nostalgia for the spots that used to be. I don't miss the digital crown of Mayorship of Coffee Shop and my hard fought battle with Fred Wilson for it nearly as much as I miss the actual place and actually running into him and nearly everyone else from the tech community there. You can hear Dennis talk about bringing people together in the real world at dev/ai/nyc this Wednesday: https://luma.com/sjnwdzsw
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Charlie O'Donnell shared thisAll of the amazing conversations I've been having with founders and investors through nextNYC now have a home and an easier way to get them as we publish. This Monday, we'll be posting our first episodes of the nextNYC podcast. Our opening week is epic: Monday Alexis L., co-founder & CTO, Datadog He co-founded one of the most valuable tech companies ever built in New York. Here's what the early years looked like from the inside. Tuesday Audrey Gelman, founder of The Six Bells, former founder & CEO of The Wing Raising money as the face of a brand, the backlash, and what she'd tell investors now. Wednesday Vivek Sharma, founder & CEO, Movable Ink Fifteen years, 700+ of the world's biggest brands as customers, and no shortcut in sight. The long game, from someone still playing it. Thursday Zuben Mathews, co-founder & CEO, Brigit He turned down my first term sheet, let me on the cap table anyway, and sold the company for $460 million. We talk about all three. Friday Edward Woodford, co-founder & CEO, zerohash The crypto infrastructure company behind the apps you've actually used. Building the boring, regulated plumbing in a very unboring industry. Apple Podcasts: https://lnkd.in/gnmr2MSm Spotify: https://lnkd.in/gGrsA7WJ YouTube: https://lnkd.in/gSP5aV8C iHeartRadio: https://lnkd.in/gHTYKn-Y RSS: https://lnkd.in/gd6gN973
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Charlie O'Donnell shared thisIn this month’s Qapita x nextNYC webinar, I asked Chris Hoffmann, ECA why equity feels great on day one and then stops mattering so much. Chris compared it to Christmas morning. It’s exciting at the grant, exciting again at the cliff, and then it starts to fade around 50% vested. He says that’s when you should be talking to people about a refresh, before they start taking recruiter calls. Thanks to Qapita for partnering with nextNYC on this series! #ESOP #EmployeeEquity #StartupEquity #Retention #Founders #nextNYC #Qapita
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Charlie O'Donnell reacted on thisCharlie O'Donnell reacted on thisSeven years ago Chapter One was a blank page and a small first fund. Today we’re announcing Fund III. We name every fund like a book. This one is a question. What if it all works?Introducing Chapter One Fund III: What If It All Works?Introducing Chapter One Fund III: What If It All Works?Jeff Morris Jr.
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Charlie O'Donnell liked thisCharlie O'Donnell liked thisLooking for a volunteer opportunity in NYC?- come to our open house on November 14th (St. Ann's Warehouse - 45 Water St, Brooklyn NY) @ 10am Sign up here: https://lnkd.in/eBq_sa5z
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Charlie O'Donnell liked thisCharlie O'Donnell liked thisThis is not a career post Hey dad, I miss you so much. I wish you most of all had known what I discovered through 23andme. I am certain like thousand dollar bet certain that your first words would’ve been “far out”. I believe that we would’ve uncovered so many truths that you knew but couldn’t figure out. I wish the secrets had been revealed to you and I wish we could share them and I wish I had the learnings from that. I wish you could’ve met Heather to falsify your professed displeasure of southern women. This one I know you would have adored. I wish you had met Hazel and I wish you could’ve seen what Liberty has become. I wish you could’ve seen how cool everybody in your life continues to be. Sharon, your other kids, everybody. They just keep getting cooler. You are gone. I feel this when I think of something that I would love to tell you – that I think you would think was super cool. Your tribe is doing OK and so there’s lots of things that are super cool that I wish I could’ve shared with you. I love you. I wish we could’ve figured out how to share more love although in the totality of measurement of all of things possible, we didn’t do too bad. Tonight I could be thinking of many things, but I’m just sitting here in my car, crying a little bit and feeling my love for you. I love you, dad I’m glad you were my dad
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Charlie O'Donnell reacted on thisCharlie O'Donnell reacted on thisWe've got two great VC/PE conversations coming up, thanks to the Fordham Venture Capital Club (Graduate), Fordham Foundry, and Fordham Gabelli School of Business: Nov. 5 | Samantha Ory, co-founder of 8 Pillars Capital, shares what goes into launching a private equity firm and investing in consumer brands. Hosted @ Fordham Lincoln Center. 🔗 https://luma.com/etti7umr Nov 10. | Charlie O'Donnell, founder of Brooklyn Bridge Ventures, joins us to talk entrepreneurship, fundraising, and what it takes to build something. Hosted @ Fordham Rose Hill. 🔗 https://luma.com/xvi7hm30 Come join us!
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Peter Kellner is the founder of a deep‑tech company developing a patent‑pending, Rust‑implemented, mathematically substantiated architecture for trustworthy autonomous and semi‑autonomous systems. He previously co‑founded Endeavor Global, founded Richmond Global, and serves as a trustee and investment committee co‑chair of America Media | The Jesuit Review. He was a Fulbright Scholar to Hungary.
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Dr. Balaji Vasudevan, Ph.D.
AgriNext Conference • 37K followers
🚨 SBIR/STTR STARTUPS: Is your company ready for the next commercialization milestone? The U.S. Small Business Administration (SBA) has published updated minimum commercialization performance standards for companies receiving funding through the Small Business Innovation Research (SBIR) and Small Business Technology Transfer (STTR) programs. 📌 What founders need to know: 🔹 Who is affected? Companies that received more than 25 Phase II awards across participating agencies during the five most recently completed fiscal years, excluding the current fiscal year. 🔹 FY2027 threshold: At least 33% of total company revenue must come from sources other than Phase I and Phase II SBIR/STTR awards. 🔹 FY2028 onward: The required non-SBIR revenue share increases to 50%. 🔹 What counts? Private commercial revenue, non-SBIR government contracts and Phase III SBIR/STTR awards count toward the non-SBIR revenue share. 🔹 Why it matters: Companies that fail to meet the applicable benchmark would be ineligible to submit a new Phase I or Direct-to-Phase-II proposal to participating agencies for one year following the determination. 📅 The notice states that the standards take effect November 15, 2026, subject to publication on SBIR.gov. The notice also provides for a final benchmark following review of public comments. 💡 My takeaway for deep-tech founders: Non-dilutive funding can be an excellent catalyst for early-stage innovation, but it should be part of a broader commercialization strategy. Customer discovery, paid pilots, strategic partnerships, licensing, private investment and revenue generation need to be planned early, not after grant funding runs out. For founders, incubators, accelerators and technology commercialization teams, this is a timely reminder to connect R&D milestones with a credible path to market. 🚀 Build the technology. Validate the market. Plan for sustainable revenue. 🔗 Read the official Federal Register notice: https://lnkd.in/e8Pv9mkq #SBIR #STTR #DeepTech #Startups #TechnologyCommercialization #NonDilutiveFunding #Innovation #Entrepreneurship #VentureBuilding
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Matt Littell
2K followers
The search fund model is built on alignment. But "usually" isn’t "always." While search funds are collaborative by design, collaboration doesn’t eliminate tension. Based on experiences from both sides of the table, our latest note explores the moments when incentives between ETA CEOs and investors naturally drift apart. Why this matters: It’s Structural: These aren't "bad actor" stories; they are inherent constraints of the model. It’s Predictable: Tensions surface when timelines, personal realities, or stakes shift. It’s Navigable: Understanding these frictions upfront builds empathy, clearer expectations, and better discussions. Grateful to collaborate with Alex Hodgkin, CFA, and A.J. Wasserstein on a topic that rewards honesty and dialogue over optimism alone. Read the full paper at: https://lnkd.in/e_eskQ9V #ETA, #SearchFunds, #Searchfund, #EntrepreneurshipThroughAcquisition, #Entrepreneurship, #CorporateGovernance, #InvestorRelations, #PrivateEquity, #YaleSoM, #Kellogg, #Booth
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Tayo Olowu
Beyond Venture Limited • 11K followers
A couple of months ago, we launched the Beyond Venture Limited VC Training Program to help aspiring investors, operators, and ecosystem builders develop a practical understanding of venture capital. The response has been incredible, and as we approach the final stretch of the program, I want to encourage everyone currently enrolled to stay the course. We have just two classes remaining, with the next session taking place this Monday. Building on that foundation, all participants of that program will transition into the Beyond Venture VC Internship Program, which officially begins on June 22nd. Unlike traditional internships focused on observation, participants will work directly on venture capital activities including market research, deal sourcing, due diligence, founder support, investor relations, and fund operations. Interns will gain exposure to the full investment lifecycle while contributing to real projects and supporting real founders. All Interns will be split into rolling teams covering all areas of VC. Investment Team Due Diligence Team Portfolio Support Team Research & Intelligence Team Every Intern will work on each team for a selected period and work on actual work to gain first hand experience across board. Too many people learn venture capital from books, podcasts, and X threads. We believe the best way to learn is by doing the work. The internship is designed to bridge the gap between theory and practice, giving participants experience that translates directly into careers in venture capital, startup investing, founder support, and ecosystem development. For those currently in the VC Training Program, finish strong. For those looking at still joining please make sure you join quickly as we have two classes left, you can watch the recordings of the previous sessions and catch up. All participants get transitioned into the Internship directly. 10 days left. Register using the link below. https://lnkd.in/d5mStkJ6
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Brandon Sedloff
Juniper Square • 21K followers
Every operator thinks they’re “institutional.” But their balance sheet, GP commit, and fund structure say otherwise. Early-stage teams need guarantees. Mid-scale groups need GP co-invest relief. Mature platforms need repeatable LP capital. Until you know where you sit on that continuum, every co-GP conversation is just guessing a guess price, power & leverage. In my recent conversation with David Robertson, CEO of FrontRange Capital we unpack some of the mechanics of GP capital needs and the sources available to help.
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Chris Cunningham
15K followers
Congrats to Robert Kwiatkowski and the Discernis team on closing their $2.5M seed round. Discernis is exactly the kind of AI application we look for at C2 Ventures: replacing a highly manual, monotonous, and error-prone workflow in a large legacy industry. The platform can review more than 50,000 documents per hour, connect evidence across entire document collections, and run inside a firm’s own infrastructure without sending sensitive data to third-party AI providers. That means faster, more complete analysis while freeing attorneys to focus on the judgment and strategy they are actually trained for. A strong fit with our thesis, and great to see the team gaining traction with Am Law firms. Keep building.
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Harvrinder Athwal
XSS Capital Ltd. • 28K followers
Can fundraising teams detect a stalled process before silence becomes the strategy? The forwardable lesson is that long sales cycles need an early-warning layer, not simply more activity at the top of the funnel. The system is designed to recommend action, not merely record that progress slowed. The Long Cycle RAISE combines mandate scoring, allocation signals, trigger detection and pipeline intelligence to surface issues earlier. The Warning Layer The workflow can track investor stage, relationship activity, soft commitments, hard commitments and risks around the target process. The Waiting Problem The company is addressing a process that managers already understand and repeatedly need to solve. RAISE is raising capital and looking for investors. See company website https://raiseplatform.eu and then DM me for more info. Is faster feedback more valuable than faster outreach in institutional fundraising?
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