Sam Bobley

Andi Pitt, Managing Partner in ego death capital shares how issuing a token as an early-stage company works against you, rather than for you, in the long-term strategy of company growth. I completely agree, as well as how the vast majority of tokens issued have served only as early-exit liquidity for early investors. Have a listen:

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Tired: investing in bulge-bracket, multi-stage $1B+ firms for early stage exposure. Wired: investing in a large basket of sub $100M funds across a 25 year, multi-vintage time horizon. Take it to the bank. Savy LPs are all saying the same thing and are aiming to go smaller, more frequently. Even venture managers aren’t immune from a version of the power law - one or two outlier fund cycles can make up for all the other mediocre vintages. Risk is diversified away by being consistent in time horizon and commitment frequency/size. I, for one, like the way this is going (obviously).

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I enjoyed going on Nick Telson-Sillett’s podcast, Pitch Deck by Forward Pursuit. Nick is a serial founder and investor (founded and exited DesignMyNight) so knows both sides of the table which always makes for an enriching chat. Some things we discussed: - The perceived power dynamic between VCs and founders can hinder productive conversations. - A compelling product demo can significantly influence investor interest. - Founders must focus on solving real customer problems to succeed. - Hiring standards are crucial for building a successful startup team. - Behavioural roadblocks can prevent the adoption of new solutions. - Validation from potential customers is key for pre-revenue startups. - The early-stage funding landscape has become more efficient and selective. - Pace of execution is a critical factor in attracting investment.

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Great time on the Embracing Erosion podcast w/Devon O'Rourke! We talked about: 🚀 How to scale a company from concept to 9-figure exit 🔄 How to break away from the traditional consulting model and apply product approaches ⏩ Why it’s important to iterate quickly and often with messaging 💸📈What signals are important to pay attention to when investing in startups and much more!

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When I first read Jevgenijs Kazanins's very excellent fintech take on why Cash App Pay could be the next major driver of Block’s growth, I was floored by his initially compelling case that if Cash App can incentivize more payments payments volume to go through Cash App Pay, they can drive massive gross profit uplift, because Cash App Pay’s take rate is substantially higher than Cash Card’s take rate on purchase volume (2-3x). But if it were true, why hasn’t Cash App taken advantage? Whereas Jevgenijs is more optimistic about the ~$2.5bn in GPV that Cash App Pay has generated in its first ~2.5 years of existence, I find it downright embarrassing. That’s less than 1% of Square’s GPV after two years in the wild? And that’s despite it being essentially pre-installed on every terminal with no change in hardware required. I started to have a sinking feeling that maybe something was missing in the calculus. And as I dove deeper, it became clear that the “magic” take rate uptick we thought we’d found was more of a magic trick, relying on some deception. The seeming increase in take rate comes about like this. Normally, when a Cash App user makes a purchase, Cash App acts as the Issuer which means there are several intermediaries between what the merchant is charged and what Block earns on the transaction, meaning its ultimate take rate is relatively low. But in the case of Cash App Pay, there’s potentially a few magic tricks at work. The first is that in this case, Block is facilitating the Square merchant’s acquiring POS AND it’s issuing the Cash App user’s debit card, thereby cutting the intermediaries down in the typical payments flow and seemingly increasing Cash App take rates by 35-50% (instead of just interchange, you’re now getting interchange and markup). But then gets even better with the second trick, because if you’re both the acquirer and the issuer, *you don’t even need the payment network at all*. You can simply move money by book transfer between your merchant’s bank account and your user’s bank account in a perfectly closed loop payment network. Suddenly, Cash App Pay has a magical 2.9% take rate with no money movement costs at all. The problem with these magic tricks, like the ones in life, is that they are actually using some deception to hide what’s truly happening. Let’s play it out. In the status quo, without Cash App Pay, Square would earn ~1.85% in acquirer markup and Cash App would earn 0.90% in interchange for a total of 2.75% in take rate. In the Cash App Pay case, Square and Cash App would split the 2.90% Merchant Discount rate they artfully charged without having any money movement. So instead of the 2-3x markup, the uptick is more like +15bps (+5%). So maybe there isn’t a massive take rate arbitrage, but Block should still be focusing on its closed loop payment network because it represents huge opportunity for other reasons. Read the full post at https://lnkd.in/d93nkn29.

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Should you raise VC money❓ A question for the ages, answered by Dylan Collins on the pod this week. No one is better placed to answer this than the man who sold three companies and is now an active investor. 💡 Dylan breaks down: - Why VC money isn’t for everyone - The hidden costs of taking investment - And how to know if you’re truly ready to scale 🚀 Listen or watch now YouTube: https://bit.ly/3COsRU1 Spotify: https://spoti.fi/4fPu6Rv Apple: https://apple.co/4gaVuJo

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Crunchbase charted smaller VC funds that successfully raised capital this year. Joanna Glasner, A few callouts: 🏁"Smaller" funds (sub $500 million!) have reached the lowest raised tally in years: totaling $13.7 billion.. For context and as charted: $40 billion was raised in 2022. 🏁Larger round sizes are getting larger, i.e. OpenAI - clearly favoring funds with deeper pockets. However: smaller funds are driving the #alpha, are able to put smaller sums to work in transformational companies, and deliver returns without requiring #unicorn exits. 🏁History has shown that funds that are raised in sluggish environments tend to outperform. Accel and Andreessen Horowitz #VentureCapital #Fundraising

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Regulatory hurdles can make or break early-stage startups, but navigating them can also unlock huge opportunities. I recently sat down with Bradley Tusk, Co-Founder and Managing Partner at Tusk Venture Partners, to discuss how he and his team help companies overcome complex regulatory challenges. From backing startups like FanDuel, Lemonade, and Coinbase, to his experience as a political strategist and campaign manager, Bradley brings a unique perspective to the venture world. We explore how regulatory environments impact sectors like crypto, AI, and the gig economy—and what it takes to succeed. Catch Episode 455 of The Full Ratchet for this insightful conversation! Link to the full episode is in the comment section below.

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🚀 AlleyCorp Closes $250M Fund to Fuel Tech Innovation in NYC and Beyond🗽 🌟 Founded by NYC internet entrepreneur Kevin Ryan, AlleyCorp incubates and invests in transformative companies across diverse verticals including Diversified Technology, Healthcare, Robotics, and Impact. 💡💰 🤝 The fund, backed by a select group of LPs, supports AlleyCorp's mission to originate ideas, hire teams, provide initial funding, and maintain integral leadership throughout the company’s lifecycle. 🌱🔍 💼 With about 20–30 new investments and 5–8 incubations per year, AlleyCorp has a track record of nurturing early-stage tech pioneers. 📈🌐 🦄 Notable investments include MongoDB (NASDAQ: MDB), Business Insider, Gilt Groupe, Zola, and Nomad Health, shaping the landscape of tech innovation in NYC. 🌆🌟 🔬 AlleyCorp also announces the incubation of Radical AI, pioneering AI-driven materials design, and Conduce Health, revolutionizing access to personalized healthcare specialists. 💻🏥 ✅ Looking to raise capital for your #fund and increase the international pool of your LP #investors?   🤝 Need warm #LP introductions?   📝 Selling #secondaries to increase liquidity?   🧐 Looking for co-investments?   ▶ G+QUANT's link for inquiries and fund decks: https://lnkd.in/gjC_EuTE #VentureCapital #TechInnovation #NYCTech #StartupInvestment #Incubation #AlleyCorp #ImpactInvesting #HealthTech #AI #Robotics #DiversifiedTechnology #InvestmentStrategy

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Another Private Equity Myth BUSTED: The Myth: All that matters is closing the deal. THE TRUTH: Winning the deal is only the beginning. I once knew a couple who was so obsessed with just getting married, they viewed it as the finish line..... was a hard wake up call! Incredible PE operators don’t just stop at acquisition—they obsess over the post-close plan. Before the ink is dry, they already know: What operational improvements they’ll tackle first. How they’ll grow EBITDA over the next 18 months. Which new markets or strategies will drive future value. Novice buyers think their work is done when the deal closes. Great buyers know that’s when the real work begins. Execution post-acquisition is what separates the good from the great. That’s how you create lasting success in private equity.

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As the year winds down, founders looking to raise debt capital in 2025 should focus now on making their companies as attractive as possible to potential lenders. The work you put in today can set you up for success and ensure you hit the ground running in January. Here are a few steps to prepare: ✔ 𝗚𝗲𝘁 𝘆𝗼𝘂𝗿 𝗳𝗶𝗻𝗮𝗻𝗰𝗶𝗮𝗹𝘀 𝗶𝗻 𝗼𝗿𝗱𝗲𝗿. Make sure your financial records are accurate and up-to-date. Be ready to share key metrics and demonstrate a clear understanding of your cash flow and runway. ✔ 𝗦𝗵𝗼𝘄 𝗲𝘃𝗶𝗱𝗲𝗻𝗰𝗲 𝗼𝗳 𝘁𝗿𝗮𝗰𝘁𝗶𝗼𝗻. Highlight meaningful milestones like revenue growth, customer acquisition, or product development. Lenders are drawn to companies with proven momentum. ✔ 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝗰𝗼𝗺𝗽𝗲𝗹𝗹𝗶𝗻𝗴 𝗽𝗶𝘁𝗰𝗵. Beyond a solid business plan, refine your ability to communicate your vision, market opportunity, and path to sustainable growth. ✔ 𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝗮𝗹 𝗲𝗳𝗳𝗶𝗰𝗶𝗲𝗻𝗰𝘆. Demonstrate that you’re using resources wisely and running a lean operation. Efficiency signals discipline and readiness for growth. ✔ 𝗙𝗶𝗻𝗱 𝘁𝗵𝗲 𝗿𝗶𝗴𝗵𝘁 𝗳𝗶𝗻𝗮𝗻𝗰𝗶𝗻𝗴 𝗽𝗮𝗿𝘁𝗻𝗲𝗿𝘀. Look for lenders who offer more than capital—mentoring, support, and networks can be just as valuable in the long run. I’ve always believed that while success often involves a bit of luck, you can take the right steps to make your own luck. This is an important time of year—make the most of it. And as always, if you’re a late- or growth-stage company exploring debt financing, feel free to reach out—I’d be happy to connect.

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Is Bolt’s new $450M raise bold or reckless? I just saw this news (https://lnkd.in/eq9PxW8U)- Ryan Breslow is back at the helm, driving Bolt.com to a $14 billion valuation, not long after a $300 million stock buyback valuation that crushed the spirits of their employees who exercised their options at their last valuation. I'm all for founder-led companies with a little dash of crazy, but I don't like the smell of this new raise at all This dramatic turnaround, fueled by international investors, raises more questions than confidence. Breslow’s move feels more like an Adam Neumann-inspired hype play than a true growth strategy. The focus is on challenging Stripe and fueling FOMO, not on sustainable fundamentals. For founders and investors, this is a reminder: don’t let flashy narratives blind you to the reality of valuations. I’m all for supporting founder-led companies—it takes a little crazy to be a founder at this scale—but this one might be a step too far IMO. What’s your take on this announcement? All hype or the next Stripe killer?

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𝐍𝐨𝐭 𝐚𝐥𝐥 𝐕𝐂 𝐟𝐢𝐫𝐦𝐬 𝐚𝐫𝐞 𝐜𝐫𝐞𝐚𝐭𝐞𝐝 𝐞𝐪𝐮𝐚𝐥... 𝐓𝐡𝐞𝐫𝐞 𝐚𝐫𝐞 𝟔 𝐝𝐢𝐟𝐟𝐞𝐫𝐞𝐧𝐭 𝐭𝐲𝐩𝐞𝐬 𝐨𝐟 𝐟𝐢𝐫𝐦𝐬 𝐲𝐨𝐮 𝐬𝐡𝐨𝐮𝐥𝐝 𝐤𝐧𝐨𝐰. When looking to break into VC or move to a new role within VC, it’s incredibly important to understand the nuances of different types of VC firms. The type of firm dictates your role and affects what your day-to-day looks like. It’s also incredibly important for founders to understand the different types of firms as it will affect how, when and why they support you. 𝐓𝐡𝐞𝐫𝐞 𝐚𝐫𝐞 𝟔 𝐦𝐚𝐢𝐧 𝐭𝐲𝐩𝐞𝐬 𝐨𝐟 𝐕𝐂 𝐟𝐢𝐫𝐦𝐬: 1️⃣ Micro VC 2️⃣ Institutional VC 3️⃣ Corporate VC 4️⃣ Government VC 5️⃣ Family Office 6️⃣ Angel Syndicate The quick TLDR is that all these VC firms are very different. 𝐓𝐡𝐞 𝐕𝐂 𝐟𝐢𝐫𝐦𝐬 𝐯𝐚𝐫𝐲 𝐛𝐲 𝐋𝐢𝐦𝐢𝐭𝐞𝐝 𝐏𝐚𝐫𝐭𝐧𝐞𝐫 𝐛𝐚𝐬𝐞, 𝐢𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭 𝐬𝐭𝐚𝐠𝐞, 𝐜𝐡𝐞𝐜𝐤 𝐬𝐢𝐳𝐞𝐬, 𝐨𝐰𝐧𝐞𝐫𝐬𝐡𝐢𝐩 𝐭𝐚𝐫𝐠𝐞𝐭𝐬, 𝐝𝐢𝐥𝐢𝐠𝐞𝐧𝐜𝐞 𝐭𝐢𝐦𝐞𝐥𝐢𝐧𝐞, 𝐢𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭 𝐨𝐛𝐣𝐞𝐜𝐭𝐢𝐯𝐞𝐬, 𝐜𝐨𝐧𝐭𝐫𝐨𝐥 𝐥𝐞𝐯𝐞𝐥𝐬, 𝐫𝐢𝐬𝐤 𝐚𝐩𝐩𝐞𝐭𝐢𝐭𝐞 + 𝐦𝐨𝐫𝐞. For VCs, this is helpful for many reasons. It can help you choose the right role for you. It can help you build out syndicates for your portfolio companies. It can help you with intentional networking. Overall, it will make you a more strategic investor. For founders, this is critical information to know as you think about who will sit on your cap table. Choosing the right partners that fit your business goals and values will be a key part of your success. #venturecapital #startup #founder #recruiting #fundraising

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Let’s get aspiring VCs noticed 🌟 Investors & platform folks! I post a list of weekly VC job openings every Wednesday. My mission is to open as many doors as possible for other people so that weekly post is meant to help folks break into the black box that is VC. Another way I like to push that mission forward is by having aspiring VCs flag themselves on my posts for VCs who are hiring to see. It’s worked on other platforms. Let’s try it on LinkedIn! 👤 Name 📍 Location 💼 Desired role 💎 Investor or platform* 📊 Stage focus 🔍 Industry focus *Investor refers to those who source new companies for investment & platform refers to those who support portfolio companies post-investment. For those looking for help breaking into VC, check out my blog: https://lnkd.in/eNXQ7_uS 25+ deep-dives on all things VC recruiting + the opportunity to speak with me live. #venturecapital #startup #recruiting #hiring

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Let’s get aspiring VCs noticed 🌟 Investors & platform folks! I post a list of weekly VC job openings every Wednesday. My mission is to open as many doors as possible for other people so that weekly post is meant to help folks break into the black box that is VC. Another way I like to push that mission forward is by having aspiring VCs flag themselves on my posts for VCs who are hiring to see. It’s worked on other platforms. Let’s try it on LinkedIn! 👤 Name 📍 Location 💼 Desired role 💎 Investor or platform* 📊 Stage focus 🔍 Industry focus *Investor refers to those who source new companies for investment & platform refers to those who support portfolio companies post-investment. Learn the 8-steps of a VC interview process here: https://lnkd.in/gri__2vu #venturecapital #startup #recruiting #hiring

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Ada Ventures wants to help VC break free of pattern-matching by Martin SFP Bryant, Founder of PreSeed Now 👇 Why it matters 👇 Ada Ventures stands out by prioritizing inclusivity over traditional VC “pattern matching.” Co-founded by Francesca (Check) Warner, the fund backs non-traditional, high-potential founders at pre-seed, tackling tough societal challenges in health, climate, and economic empowerment. Warner argues that “pattern breakers,” like Ada Lovelace, drive innovation by thinking beyond mainstream assumptions. With a portfolio of 40+ companies and backing from top funds, Ada Ventures has shown that inclusivity isn’t just ethical—it’s profitable. Warner hopes to see other funds adopt similar inclusive practices to broaden VC’s scope and impact in 2025. Read the full article or report on EUVC Insights! 🔽 https://buff.ly/4hZrTo3 #venturecapital #startupfunding #Europe #EUVCInsights

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