Sydney Rossman-Reich

One thing VC portfolio teams pick up on almost immediately: Founders who sound like they’re raising Series A, but present like they’re still at Seed. That mismatch is a silent deal-killer. Data from Carta makes the pattern clear. There’s a sharp drop-off between Seed and Series A, and each new cohort is finding it harder to make the jump. Why? Because at Series A, investors aren't evaluating your vision anymore. They're evaluating your operating system. And design is the fastest signal of that shift. Dense slides. Story-heavy narratives. Loose structure. All of it subtly communicates the same things: - Priorities aren’t locked - Reporting and decision systems aren’t clean - Execution may still be evolving Series A decks aren’t prettier Seed decks. They should visually demonstrate: – Clear focus – Clear priorities – Clear systems We've put together a detailed guide showing how a pitch deck should evolve from seed to series A with a healthcare startup case study here: https://lnkd.in/dZce6pvF What’s the one slide in your deck that still feels “Seed-stage” to you? #SeriesA #VCfundraising

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For Founders & builders: ( paraphrasing Jason Lemkin) Coding agents and customer service is solved problem, lean into untapped domains where adoption is low (e.g. finance , HR , sales etc) .46% organizations cite integration with existing system as main bottleneck for agent deployment . That’s the problem to solve for builders . If you're a enterprise buyer deploying AI in sales or finance today: agentic AI projects are at risk of cancellation in 2027 if governance, observability, and ROI clarity are not established The failure mode isn't that the technology fails. It's that the deployment isn't scoped tightly enough, the data isn't clean enough, and the success criteria aren't defined clearly enough. Pick one workflow where the data is accessible and the outcome is measurable. “ Choose a narrow problem Prove ROI Expand Rinse & Repeat #agents #AI #build #deploy #prove #ROI #niche #data #workflow

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That list of 200 contacts you're planning to tap for deal flow? You'll burn through your best ones in year one. This catches almost every new studio operator off guard. The warm introductions dry up. The "just reaching out" emails stop getting responses. The network that felt infinite suddenly has edges. **Why this matters:** Sustainable deal flow requires systems, not rolodexes. The operators who avoid this trap build sourcing infrastructure early — content that attracts, events that convene, partnerships that generate. They treat their personal network as a bridge, not a foundation. If your year-two pipeline depends entirely on your year-one relationships, you're already in trouble. The question isn't "who do I know?" It's "what system will generate opportunities I don't yet know about?"

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Pump.co is amongst YC’s fastest growing companies, ever. Their sales team is a big part of this with many reps regularly closing > $500K ARR a month (!) - only ~2 years into Pump.co launching! [This is real ARR, not the kind some AI companies are reporting these days] I sat down with their sales leader Paul Russo to dive in on how they built such an incredible GTM organization. Here are 3 cornerstones of how Pump.co gets new team members up and running fast: 1) Get them on phones asap The first days are all about keeping the setup light and getting new hires going asap. On Day 1, new reps learn the tools + fundamentals, get a company + product” bootcamp (“Pump University”), and do a trivia to lock in key concepts. Thereafter, they start calling. Many on Day 1 already. All are on the phone latest by Day 2! On top, reps (new and old) are all in the same room to learn from each other in real time (learning by osmosis). This is supplemented by group mock cold-calls and mock demos daily - even weeks into their tenure. Practice never stops at Pump.co. Here’s why this process works so well: Early, frequent reps compress the learning curve and surface the real objections you must solve far faster than slide decks ever will. 2) Coach hard, early Reps are expected to get to visible traction in < 60 days. If a new rep is behind after as little as 2 weeks, Pump.co intervenes immediately and gives them a structured improvement plan: • Name 2–3 specific gaps (e.g., opener, discovery depth, objection handling) • Daily practice: 1 mock cold‑call + 1 mock demo with feedback • Buddy shadowing in call rooms; same‑day notes and replay reviews • Tight loop: agree on one focus for the next live block; review, repeat Importantly, Pump.co always coaches to outcomes: Anchor feedback to booked meetings and moved opportunities (not theory). Plus keep corrections short and frequent so reps can try the change in the next hour (not week). 3) Have a clear promotion ladder People work harder when the promotion path is clear and written down. At Pump.co, the ladder for new BDRs looks as following: • BDR1 → BDR2: 3 straight months of 20+ qualified demos and strong team behavior. Minimum 750 dials / day. • BDR2 → SMB AE: 5 spiffs tied to $100k closed‑won (sourced / influenced), consistent 20 qualified meetings / month, plus 3 self‑sourced wins. • SMB AE → Mid‑Market AE: >$500k closed in the trailing 6 months, 5 self‑sourced deals above the SMB band, clean CRM hygiene. Typically handles ~$15k–$75k set demos; can self‑source any size. • Mid Market AE → Enterprise AE: ~$1M/year, several $100k+ wins, visible leadership. AEs still prospect: ~250 dials/day. Each candidates has regular promotion‑readiness reviews against these numbers so ambition stays productive. On top, Pump.co puts a lot of effort into making sure the system remains fair - flat orgs get political unless criteria are explicit. No wonder they built such a strong sales team.

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After scaling Rupa Health to $75M, Koby went back to zero. He sold his life, moved to Argentina, and started Sunflower. In this episode, I sat down with Koby Conrad 🌻, CEO of Sunflower 🌻(YC F25), to dissect how he built a high-growth machine in a market most VCs are too "refined" to touch: Global Addiction. We pull back the curtain on: - The Alpha of Stigma: Why "emotionally hard" markets offer the highest venture returns. - The "No-Meeting" SAFE: How Koby raised $350k before a single Zoom call, and what that means for the speed of the current YC batch. - Vibe Coding vs. Real Moats: Why your SaaS portfolio is sitting on a melting ice cube and how to pivot to "distribution + atoms." - The Gambling Epidemic: Why the next massive healthcare crisis is happening on Robinhood and Polymarket. If you want to know what high-conviction, mission-driven execution looks like in 2026, this is a must watch. 🔗 Link in the comment section

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Peter Reinhardt built Segment into a $3.2B company, but it took years before they figured out *how* to find product-market fit. They finally realized they had to give up control over the vision to their users, and the market took it from there. His ambitions have only grown, and he's now CEO at both Charm Industrial and Revoy. If you're struggling to find product-market fit or figuring out how to maintain it as you grow the company, you won't want to miss this episode. Listen Peter Reinhardt and Calvin French-Owen tell the full story at https://lnkd.in/gay_2Gc3

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The Real VC Shift? It’s Not Just About Firms Evolving—It’s About Who Gets to Play. I have seen a lot of posts on people talking about how the traditional VC model is dead. Lightspeed becomes an RIA. Sequoia goes evergreen. General Catalyst buys a hospital. Thrive builds HoldCos and AI-native ventures. All of this is a US market view. And this is one view. But having been at the centre of the early-stage ecosystem in #India — and having watched HNIs enter the startup space in waves, often driven by cycles of hype and liquidity— I think we are oversimplifying how we see this asset class. There’s another trend emerging that’s not being discussed enough: The real shift isn’t just VC firms evolving. It is how startup investing is integrating into wealth management—and how the next generation of investors will build portfolios that blend private markets, public markets, and alternatives seamlessly. In the U.S., this has already happened. Angel investing became mainstream. Founders became allocators. Platforms enabled access. In India and emerging markets, we are still early—but the signals are clear: 45–50% of wealth is still unmanaged. $4 trillion will transfer between generations in the next 25 years. HNIs want more than stock market exposure—they want access to private markets, early-stage deals, and secondaries. The future of venture isn’t "just" about fund structures, HoldCos, or AI-native ventures at the top. At LetsVenture we have been talking about integration of #wealthmanagement with #privatemarketinvesting for a while now. It is about building infrastructure and rails that bring private markets into the portfolios of HNIs, founders, and family offices, making startup investing part of every modern wealth strategy. This creates focus on who gets to participate. My belief is VC isn’t collapsing. It is expanding—into new geographies, new investor classes, and new models of access. The game is just beginning to play out in India! #VCreset #WealthManagement #AngelInvesting #PrivateMarkets #LetsVenture #HNIs #EmergingMarkets

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BREAKING: Capital One is acquiring Brex for $5.15B. Yes, that’s less than half of Brex’s $12.3B peak valuation. Cue the hot takes. But zoom out 👇 For early investors, this is a monster win: - Ribbit Capital led Brex’s $7M Series A in 2017 - That bet turned into a ~700x return, even after dilution - YC, Kleiner Perkins, DST, Peter Thiel, Max Levchin? All did very well This is venture capital in its purest form: - You don’t need every round to be “up and to the right” - You need one asymmetric outcome early For late-stage investors, it’s a different story: - Liquidity, yes - But nowhere near the outcome implied by 2021–2022 prices The contrast is brutal when you look at Ramp: - $1B+ ARR - 50,000+ customers - $32B valuation (on paper) Same market. Very different trajectories. Brex’s pivot to enterprise, its EU banking license, and ~$13B in deposits made it strategically attractive to Capital One — especially as banks race to modernize their fintech stacks. Congrats to the Brex founders and team! Such a fantastic run!

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Why is there still no truly customer-friendly solution for share and cap-table management? Carta charges an absurd amount for what feels like a legacy SaaS tool. Pulley, while slightly better, makes onboarding difficult unless you're switching from Carta. Their main focus seems to be just converting Carta users—with discounts, white-glove service, and aggressive outreach. The remaining players in the space? Even worse from a product perspective. To Pulley's credit, at least you don’t need a lawyer to get started. #startup #siliconvalley #sanfrancisco

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Browserbase is shipping (insanely) good content right now 🔥 Fresh off a $40M Series B led by Notable Capital alongside CRV + Kleiner Perkins, they just hit a $300M valuation and are scaling fast across product and GTM. What’s working: 1. Founder-led momentum – sharp messaging across LinkedIn, blog, and product updates. The team knows their ICP and it shows. 2. Education as leverage – deep tutorials, clean explainers, and smart content that actually helps their audience build. 3. Customer proof – Perplexity, Vercel, 11x. Big names, real traction. The logos speak for themselves and drive credibility. 4. Building in public – consistent updates, early insights, behind-the-scenes wins. Strong magnet for talent + early adopters. Browserbase is showing what it looks like to earn trust with content—and ship fast while doing it. Very hyped for the team - highly rec following along.

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The SaaS model is hitting a wall. Seat-based pricing is obsolete in an economy where AI agents replace human seats. If your software requires a human to click a button for you to charge a fee, your revenue will collapse. Aggregate Net Revenue Retention (NRR) across top-tier SaaS has dropped toward 100%. Investors have already erased billions in market cap. The "SaaSpocalypse" is a structural rejection of rigid, non-automated licensing. The Solution: * Usage-Based Pricing: Shift from "seats" to "outcomes" or "compute." Charge for the work performed, not the humans present. * Modular Architecture: Enable "vibecoding." Users must be able to use natural language to build custom features on top of your core logic. This is the "DIY SAP" era. * Agentic Integration: Software must become an environment for AI agents, not just a UI for people. Static software is legacy software. Adapt the architecture or exit the market.

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The math on PvP-driven organic growth: → 1 competitive match involving 2 friends → 1 of them invites 2 more players to even the odds → Those 2 players each invite 1 more → 1 match → 5 installs, $0 UA spend Now run that loop across 100,000 daily active players. This isn't theory. Studios with structured competitive infrastructure see it happen. The unit economics of rivalry-driven growth are simply different from anything paid UA can offer. Athlos is the only service offering this in-game to studios, with minimal dev hours on integration.

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Product-market fit genuinely feels different...and it'll show up in the data Demo to close rates are the easiest thing to look at for product-market fit right now. Vertical AI startups in our portfolio are seeing 50%+ demo to close rates, even with brand new account executives selling the product. It's happening in every market from AI takeoffs to AI CSR/Voice software to AI procurement solutions. When you see a demo to close rate over 50% chances are you have a jaw dropping customer experience and you should put your foot on the gas. If you're seeing something dramatically lower in mid-market or SMB ACV categories, it's worth revisiting your product and/or your pitch.

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Three Things I Learned In SaaS, Sports, Tech & Live Events 1. The FTC is finally cracking down on brokers. Key Investment Group is the first to draw the agencies’ ire, but they won’t be the last. The FTC effectively called its next shots by listing companies similar to Key and putting them on notice. Key’s defense is similar to that of many brokers: “Other people are doing it, and Ticketmaster is the bad guy, so we should be allowed to break the law to illicitly profit from an industry we bring no value to.” Putting aside how hollow an existence it must be to spend one’s life in a business built solely on ripping people off, there is an interesting trend bubbling up that we’ve mentioned here before: They’re starting to get caught. And they have no leg to stand on. “The guy next to me was speeding too” doesn’t get anyone out of a speeding ticket. Too many are ripping off content providers on a massive scale. It would be a terrific use of taxpayer dollars—and an easy PR win—to hold these brokers accountable. I hope they do. And I hope the penalties are real this time to deter others from mirroring what Key and others before them, like Wise Guys, did. These actions will have significant downstream effects. The secondary marketplaces will feel it first, starting with Vivid. FTR: I actually like the honest brokers. It’s dishonesty I loathe. 2. That Brand Name Isn’t What It Once Was We recruit a lot. As such, we often receive résumés from companies we recognize. Some of the common names we’re told are positives: GrubHub, StubHub, Eventbrite, Vivid Seats, etc. There’s a common theme in these businesses: their stocks have cratered. For years, we watched companies grow without discipline—or real profit. I feel for those caught in the fallout now. When I’m looking for a top executive, I need someone who knows how to build a business that can turn a profit. Not someone whose only experience scaling is throwing money around. That’s the easy part. And we can’t pay for that experience. It isn’t a positive—it’s a big negative. 3. “Impossible Is Just Something to Do.” – Phillip Brooks (aka CM Punk) We started a small business for my high school son this month. He’s learning about arbitrage, profit, taxes, state licenses, and legal compliance by running a collectibles business we’ve incorporated in California. I gave him seed money to fund his company and told him he’d need to make a return on it before college. That’s our goal together. He asked: “What was the return on your investment in TicketManager?” It’s hard to calculate with other investors coming in later, but here’s the simple math: Joe, Aric, and I invested a total of $67,000 between the three of us in August of 2007. The last valuation: $110M+ (not including salaries and bonuses along the way). CM Punk, in tears reflecting on how he had just achieved his childhood dream of main-eventing WrestleMania, offered a new mantra in our home: “Impossible is just something to do.”

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Consolidation is creating compounding chaos. Every acquisition adds another tech stack. Another CRM. Another portfolio system. Another layer of complexity. Most aggregators just absorb the mess and move on. Jim Dickson didn't want to repeat that cycle. When he launched Elevation Point, he built an accelerator—not just another roll-up. That means taking control of data from day one and putting it to work in a compounding, impactful way for partner firms. We're honored to be their data infrastructure partner. Already deep in the build—connecting Practifi, Salesforce FSC, Addepar, Orion, Goldman Sachs FICC and Equities and everything in between into one unified layer and a world class application and workflow layer. Real-time dashboards. Automated workflows. Data that compounds value instead of chaos. This is what intentional growth looks like. Excited for what's ahead with Jim and the entire Elevation Point team. 🔗 ThinkAdvisor coverage in comments

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Early investors in Brex just saw 700x+ returns. Capital One acquired the company yesterday for $5.15 billion. Headlines focused on the "haircut" from Brex's $12.3B peak valuation in 2022. But for pre-seed investors who backed two 22-year-old Stanford dropouts in 2017, this is a monster outcome. YC invested at the pre-seed. Ribbit led the Series A soon after. The company was worth basically nothing at that point - two Brazilian founders pivoting from a VR idea three weeks into the accelerator program. This is the power law in action. The catch is that you had to believe in two 22-year-olds with no US credit history pitching corporate cards for startups. Most people wouldn't have (and I'm sure most people that they pitched didn't). That's the trade-off with early-stage investing. The upside is astronomical. But you're betting on founders before the data makes it obvious. Just like my Uber v. Anthropic post earlier this week, by the time everyone agrees something is valuable, most of the returns have already been captured.

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CAC (cost of acquisition) gets a lot more attention as you raise later stage rounds. But it’s not a perfect benchmark. For example, our CAC at UserEvidence over the last 6 quarters has been about $80k, and new business ACV about $43k. At first glance, that seems pretty inefficient, spending $80k to get a $43k client. To be fair, we use a pretty conservative CAC measure (thanks to CJ Gustafson from Mostly Metrics) that takes all of S&M (Sales+Marketing - which includes CSMs as well) divided by the number of new biz deals. And yes, I'm not super proud of that metric or anything - we aim to be a lot more efficient this year, and these numbers could be improved significantly. But - in our strategy, which over the last couple years has been focusing on the mid-market and larger enterprise segment - it can still makes sense. Here’s how: We have a strong renewal rate and upsell/x-sell motion which leads to strong NRR (averaging over 115% the last 2 years). For example, 12 months ago we landed a $25k pilot with one of the top 4 cloud vendors. <9 months after we started the pilot, we had expanded to 6 additional business units and ARR went from $25k to $285k/yr. Strong NRR leads to strong LTV (life-time value of a customer). So if you look at CAC vs LTV - the ratio starts to look a lot better. In other words, I’m OK losing some money on the first year of a deal if I have strong confidence that customer is going to stick around and expand. Now, not all businesses are the same, and we’ve raised a significant chunk of VC money. If we were self-funded we’d have to have different goals and a different playbook to get there. But as a founder, while you need to know all your VC metrics, those metrics are still just guidelines and yardsticks that should be contextualized against the backdrop of your broader market, strategy, and cash/runway position. In our case, we have strong conviction that customer marketing/advocacy is a growing market, strong conviction we can eventually own that market (and potentially adjacent markets) if we execute well, and we have the cash to pursue the long-term strategy needed to execute. Understanding and communicating the whole picture is key to inspiring confidence with your board, investors, and team.

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Oh, casual note from Claude that your OpenClaw calls are going to charge you actual $$$s, instead of going towards your $200/mo subscription. So now you know why we're building Chompute - largest open weight models - no usage limits - pricing by agent calls, not tokens - predictable cost From Claude email: One note: starting April 4, third-party harnesses like OpenClaw connected to your Team account will draw from extra usage instead of from your subscription. If your team doesn't use them, nothing changes. If they do, the credit and bundles above have you covered.

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Well, that flipped quick. B2B SaaS died overnight and hard tech and deep tech is primed to take its place. It’s good to see people excited about building things you can touch again. B2C is about to have a renaissance as well.

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