Brett Goldberg

Public software is down 40% in 12 months. The selloff has been indiscriminate. Companies hitting their revenue targets are getting hammered alongside the ones that deserve it. The market isn't distinguishing between well-positioned and poorly-positioned software companies.   That will change. When it does, the companies left standing will be the ones with moats that matter in a world where agents do more of the work.   The Emergence partnership spent yesterday debating a question I think every founder and investor should be asking (and, judging by my LinkedIn feed, it seems they are...):   Which software moats actually survive in an AI era?   Here's the spectrum we landed on (from least to most defensible):   1. Workflow   Pre-Claude, getting humans to do their jobs inside your software was a powerful moat. But if agents are doing the work, who cares about the human workflow? Cursor vs Claude Code is the canary in the coal mine: one owns the workflow, the other just executes—and developers are increasingly choosing execution over process.   2. Integrations   MCPs are rapidly commoditizing the glue between systems. Being the connector used to be a moat. Soon, it'll be a utility.   3. Data repository   Static repositories are table stakes. Owning customer data matters less than understanding what to do with it.   4. System of action   Now we're getting somewhere. If your software touches money, customers, or real-world outcomes (think Gusto or Shopify), ripping it out is genuinely painful.   5. Full context   The most important new moat in AI. Understanding how a full task gets done across systems, knowing what a user needs across many different sources. This is what agents need to be useful, and the companies that own it become indispensable infrastructure. But it's young and unproven. If context becomes portable (the way integrations are being commoditized now), this moat could erode too.   6. Brand   The moat that survives every platform shift. Trust compounds over time and can't be replicated by a new entrant with better tech. When everything else gets commoditized, the vendor you trust still wins.   7. Network effects   The most underappreciated moat in AI, and potentially the most enduring. But not all network effects are equal. Workflow-based ones (more humans in the tool) are vulnerable. Data and trust-based ones (every user makes the product smarter) actually accelerate with agents. LinkedIn, Doximity, and Slack all still have this. Relatively few AI native companies have prioritized it...yet.   --   The bottom line: Seat-based pricing and workflow stickiness were the backbone of the last era. Both are eroding. The next era rewards companies tied to outcomes, context, and trust.   If you're a founder, stress-test your moats against this spectrum. If your primary defense is "our users do their jobs in our software," you have work to do.   Because the world is moving towards selling outcomes, not software.

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Mark Leonard created $92B by quietly acquiring 600+ SaaS companies...Here's the story of an acquisition legend 👇 In 1995, Mark Leonard, disillusioned with the hype-driven venture capital world, saw an overlooked opportunity: acquiring and holding vertical market software (VMS) businesses indefinitely. For clarity: VMS companies build and sell software solutions designed specifically for the unique needs of particular industries or market niches. It got him to start Constellation Software (CSU), acquiring niche B2B software businesses with: → High margins → Low competition → Sticky, recurring revenues → Hard-to-replace products When they went public in 2006, most investors thought CSU was "overvalued." They were wrong. Since its IPO, Constellation has: • Grown over 125X • Generated $95B in market cap  • Delivered 34% annualised returns Here's how Leonard pulled this off👇 1/. Decentralised leadership. Leonard wanted a business that could scale without a typical corporate structure. So he built a nimble decentralised system: It has Operating Groups (OGs), which are holdings operating in multiple geographies/verticals and composed of dozens of Business Units (BUs). ↳ Every acquisition becomes a BU.  ↳ Each BU is run autonomously ↳ BUs have autonomy to make new acquisitions (they must hit CSU’s hurdle rate) This structure allows CSU to scale aggressively without losing operational control. 2/. Disciplined M&A. Constellation buys VMS businesses to own forever. Cash from its existing portfolio is reinvested into new acquisitions. It looks for acquisitions that can generate a return above its internal hurdle rate (above 20% for small acquisitions). Also, follows the strict criteria of acquiring companies with: • > $5M in revenue and > $1M in EBIT • Rule of 40 above 20% (growth + EBITDA margin) • Category leaders (typically #1 or #2 in their niche) • Low-competition, fragmented markets. CSU also has a data advantage as it operates 800+ VMS and has a database of 40k VMS targets. 3./ Strategic Secrecy. Mark Leonard is a ghost. No press. No interviews. Just a few elusive photos. He even stopped writing shareholder letters in 2017. But behind the scenes, he built a compounding machine that: ✓ Avoids hype and product cycles ✓ Targets overlooked businesses with real cash flow ✓ Builds moats through industry-level knowledge and decentralization What started as a $25M investment is now a $92B empire. And it’s still growing. A story with tons of insights for both acquirers and founders.

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VCs: Your competitor raised $100M from the same LP you met at a conference. What did they do differently?   They treated it like a deal-sourcing operation, not a networking event.   Here are 19 conferences to build your LP pipeline👇   Venture Atlanta Conference - VC and startup showcase TechCrunch Disrupt - Tech startup and innovation SuperReturn North America - VC and early-stage investment conference RAISE Global Summit - VC and startup investment summit Money20/20 USA - Fintech and payments Web Summit - Technology and innovation Opal Group - Family office networking Carmo Companies - Private markets networking The East Coast Family Office & Wealth Management Conference - Family office networking Marty S.- Family office networkng Life Science Nation (LSN) - Real estate investment 22nd Annual Global ARC Boston - Alternative risk conference for institutional investors DC Finance's Global Family Office & High Net Worth Community - Family office networking California LP Summit - LP and institutional investors The Florida Family Office & High Net Worth Conference - Family office networking Florida Venture Forum - Early-stage VC and startups Angel Capital Association - Angel investor networking Institutional Limited Partners Association (ILPA) - Institutional LP and private markets SuperVenture North America - VC networking   If you meet just 3 meaningful contacts per event, that's 57 potential opportunities for deals, partnerships, or LP commitments. And that's being conservative. Most events offer way more than 3 quality connections if you work them right.   The difference between a $10M fund and a $500M fund is how you work the room!   Which ones are you hitting in 2025?   🤝 Follow me for proven strategies that help VCs close more deals, raise larger funds, and build lasting LP relationships.

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“Why aren’t you investing in YC deals?” Because the math sucks. They’re getting funded on $25mm SAFES. ”But big VC firms are backing them, those guys are smart, why would they do that?” Because they can throw $100mm in on later rounds and make 10x on a much larger amount. _________________________________________________________________________ Bill Gurley of Benchmark fame posted on X last week about how the math really works for these YC deals. For most small and medium sized VCs, they invest in your seed because they think that stand alone investment will have a good ROI. But for mega-funds? The math is different. That first $1M check has almost nothing to do with returns. It's a call option on future rounds. As part of the deal, they get rights of first refusal on future financings. If the company becomes the next big thing, they're positioned to deploy $100M+ at attractive terms. If not, they write off the $1M. It’s not new really. We saw the same thing in mobile, cloud, and crypto. When there's a new technological frontier, the largest funds can afford to buy options on the whole market. The challenge is it creates a weird dynamic where companies raise at valuations that often only make sense for the largest players. Anyone who can’t write of millions in “exploratory” investments are effectively locked out. (That’s why we focus on investing in great teams, at reasonable valuations, who we know can ship). It also puts the founders of those companies unknowingly at risk. They love getting the blue chip investor in the door, mistaking the call option for genuine conviction. They don’t realize that when the big investor doesn’t participate in the follow-on round, that’s a huge red flag to other investors. And with a $2M total seed round, with SF expenses, the money goes fast. You’ll likely need to hit $1mm in revs to justify an upround. I’m not saying don’t take the money, please do. I’m just encouraging you to make sure you have enough to execute on your plan. And remember, everything takes longer than you think.

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Never underestimate the ability of a VC to get a deal done if they need to desperately put ‘points on the board’, i.e start a track record at firm or to show themselves building portfolio in a hot space. They will move quickly at high prices. LP/return concerns are waived.

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😤 In about 2-3 years, VC will just be PE for start-ups... Going from value-creators to broker-dealers. Here's why: 👉 The IPO and acquisition market is neither vibrant nor compelling as an exit strategy. Too long of a horizon and lots of regulatory hurdles. 👉 The secondary market is booming -- 5x growth in the last 13 years -- as matured start-ups and their investors seek liquidity. 👉 Private equity is moving into the start up category. PE exits for VC-backed startups jumped from 8% (2010) to 24% (2023). What this means: more VC funds will aim for secondary exits to juice DPI for their LPs and liquidity for founders. This is what Lightspeed is anticipating with their RIA registration. 👉 AI is flattening the capital needs for early-stage venture development. Founders don't need 7-figure checks to build products, gain traction, and grow revenue. Sometimes they don't even need checks at all. 👉 Early VC rounds are looking like later rounds of 5-10 years ago. More revenue and better unit economics are expected, even at seed stage. What this means: VC's value prop from inception to seed (e.g. when technologies and products are de-risked) is dwindling, and better focused on growth on scaling. Net net? traditional VC is being pushed out of both early and late-stage start-ups, being left with a middle-stage focused on growth. LPs don't want to ride a 15-year wave anymore, nor should they. The best VCs will adjust to this and offer tailored solutions to these middle-stage startups. #venturecapital #startups

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PSA: Valuation when you raise ≠ Valuation for M&A 📣 Tough love ahead for founders who raise $... 🚫 Just because you raised money at a certain valuation... Does NOT mean you'll automatically sell for that number or more. 🚫 *** Sometimes when I take calls with founders who'd like to sell, they'll say, well, we raised at a certain valuation, so we're looking to sell for more than that. But then we'll dig into their numbers, and their EBITDA does not support a sale price anywhere near what they're hoping for. You see, most buyers want to pay some version of an EBITDA multiple. In other words, your valuation when you sell is based largely on EBITDA, plus other value-adds. But your valuation when you raise money is calculated differently. And honestly, I have no idea how it's calculated! Because I don't live in the world of venture capital. But it's clearly not calculated based on what a buyer would pay for the business. 🔹 Remember this when you go to raise funds. VC-backed companies get a lot of kudos when they raise money, and those that sell get a lot of kudos for that milestone as well. But you have to create tremendous value in between — and by value, I mean EBITDA — if you're going to sell the business for the number you raised at. Because when you go to sell, the buyers don't give a damn what you raised at. They are one massive step removed from your raise. In fact, to most buyers, your raise is irrelevant, other than knowing that founders who raise often want to pay back investors, so they'll be looking for a certain price tag no matter how well the business has performed... And that means the deal is less likely to get done. 🔹 Buyers only care about the value they're getting from you. *** "But we're not looking to sell on an EBITDA multiple." This is often what I hear after gently explaining this mismatch in expectations. Of course you don't! Nobody does 😅 But outside of a tiny fraction of strategic deals — and remember, most strategic deals happen when the buyer approaches the seller — most of your value is in your EBITDA. Yes, it's also in the brand you've built and the community you've grown and the IP you've cultivated. But those are best as value-adds, layered on *top* of EBITDA. Because most buyers want EBITDA first and foremost. To give yourself options when you sell, find ways to do all of the above. Generate EBITDA *and* win at all the intangibles that lead to revenue. That's how to get buyers to pay top dollar. But don't go into conversations about a potential exit expecting to sell for more than you raised, simply because you raised. M&A just doesn't work that way. *** I'm Alexis Grant, founder of They Got Acquired. For stories of founders who sold and how they did it, sign up for our newsletter. The link's in my bio.

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Scaling isn't hard. Scaling without culture is. Most founders obsess over growth metrics. ARR. Headcount. Funding rounds. But they forget the invisible foundation that holds everything together. Culture isn't ping pong tables and free snacks. Culture is belonging. And belonging comes from one thing: Cadence. The Monday email you send to your team. The weekly culture call where someone shares a book they love. The consistent appreciation you show for the janitor and the COO equally. Every Monday. Every week. Every interaction. When systems break (and they will), culture forgives. When you write that email on a bad day... Culture gives you the benefit of the doubt. When market conditions shift... Culture rallies around the vision. Here's the truth most leadership gurus won't tell you: You can't define culture before it happens. You can only build it through the daily cadence of communication and care. I write my top 10 wins every Friday. We used to have 30-minute culture calls every week. Someone would share one thing they loved. Could be a book, a story, a Wikipedia page. Simple? Yes. Easy? No. Transformative? Absolutely. While your competitors chase vanity metrics... You're building something that scales infinitely: People who believe in the mission more than the paycheck.

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The deal was nearly closed. A top-tier VC was ready to sign and wire. Then an early investor killed it... overnight. A founder recently emailed me and my colleague, Andrew Berg (shared with permission), which left me frustrated, sad, and angry. They raised pre-seed capital from a non-traditional investor (think hedge fund manager type) who ironically brands themselves to “partner with founders to build great companies.” The company’s multi-year journey ended, not because of market fit or founder execution, but because of misaligned capital. It’s a painful reminder- who you let on your cap table matters a lot. Get references before you take someone's check! Not all money is long-term aligned. And not all investors play the long game with your best interests in mind. #startups #venturecapital #founderlessons #evilinvestors

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If you look at the early-stage fundraising funnel, conversion rates are tightening, but the companies that do raise are doing so at higher valuations and with larger checks. The market seems to be betting on fewer winners, but those winners will be bigger. I’m not convinced. I do believe the very biggest winners will be larger than ever as AI expands the reach of technology, largely by replacing labor. But I don’t believe there will be fewer winners overall. Most B2B solutions are moving toward verticalized, specialized use cases that deliver superior value compared to generalized horizontal platforms. That shift should create more winners. While these vertical players may not reach the scale of the horizontal mega-winners, they can still generate the kind of multibillion-dollar outcomes that venture is built to fund.

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If I was a founder again today looking for a pre-seed VC who gets it and actually cuts checks pre-revenue, here are the 10 pre-seed investors in my rolodex who I would call first. All of them are fantastic Did I miss anyone? 1. Outside VC 2. Outside VC 3. Outside VC 4. Outside VC 5. Outside VC 6. Outside VC 7. Outside VC 8. Outside VC 9. Outside VC 10. Outside VC

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Venture capital benchmarks are complete fiction. I track real performance data on ~200 emerging manager funds. The public benchmarks everyone quotes use flawed methodology that makes the industry look better than reality. When you strip away SAFE caps and speculative valuations, focusing only on priced rounds, the numbers tell a different story. Top decile funds are printing money at 2.7x+ TVPI, beating the performance of the top technology stocks. Top decile: 2.7x+ TVPI Top quartile: 2.2x+ TVPI Mean: 1.2x TVPI Stop comparing yourself to fake benchmarks. Start comparing yourself to real performance. The methodology matters more than the numbers. Do your homework before you believe any benchmark.

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📈 Some recent headlines from July '25 in Boston's venture backed world... -We've got acquisitions -We've got fundraisings -We've got announcements & releases -We've got content from around The Hub -Coin Metrics is acquired by Talos for (reported) $100M+. Congrats to their team! -Snyk acquired Invariant Labs (undisclosed $$) -Insurtech Ledgebrook raises $65M Series C for excess & surplus insurance -Remark raises $16M to build out human-powered expert models for e-commerce -AllSpice.io raises $15M Series A to launch AI agents -H2Ok Innovations rasies $12.5M Series A to modernize process manufacturing. Congrats Annie L., David Lu & team! -LogicFlo AI raises $2.7M to arm every life sciences expert with their own AI workforce -HelloPrenup announces new investment from The Legal Tech Fund -Alexander Ng and Rebecca Patterson launch JoyFi to help couples with their finances -Clasp passes $100M in employer backed student loan support for healthcare -David Chang leaves Hunt Club / Ari Fine Glantz is stepping down from NEVCA after 10 years. It's not goodbye...it's see ya later -Eric Paley from Founder Collective is appointed MA's next Secretary of Economic Development. Your success is now our success! -Jellyfish releases their 2025 State of Engineering Report - 90% of teams using AI / GitHub Co-Pilot top tool -Cimulate AI announces CommerceGPT and Cimulate MCP Server -Realm.Security, Inc releases industry-first AI-Native Security Data Pipeline Platform -Lila Sciences and Liquid AI were recently highlighted by MGMT Boston -The Summer Working Chronicles Episode 1-6 are live from Downtown > Kendall > Back Bay. Check them out! -Rho is expanding their team into Boston. If you're looking for a new standard in business banking, check them out! -Tess Michaels from Clasp, Karen Kelly 🌈 and Stephan Smith from Launch by Lunch 🍕, Jonathan Chang from Markit AI, Emily Knight and Benjamin Downing from The Engine (+others) joined 🔥 The Lantern 🔥 to talk about what they're working on, have learned, and are seeing in the market! More on the MGMT Boston news feed. Follow along!

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So hot right now. Looking for Founders to build funded companies in a few hot spaces! VCs get a lot of flak for trend chasing (and rightly so), but a lot of times, things are hot for a reason. Forum Ventures we are building companies against two hot VC trends right now:👇 1️⃣ The AI Agent Application Layer – What still needs to be built for AI agents to take the next real step forward? The infrastructure is maturing, but the applications that truly unlock value are still in flux. 2️⃣ New Administration, New Markets – In case you missed it, the U.S. has a new president, and policy shifts create market shifts. Market shifts create startup opportunities. Simple as that. Here are five B2B SaaS startups we’re looking to launch: 💰 AI Agent Payments – The financial layer for AI agents, enabling them to initiate and process payments autonomously. ✈️ Automating Compliance for Aerospace & Defense – Mid-market aerospace suppliers are buried in outdated systems. AI-driven compliance and audit automation can fix that. 👨‍💼 Insurance for AI Agents – Bridging the gap between legacy insurance and the emerging risks of AI, so companies can get coverage that actually makes sense. 🏗️ Surety Bonds, Simplified – AI-powered underwriting to speed up approvals and scale surety bonds efficiently. 📲 Voice AI for Regulated Industries – Healthcare, finance, insurance, commerce—highly regulated industries need AI-driven voice solutions that meet their compliance standards. We’re actively recruiting founders to launch these companies through our AI Studio. Full blog below 👇

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Here’s the networking loop I used to land VC interviews I had no business getting. 1. Build a focused target list (25-30 funds, people 1-2 steps ahead of you) 2. Turn every convo into the next one (“Who else should I talk to?”) 3. Follow up with value, avoid asks You DON’T need to start with a huge network to break into VC. But you DO need a repeatable system to build one. #venturecapital

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