JT Garwood

SCOOP: Swish is raising $30 Mn in a fresh round at a valuation jump of over 2.4X within a year of its last fundraiser. What stands out isn’t just the capital, it’s the timing. The 10-minute food delivery model is proving harder than expected. Several large players have already pulled back, citing operational complexity and uneven demand. Yet, Swish is doubling down on the same playbook with a hyperlocal, cloud kitchen-led approach. This is what makes the bet interesting. In consumer internet, outcomes are rarely linear. Categories often look unviable until someone cracks execution. Swish is entering a space where others have stepped back. That could either mean the model is broken, or that it’s still early.

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Recko’s $150M Exit to Stripe. I sat down with Co-Founder Saurya Prakash Sinha to unpack the story behind one of India’s biggest B2B SaaS acquisitions — and what it really takes to build for a $100M+ outcome. We dive deep into: 1. Why companies get acquired? 2. How companies are evaluated for Acquisitions? 3. Why $100M+ Acquisitions are rare? 4. How to Build if there's Zero Validation? 5. Why Stripe understood what VC's couldn't 6. How to raise when investors follow success playbooks? 7. How to find the real value your product adds? 8. What to expect when building products in finance? 9. What did Recko solve for Myntra that Big Four couldn’t? Watch the full episode: Youtube: https://lnkd.in/gwW84mur Spotify: https://lnkd.in/gGHMCqV8 Apple: https://lnkd.in/gDSesRm3

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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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Founders obsess over valuation. Investors obsess over terms. Only one of these determines what you actually walk away with. Today’s new HealthVC breaks down the round math that silently shapes founder outcomes. How preferences reshape downside. How participation erodes liquidity. How anti-dilution moves future pain. How option pools rewrite ownership. How pro rata defines who stays powerful as you scale. If you want to protect your future self before signing a term sheet, this is the edition to read.

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If you're relying on one revenue stream, it's going to be hard to stay competitive in almost any market. The irony is technology expedited this. As everyone knows, the most common reason for startup failure is "lack of capital." Many seem to assume this is related to venture funding or misallocation of funds. That could be part of it - But those are normally a symptom of the illness. The core problem is lack of cash flow. Or rather, free cash flow. In other words, having a bad business model. It's having to work too hard or spend too much money to generate cash (Recurring or not). This is true for a product or service business in any industry. Generally speaking businesses that succeed have done a good job of these 4 things: 1. Getting people in the door 2. Getting them to spend money 3. Getting them to spend more money 4. Getting them to do it over and over again Everything else is just nonsense or vanity. You can have an amazing idea, an amazing product, target a growing market and still fail without the above. In fact, it's pretty easy nowadays considering how easy it is to build products and identify growing markets. Many overlook this. Many overlook the fact that the "health bar" in business is only one thing - Your bank balance. You can have a terrible idea in a regressing market but if you have money in the bank - You still have options - The game isn't over. People love to talk about pivots. Well you can't pivot if the health bar is at 0. Similar to life itself, everybody has a million problems until they have a health problem - Then that becomes the only problem. The goal of business at its root is to keep the game going. To survive. "Thriving" is somewhat of a luxurious construct that is a product of media and content. The best way to "be competitive" is to survive because the greatest killer of competition is time. And this cannot be done without free cash flow. Media has made it difficult for people to think over a long time horizon due to how business content is framed - "It only took me 2 months to make 17 trillion dollars. Here's my secret." Once again - Time is the greatest killer of companies. But it is also the greatest friend to companies that succeed. It's a paradox. Without placing great importance on the core principles of what makes businesses succeed - Over a long enough time horizon - The market will just run you over.

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A lot of office hours sessions are a good back n forth going over the options that people have for their businesses, but a big chunk is putting Founders and fund managers in touch with people and vendors who can help them execute on those options that we've laid out for them. Advice is the name of the game, but the resources, connections and referrals that we make are a lot of the value that they get. Actionable steps and referrals/intros to the right people to help get those things done is where they get their money's worth!

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Fundraising isn't dating. It's a sales funnel. And most founders don't track it, so 3 months go by while they're still "in conversations." Here's the brutal math (seed round, current selectivity): 100-200 investor outreaches → 15-20% reply rate → 15-30 first meetings → 5-10 partner meetings → 1-3 term sheets → 1 close If you're not tracking conversion at each stage, you're not fundraising. You're hoping. Founders who close faster don't have better luck. They have better systems: 1. They track the funnel weekly Where are leads dying? Outreach, first meeting, partner meeting? Each bottleneck has a different fix. 2. They iterate the narrative Every week: one sharper answer to the question that killed the last meeting. 3. They batch meetings 10 meetings in 2 weeks beats 10 meetings over 2 months. Compression creates urgency. Urgency creates leverage. 4. They treat "no" as data A fast no is worth more than a slow maybe. It frees you to find the real yes. If your fundraise feels stuck, stop asking "Who else can I talk to?" Start asking "Where is my funnel breaking?" I stress-test fundraising packages for founders. Deck, model, cap table, assumptions. You get a written findings memo and a 90-minute call showing you what breaks before investors do. Link in comments. #fundraising #seedstage #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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You can turn $100,000 into a $50 million business through acquisitions. This is closer to capital allocation than traditional entrepreneurship. Here's the deal structure. First, the capital stack. You buy a business the same way you buy a house. Equity in, bank covers the rest. With SBA loans: 90% loan, 10% equity. A million dollar business might require $100K to $200K down. Target companies with $1 to $3 million in earnings. Go to sellers that are NOT at market. Brokered deals are competitive and sellers want cash at close. This only works off-market. Here's what you propose: Seller keeps 20% equity in a new entity. Asset sale, their company moves into newco, they keep running it at fair market salary. You write them a check for 60% via bank loan. Remaining 20% is a seller's note: 10% straight note, 10% performance earnout. From the bank's perspective, you created 40% equity. The truth? It's really only 20%, and it's the seller's. Your money in? Approaching zero. But you own 80% of Enterprise Value. Why would a seller agree? Tell them: my goal is to make your 20% as valuable as the 80% we're giving you today. What are the odds you double the value on your own in 3 to 5 years? Now stack earnings. $2 million average per company. Buy 10 just like this. $20 million combined earnings under one entity. Centralize marketing, accounting, HR, governance at HQ. You bought each at 4 to 4.5x. A $20 million earnings business sells for 7 to 7.5x or more. That's multiple expansion, just by combining them. Close the first one. Negotiate the next $100K for the next business. Then newco sells to PE for 7, 8, 9x your $20 million in earnings. That's the path from $100K to $50 million. If you're considering buying a business in the next 12 to 24 months, we built Acquisition Lab for exactly this. walkerdeibel.com

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Great overview of the Florida VC ecosystem 👇 What stands out is not just the ~$2.85B raised, but how distributed and specialized each region is becoming. • South Florida → crypto, fintech, LatAm access • Tampa Bay → strong early-stage pipeline • Orlando/Space Coast → deep tech, defense, space • North Florida → emerging operator-led funds Tax advantages help, but the real story is growing density of founders, angels, and operators building locally. Still early compared to SF and NY, which is the opportunity. Who are the next Florida-based funds or angels getting active?

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Secondary sales at Series A & B are booming. But did you know 90%+ of founders don't maximize QSBS during secondaries? Most founders leave $3M+ on the table for every $10M of sales. Here's why - First, these rounds are happening earlier & earlier in companies lives. Big rounds, $20M+, are now very common at the Year 2 - Year 4 mark. This is much faster than in the past. Because of the high demand to invest in these businesses, I am seeing a lot of secondary sales. Anywhere from 5% to 20% of the funding amount is being paid back to founders. The unfortunate thing here is that founders think they are missing out on QSBS with the secondary sales due to early sales. A quick reminder - when you sell before Year 5 you do not get QSBS. Unless you do a QSBS Rollover. So, for founders who are taking secondary & feel like hope is lost on getting QSBS, that may not actually be the case. A QSBS Rollover can bridge the gap to hit the 5 year mark to get QSBS.

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