Greg Smyth

I met a YC founder who raised $3.5M, but kept the team to 3 people. He took 2 years to launch— then grew 10x to $2M ARR in a year: Benji built an end-to-end recruiting platform with just 3 people. Today, he raised a $50M Series D. Since 2022, he grew Ashby from 70 to 220 employees—and 2,700 customers. He hit $200K ARR the year he launched— then 10x’d to $2M ARR the year after. I asked Benji why it his end-to-end solution worked when so many “one stop shops for X” fail: 1. There were big unsolved pain points. 2. Existing vendors were small companies.  3. It was possible to build a bundle of best-in-class products. “If you can give people 1 product that works better than 4 products without losing functionality…people will be happy to use that.” It sounds too easy— and it is. Benji was a Director of Engineering, where he spent 90% of his time hiring— he experienced the problem first-hand. He thought about his idea for 18 months before going all-in. He had 100 conversations with potential customers before he started building. He graduated YC, raised $3.5M, but didn’t hire anyone. He kept his runway long. It wasn’t just turning 4 products into 1. Benji understood the pain point, the customers, and the space. He succeeded for the same reason most startups do: He put in the the work— the unsexy, everyday work. The work behind the scenes. The work that doesn’t make headlines. The work you never see. /// Listen to the full episode with Benjamin Encz on The Product Market Fit Show #startups #venturecapital #founders

244

25 Comments

Most people don’t exactly love their insurance company, and the data backs it up. Incumbents are scoring shockingly low with customers: - State Farm: 1.5 stars on Trustpilot, 3.9 on Google, and 1.23 on BBB - Allstate: 1.2 stars on Trustpilot, 3.0 on Google, and 1.12 on BBB - Universal P&C (largest in FL): 1.5 stars on Trustpilot, 3.2 on Google, and 1.28 on BBB Meanwhile, Kin Insurance is flipping the script: 4.9 ⭐ on Trustpilot, 4.7 ⭐ on Google, and 4.59 ⭐ on BBB Kin’s tech-first approach makes pricing more fair, service faster, and claims smoother. It’s a completely different experience for homeowners, and customers are singing Kin's praises in reviews. It's exciting to see such a massive gap between a challenger and the old guard. Kin is showing us that insurance doesn’t have to be broken. Proud to back Sean Harper and his team, who are raising the bar for the whole industry!

150

22 Comments

One of my VCs sent this in a group chat. Garry from YC reposted it. Some VCs are now celebrating something called "Grindscore". A metric that rewards companies where work-life balance is low. You read that right: the more miserable your team, the better your score. The logic? “Figma worked this way!” No. Low Work Life Balance = high turnover, lack of focus, burnt out teams. Can we stop glorifying sacrifice and drop workalhosim as something to be proud of?  Where does the insecurity even come from? You don’t need 80-hour weeks to build something great. This isn’t investment banking. To really win? Make fewer, better decisions. Prioritize quality over hours. Kill useless meetings. Sleep. Avoid scope creep. We don’t need more grinders. We need teammates who can protect their focus to do their best work. Who are self-disciplined with a huge amount of ownership. Who protect their calendars. What if the real KPI is: How many people want to stay in your company for 10 years and still make it home for dinner? (Or are even already at home because they chose to work from there that day.) Who understand that it takes time to build great companies. If anything, building a great company should go hand in hand with building a great place to work. That’s been our mission at Sarwa alongside building wealth. Creating a culture and a work environment we’re proud of. If you want proof, look at how much we are shipping and our results. The largest product suite in MENA across investing and trading. Billions in trading volume. Profitable. With leadership tenure near 6 years and company-wide retention most startups would envy. Calm, consistent, and compounding. Some of the most successful companies on the planet were built by founders who rejected hustle culture: “We don’t celebrate grinding. We celebrate impact.” — Tobi Lütke (Shopify) “You can’t be creative when you’re burnt out.” — Melanie Perkins (Canva) “Calmness and craftsmanship go hand in hand.” — Ivan Zhao (Notion) “Workaholism is a disease. It’s not a badge of honor.” — DHH (@basecamp) “Balance isn’t a perk. It’s part of building a company people don’t want to leave.” — Scott Farquhar (Atlassian) “We optimize for asynchronous communication and deep work. That’s how great things get built.” — Sid Sijbrandij (GitLab) “You can build a billion-dollar business with calm, remote work.” — Wade Foster (Zapier) “Work had to be enjoyable, or it wasn’t worth doing.” — Yvon Chouinard (Patagonia)

103

11 Comments

Friday rant time. Investors don't take risks. Everyone wants Tier-1 background.  Nobody is out there for the little guy. Sharing a brief breakdown of VC economics (deep dive link in comments). VC is NOT charity, it's pure financial services. The NUMBER ONE metric we're measured by (for older funds) is DPI, fancy term for how much money you've given back. 1x, shut shop and go home. 2x, better, but still bad. 3x, now you have a reason to live. (for folks wondering how young funds are measured, it's typically MOIC + IRR, basically, how are companies you've invested in performing at present). Assume a ₹200 crore seed stage fund. Needs to give back ₹600 crore at least. Ignoring fees and expenses, you can invest ₹10 crore in 20 companies, for 10% each. Since it's quite clear (Fractal, Zomato, BlueStone, Nykaa) that it takes 12-14 years to IPO a startup in India, you can't wait that long (fund life is 10 years). So you have to exit to Series C/D investors who WILL want a discount. Assume 3 rounds of dilution, leaves you with ~5%, 20% discount, so 4% held. Seed has ~75% mortality rate, so 5 companies left. These 5 have to get you ₹600 crore. At 4% held: 1 company needs to raise at ₹15000 - Just NOT happening 2 companies raise at ₹7500 - Still VERY unlikely 3 companies raise at ₹5000 - Closer 4 companies raise at ₹3750 - Possible 5 companies raise at ₹3000 - More possible ^This is also the price Minimalist was acquired by HUL, which was an OUTLIER outcome and first of it's kind for consumer startups. The above should illustrate how hard the business is. Hence when funds insist on backing folks with successful exits, strong corporate careers, or absent both, just a great educational background, is maximizing luck. At Seed, there are two things that swing it for you. I call it Numbers & Story. If you have a GREAT story (I sold my last company for ₹500 crores), you can have ~no numbers. If you have a good story (I was VP Google India), once again, numbers are lower priority. If you're 22, from a small town college, breaking it down harshly, you NEED numbers. As an investor, we just DON'T ignore amazing growth. That being said, since this is a (very hard) financial business, we're looking at any and every indicator of possible success. Experience here helps in two ways: - Have already made dumb mistakes on OTHER peoples money - Have a network who will pick up the phone and help you/become first customer #venturecapital #startups #funding

455

99 Comments

Decade and a half ago two major changes ripped through the VC world: - rise of superangels (eventually solo GPs/seed funds) - rise of 'founder friendly' VCs (eg FF, A16Z etc) Now we have two changes again: - rise of megaVC - emergence of smaller firms practicing VC as craft + value add

85

11 Comments

2009: The financial crisis had crushed fundraising. Barely any new capital went into venture funds. Yet the vintages from those years went on to deliver some of the strongest returns in history. Fast forward to today (2024/2025): Venture capital fundraising is at its lowest point in more than a decade. What does that mean? - ⁠Less money will be available to startups over the next years - The bar for raising capital goes up again: quality matters - ⁠Entry valuations will reset to saner levels --> Funds raised now are likely to outperform, just as history shows The paradox of venture: the best time to commit capital is exactly when most people hesitate. Investors (Limited Partners) should lean in now, not when the next boom makes it easy.

85

13 Comments

Turns Out… My Fund LP Portfolio Beat My Direct Portfolio 😅 Maybe I’m not a bad investor — maybe FoFs aren’t the fallacy we think they are. I’ve been reading several great pieces lately and reflecting on a touchy subject: venture funds of funds (FoFs). Hamilton Lane has hammered this home for years: venture isn’t really an “asset class” — it’s an access class 🚪. • 📊 VC has the widest dispersion in private markets. • ⏳ That dispersion hasn’t narrowed, even as VC scaled — the power law still rules. • 📉 Drawdowns cut deeper here than anywhere else. Translation: pick the right managers and you look like a genius; miss them and you look… well, like me on some of my direct deals 🙃. That’s why the Pattern Ventures benchmarking caught my eye: across 2005–2019 vintages, FoFs (yes, even with “double fees”) actually: ✨ Beat direct VC in the median quartile in 14/15 vintages (+0.68x TVPI). ✨ Outperformed the bottom quartile every single time (+0.89x) — and never fell below 1x. ✨ Smoothed returns, with dispersion nearly halved (0.58x vs. 1.21x). Confession time: even in my own portfolio, my LP fund investments have outperformed my direct ones. Not sure if that makes me a bad direct investor 😅 … or just a better FoF LP. Either way, it taught me something about where my real portfolio chops lie. In hedge funds, double fees kill. In venture, access math beats fee math. So the real question for LPs isn’t: “Do we avoid FoFs?” It’s: Do we build selection capability — or buy it? Because in venture, average is the most dangerous place to hide.🚫 🔖 David Dug Skylar Anurag John Samir #VentureCapital #PrivateMarkets #FundofFunds #LPInsights #VCInvesting #PowerLaw #Dispersion #InstitutionalInvesting Asilica | Redshift Capital | Allocate

118

9 Comments