Paul Krugman’s essay The Billionaire’s War covers why the wealthy won’t feel the consequences of Trump’s war; instead they’ll fall on the mainstream American. His has particularly harsh judgment of the technology elite.

…the vast wealth of tech billionaires has made many of them unconcerned with the little people’s lives — and deeply unpatriotic. If Americans are being brutalized and murdered by rogue ICE agents…well, that’s not their problem. If the Justice Department and the FBI are totally subverted and operate as Trump’s enforcers, they know that vindictive, unlawful tactics will never touch their lives. If Republican budget cuts decimate rural hospitals and deprive hundreds of thousands of health insurance…well, they have their own private doctors and clinics. If Trump starts an ill-conceived war that doubles the price of oil…well, they can certainly afford the higher gasoline bills for their limousines and yachts. And it won’t be their kids hunkered down in a bunker in the Middle East.

Hold aside the intensity and breadth of Krugman’s statement, I mean, it’s Krugman – I focus more fundamentally about whether the technology upper class is becoming less likely to have to deal with the negative externalities they create, and whether this implicitly changes the way they approach their lives. In a K-shaped economy without a shared definition of what is ethical or moral, one can’t help but if at least year-over-year, decade-over-decade this is true of our community.

Something Substack’s Chris Best said about their partnership with Polymarket stuck in my head: “As Best put it to me [Alex Health]: “I’m a ship and find out guy.”” Combine that with what interviewer Alex Heath posited in the same article: “To this tech leader class, the potentially negative ramifications of how these markets actually work today are secondary to the long-term value they’ll bring.” I don’t want to single out Best specifically – lots of industries and companies — most way bigger than Substack — are rushing to create partnerships like this – I just wonder if they’re all making decisions guided by upside ($$$, engagement, being in the flow) and unrestrained by the downside. What if ‘find out’ is acceleration of Gen Z gambling trends, and lives ruined? How do we balance those risks with market economy needs? With the belief that so long as it’s legal, adults are able to make their own choices?

It’s certainly no purity test that I want to force on others uniformly – I’ll leave it to each person to decide for themselves – but historically Homebrew has not invested in gambling related startups. It’s not as interesting to us and we’re concerned about the impact of turbocharging these models with tech and venture dollars. Founders of these companies likely aren’t bad people and they deserve investors who are passionate supporters of their work. If we don’t think we be that for them, then we certainly shouldn’t ask to be on their cap tables. I don’t think prediction markets need to fundamentally be a mirror of casinos but it’s certainly true that much of their marketing (and a lot of their volume) today is sports-related.

I just encourage people to have their own redlines about what they will or won’t do for money. And to keep in mind that society is based on not just climbing the ladder, but also making sure the ladder is perched on stable ground.

Tip DON’T LET AIRLINE RIP YOU OFF ESPECIALLY AS OIL PRICES CLIMB: I’m using Junova to track purchased airline tickets I’ve taking and auto-reclaim credit if the price drops. It was started by a friend and so far has recouped $2000+ of American and United credits for me. Their business model is: service is no cost, but if they successfully get you credit, they charge 20% of the value to your credit card. If you use this referral link, your first $25 of fees (ie $125 of flight credit) is free. Let me know how it works for you!

My Actual Savings This Year

You are never alone – there’s always at least one other person working through the same questions. That’s something 20+ years of blogging has consistently proved to me via private responses to my public posts. In asking about Paul Krugman’s assertions regarding our industry’s billionaires, and expanding it to include more of us (the tech elite), I received several versions of “I share your concerns but also just living in my corner of the world, trying to do good work,” which is totally normal. ‘Can you be part of the system without also being part of the problem’ is something I wonder as well. I am 25+ years in technology; I’ve held positions of responsibility on notable products; as an investor I’ve committed other people’s money – and now our own – into hundreds of startups. While you’d likely list many techies ahead of me on the current list of ‘their decisions have global impact,’ historically I’ve been in some of those rooms. So, can you be part of the system – the commercial tech industry – without also being being part of the problem? I’ve decided the answer is Yes, But….

Yes, but you have to believe that the system itself isn’t corrupt at its core. I believe in capitalism and I believe in technology as forces that have incredibly powerful and positive implications for the world.

Yes, but you should revisit your first principles and maintain dialogue with people you respect from outside of your system. You have to try to truly understand their POV and you have to know that you might be wrong.

Yes, but you need to understand how the physics of the system – the game on the field – itself influence the behaviors and incentives, why the defaults are so strong, and what you want to limit, counter, or reject. And the cost of doing so.

Yes, but it’s healthy to maintain a personal identity and variety of relationships that aren’t system dependent. It’s harder to not conform or to leave a community behind if needed when it isn’t just your livelihood but your everything.

This is a WIP list but helped articulate a basic framrwork; where I’ve been challenging in maintaining those beliefs; and what in the future could make it harder for me to *not* be part of the problem. Next step was asking myself for examples of ‘living’ those values.

What systems have I opted out from? Twitter. Even before Elon I made some meaningful changes to its role in my life and after the sale, I decided it wasn’t for me going forward.

What incentives have I pushed against? Capital We always wanted Homebrew to be small enough to be able to say ‘no’ to investments/areas that we didn’t feel comfortable with from a values perspective. Switching to using our own capital makes this even easier. One reason for creating Screendoor, which backs new VC firms, was the goal of helping new types of excellence debut in the marketplace, to the benefit of founders, and threatening those existing firms which wants to stay mediocre.

Leaving Google helped me start to build an identity outside of my job, but it was really a combination of fatherhood and new hobbies which gave me a set of people where my interactions didn’t start with being on an org chart or cap table together.

All of this is caveated with the fact we might be living in extraordinary times that I’m underestimating the trajectory, or that I implicitly designed a framework to justify my choices. That I’m ‘greenwashing’ per se, to let me stay comfortable. I’ll accept these notions and continue to challenge myself on my own and with the help of others.

It’s fun to watch folks without engineering backgrounds go DIY with AI taking the lead. My friend Austin Johnsen leads CorpDev at Zapier and in recent months I noticed his LinkedIn posts detailing the tools he built for the job. So I figured it would be a good opportunity to learn more about what he’s discovering. And thus, Five Questions.

Hunter Walk: How do you explain Zapier to people not in tech, how’d you end up there, and what’s your role there?

Austin Johnsen: I usually tell people that Zapier connects all the apps you use so they can talk to each other and do work for you automatically. If you’ve ever wished that when something happens in one tool, something else would just happen in another tool without you doing it manually, that’s what Zapier does. We have millions of users and integrate with thousands of apps. Obviously, AI is changing a lot of this, so we’re also pushing hard into AI-powered automation, so that it’s not just “if this then that” but agents and AI steps that can reason through complicated workflows on your behalf. The biggest benefit Zapier has here is that all of the things people wanted to automate with Zapier pre-AI are also all the things people want their agents to take over now, so our wealth of connections, triggers, and actions perfectly position us to connect agents to workflows.

I lead Corporate Development, which means I’m responsible for acquisitions and investments. We do 2-3 acquisitions a year, plus we have a unique, angel-scale corporate VC fund, the Zapier Fund, that does 10-15 investments a year. Before Zapier, I led corporate development at Twitch and Patreon, and I started my corp dev career way back when Twitter was still Twitter. Prior to that, I did stints in investment banking and private equity.

HW: I’m sure you get asked for career advice from a bunch of new grads or other folks who want a career in tech on the ‘business side.’ What advice do you give them?

AJ: I have two versions of this conversation. First, on the corp dev side, I try to be honest with people. These roles are pretty unique and the math is brutal. Most companies, outside the giants like Google, Amazon, etc. have a few people in corp dev, if that. Even those giants, the entire corp dev teams are probably under fifty people. Zapier is just me. We look at tons of deals, but actual deal volume is  low. That means there are very few roles, they rarely open up, and when they do, there’s no time to train someone. You have to hit the ground running. If you don’t already have the reps from banking, PE, or one of the larger tech giants, it’s going to be really hard to break in directly.

On the broader business side, the conversation is a bit easier. Companies will always need smart, ambitious people for things like business development (which I think of as partnerships vs. corp dev which is M&A) or finance. However, my one big tip for any of these business side roles is you still need to get close to the product. Nothing bothers me more than people that work at companies and never use their own products.  The most valuable business people in tech actually understand what the company builds, how customers use it, and what the competitive landscape looks like at a technical level. You don’t need to be an engineer, but you need enough fluency that engineers trust your judgment. And, while it’s probably still worth going to somewhere like Google and getting that stamp of approval on your resume, if you can find a smaller, high-growth company that will let you operate above your title, that’s going to be more valuable over the brand name every time.

HW: It’s clear you’re AI-pilled – at least in the sense that I see you sharing lots of content around the tooling you’ve built to help you do your job and live your life. What’s one thing about AI that people can’t really understand until they are building with it themselves?

AJ: How fast you can go from “I have no idea how to do this” to “it’s done” and how that changes what you’re willing to attempt.

I’m aggressively not an engineer. I don’t have a CS degree. I pretended to operate a web design business in high school, but I only built like 3 sites in Dreamweaver. I almost failed a project in college that required me to learn the barest minimum of Python. I try all the AI tools and am an early adopter, but I stuck to chat and I avoided touching code. We’ve had people in Zapier pushing this “Cursor for non-devs” idea since last fall and I tried and I was like there’s no way I’m using an IDE. Hard pass. 

This January though, I finally gave in and tried Claude Code once Anthropic added it as a tab to Claude Desktop. On day one, Claude Code told me to connect it to my GitHub account and I was like “I don’t have a GitHub account”, so it had me create one. That was my starting point. But the thing about Claude Code is that it’s like LEGOs, you just need to follow instructions, and I’m very good at following instructions. Every time I was confused, I asked it what to do, and it’d walk me through it, step by step: what to type, why I’m typing it, what each piece does. A couple of months later, and I’m now running a full corp dev automation server on my laptop that’s already way more ambitious than anything I first envisioned.

But it’s not just Claude Code. Last week, I used Claude’s Excel tool to build a full liquidation waterfall for an acquisition, which included modeling out proceeds across multiple investor classes, preference stacks, conversion thresholds, the whole thing. That’s several days of work for an analyst. It took less than an hour. I used Claude Chat to do a deep dive on churn and retention data, pulling threads across Slack conversations, internal dashboards, and financial data to build a picture of what was actually happening with customer disengagement. That kind of cross-source analysis would normally be a multi-week project for a data team. I did it in a few hours. And when I tell people this, they always immediately go, “what about hallucinations”, and honestly, people are way too anchored on that. Are the AI responses perfect? No. But are your human-produced analyses perfect? Also no. You still need to check them. But the AI can correct and iterate a million times faster. 

None of this was planned from the start. It started with one enrichment script that pulled company data into my deal tracker (replacing and augmenting an existing series of Zaps). Then I realized I could automate triaging the flood of inbound opportunity emails I get each week. Then a calibration system that injects years of deal history into every evaluation so the AI’s judgment is grounded in my past decisions and improves with each deal. Then a data room search engine across thousands of files for a live acquisition. Then a Slack bot anyone at the company can use to get feedback on acquisition ideas that’s a lite version of my full triage workflow. Each piece solved one problem, and solving it revealed the next one. 

The thing that finally made it all truly click though didn’t happen until last week when I finally integrated Claude Code with Zapier’s own SDK (shameless plug here, but it’s still in closed beta, so you can’t try it yet). The Zapier SDK allowed me to give Claude Code access to literally everything Zapier connects to, all 8,000+ app integrations. Before, I was always limited by what I could realistically connect (either via native connectors or flaky MCPs). The SDK solves that and also offloads auth management to Zapier (which is truly a nightmare, especially for someone non-technical). Finally, with the SDK, all my  context could live in one place for the first time. Everything I use (Gmail, Google Calendar, Google Suite, Slack, Airtable, Granola, Coda, Notion, Glean, Zoom, and on and on) is finally connected and fully accessible and usable by Claude. It’s an absolute game changer. 

You can’t understand that compounding effect by reading about it. You have to start building, ship something small, and let the next problem find you.

HW: And how do you think AI will change the nature of CorpDev/Strategy work at companies long term?

AJ: I think a lot about this, and I’m genuinely worried about it.

The analytical work (reviewing opportunities, building models, scrubbing data rooms, writing memos) is getting compressed dramatically. That’s already happening. I use AI daily for deal sourcing, company research, and enriching my pipeline. What used to require a junior analyst pulling an all-nighter is now something I can do myself in a fraction of the time. And the build-vs-buy calculus is shifting fast, because engineering teams can now ship in weeks what used to take months, which means the bar for “we should just acquire this” keeps getting higher. Corp dev teams are going to need to be more tightly integrated with product and engineering leadership, because the window in which an acquisition makes strategic sense is getting shorter. And it’s going to shift back to being more of a GTM decision than a tech decision because customers and traction are going to become more valuable than “I built something unique” in a world where Claude Code can recreate it overnight. 

But here’s what keeps me up at night: how do the next generation of corp dev professionals actually get good? When I started in investment banking, I had a crazy boss who had me churn out what he called “2-pagers” (brief company overviews with financials, comps, the works). I was doing maybe 20 a week, each taking a couple hours, all by hand. That work eventually got replaced by CapitalIQ and PitchBook, and now AI is replacing those too. But the reps I got doing it manually are the reason I can fly through financial statements today. I built an intuition for what to look for and what looks right and what looks off that only comes from doing the work hundreds of times. Nobody does things like this by hand anymore, and I honestly don’t know how you replicate that learning. AI is incredible for people like me who already have the expertise and judgment. It’s a massive force multiplier. But for someone just starting out who’s never had the reps? I think it’s going to be an absolute disaster. You end up with people who can generate beautiful outputs but can’t tell you if the answer is right.

Wade, our CEO, has this framework of “drivers vs passengers” – the strong performers are the ones generating ideas and taking action, not just evaluating what AI produces. I think that’s right, but it assumes you’ve already built the foundation to know what a good idea looks like. We haven’t figured out how to build that foundation when AI is doing all the reps for you.

HW: You and I both have MBAs – if you were the Dean of HBS (where you attended), what – if any – changes would you make to the program in order to maintain its relevance going forward.

AJ: One of the things HBS was always clear about is that they were training leaders, not analysts. We weren’t down in the trenches preparing financial statements – we were learning how to read and analyze them, how to ask the right questions, how to make decisions with incomplete information. I actually think a lot of that philosophy carries over into the AI world better than people might expect. The skill that matters most is judgment, and HBS was always focused on building judgment.

Where I’d push the program is on making sure that judgment doesn’t become disconnected from the underlying work. The risk with AI is that you fully outsource your thinking. You ask it to analyze a company and it gives you a beautiful answer, and if you’ve never done the analysis yourself, you have no way to know if that answer is wrong. So I’d pair the case method, which is still the best tool I’ve seen for developing business judgment, with a requirement that students continually build things with AI before they graduate. Not just a single case study about AI, not a strategy deck about AI. Build working products, automations, or tools. Get your hands dirty. The most valuable skill in business right now is the ability to go from zero to one on an idea quickly, and AI makes that accessible to people who can’t write code. HBS should be producing graduates who have that muscle memory.

I’d also push the school to require students to do hard analytical work by hand before they’re allowed to use AI for it. Build a DCF from scratch. Read 50 10-Ks and write up what you found. The value of AI is only as good as your ability to evaluate its output, and you can’t evaluate what you’ve never done yourself. Think about it the way math classes think about calculators, yes, you’ll use them eventually, but you need to understand the underlying math first or you’re just pushing buttons.

Thanks Austin!

Tip DON’T LET AIRLINE RIP YOU OFF ESPECIALLY AS OIL PRICES CLIMB: I’m using Junova to track purchased airline tickets I’ve taking and auto-reclaim credit if the price drops. It was started by a friend and so far has recouped $2000+ of American and United credits for me. Their business model is: service is no cost, but if they successfully get you credit, they charge 20% of the value to your credit card. If you use this referral link, your first $25 of fees (ie $125 of flight credit) is free. Let me know how it works for you!

My Actual Savings This Year!!!

I think Brad and I met back in the General Assembly days, which was one of the early code schools based out of NYC (interestingly, with a physical presence, not online only). He later started Common, a notable co-living starting, and now has a trade publication called Thesis Driven. Brad describes it as covering the ‘future of the built world’ and it’s a really interesting read for me. Enough so that I wanted to catch up with him via Five Questions.

Hunter Walk: For me it seems like Thesis Driven is both “one thing” and “a lot of things” [media company, community, educational programs, investment fund] but all which center on your love of, and expertise in, proptech. Is that fair? How do you describe what you’re doing these days?

Brad Hargreaves: That’s fair, although lately we’ve been a lot broader than proptech. “Future of the built world” is both awkward and the best descriptor I’ve come up with.

Technology is a part of that story. AI is having a tremendous impact right now across the real estate industry – operations, development, underwriting, design – all of it. We write about AI’s role as well as teach workshops that help real estate operators figure out how to use it. I have an education background so I just can’t keep myself away from that business.

But to our readers, shifts in the real estate capital markets are just as important. We’re at a weird moment in time right now where old mainstays – office and multifamily – aren’t looking as stable as they once were. So investors are looking at categories they wouldn’t have touched ten years ago. Cold storage, outdoor hospitality, niche industrial, healthcare housing, and more. Everyone’s also trying to figure out how to “seed fund” emerging real estate operators. It feels a lot like the venture ecosystem in ~2010.

Over the past year we’ve been using our platform to match investors with innovative real estate operators; it’s still early days but so far we’ve seen a lot of success there.

HW: I appreciate that not every essay is about AI or some technology startup – you actually do quite a lot of work on regulatory, design trends, socioeconomic and cultural changes to living. Do you find different types of reactions from the community? How much are you trying to explain ‘the now’ versus ‘the future’ in this analysis?

BH: We have a very broad scope for a trade publication. I’m sure that’s frustrating to some readers who only want to read about proptech or capital markets, but I see it all as inseparable. If you’re a PE shop or an institution investing in real estate, you can’t ignore any piece of it. You have to understand the role of AI. You need to have a grasp of cultural trends and what preferences – or regulatory policies – may be downstream of those. You must understand how financial markets are moving.

The easy path here would be to crank out reports on AI. But the future of real estate is also about social and demographic shifts. Birth rates have fallen dramatically and immigration has plummeted. Who is going to live in all these new apartments? Over a hundred colleges close every year due to a lack of students. What happens to that real estate? Those don’t draw as much attention as my writing on AI but I think it’s just as important.

I generally aim to give people insights into what might happen 6 to 36 months from now. I’d love to speculate farther out as well but I don’t want to risk anyone calling me a futurist.

HW: Two of the companies you cofounder – General Assembly and Common – both were in areas post-funding saw the venture capital hype cycle take hold – from being in-fashion to less trendy. How much did those narrative swings impact the way you built the business, and ways it helped or hindered what you ultimately wanted to accomplish?

BH: They were very different. With General Assembly we nailed the timing. We started working on it in late 2009, just before learning how to code became sexy and every Fortune 500 B2C company needed to get digitally savvy. We sold in mid-2018 right before the pandemic and AI hit. 

But I’d say General Assembly’s concept was never particularly trendy among VCs. We believed having a brick-and-mortar presence was important, which scared many investors but ultimately allowed us to build a great enterprise business. Two of our last three rounds were led by family offices, which in hindsight enabled us to successfully exit when we did.

Common was a much tougher situation. The coliving concept got very trendy very quickly. Six to ten companies raised meaningful venture rounds, which led to a lot of competition and compressed margins. Ultimately we and many of our peers made bad economic choices in the name of grow-at-all-costs, and many of the decisions I make today at Thesis Driven are informed by mistakes I made at Common.

HW: Related to this question about venture capital, what advice do you give proptech founders about whether VC is the right source of investment capital for their business? 

BH: If they’re genuinely building technology, venture capital can be a great path. Vertical software is a great category for VC. There are also interesting data and marketplace opportunities in real estate that could likely have venture-scale outcomes.

The challenge is that there are a lot of asset management businesses out there that don’t have a good path to raising seed capital outside of venture. These businesses need to exist and can be great companies – asset management is an excellent business – but they usually don’t have the predictable, exponential growth arc that venture needs. If they raise VC, they usually get stuck and it’s a bad outcome for an otherwise good company.

HW: How much do you ‘bring your work home’ – with three kids have any of them shown similar interest in these areas? Is Thesis Driven multigenerational? 

BH: I’d love to build a multigenerational business, but the next generation has to want it. I won’t pressure anyone into it. Our oldest is nine, right now he wants to buy a farm and run a farm-to-table restaurant. He did have a very successful pie-baking business last Thanksgiving. We’ll lean into their interests, show them love, and see where it takes us.

Thanks Brad!

Spring Links! All personal blog posts today. No corporate (or even indie) media

Outcome Engineering [Cory Ondrejka] – “The code doesn’t love you back.” That’s one of the memorable lines in Cory’s manifesto around the changing nature of what it means to be an engineer. Importantly he doesn’t just rant but here coins what he believes we’re heading into: outcome engineering (o16g). Alongside the term are 16 principles, such as #4 The Backlog is Dead, #9 Agentic Coordination is New Org, and #16 Audit the Outcomes. I worked with Cory at Second Life and he later moved between other startups of his own creation and BigCos (having led the mobile app transformation at Facebook, and served as a technical advisor to Sundar at Google.

Opting Out of Unicorn Economics [Bethany Crystal] – It was a brilliantly catchy way to describe the data in the moment, but the whole concept of ‘unicorns’ in startup world (and striving to be one), helped break some part of our community. Or at least created a narrative that was surface-level easy to understand but with implications that were slower to play out. More builders are realizing the tradeoffs and publicly talking about why they’re eschewing the goal, often aided by the power of AI tooling (which of course is built by mega-unicorns ). Bethany, who has been on the inside at a top VC firm earlier in her career, now sits far from those aspirations.

“For a very long time, I believed the only way to start a company in the tech sector was to have an engineering degree and millions of dollars on your side. In other words, if you weren’t a unicorn chaser, you were just a small business owner. Or worse…a consultant.”

“When I started to notice that the most celebrated outcome in an industry of builders became check writers instead of company builders, something felt misaligned to me. After all, if the highest-status role is capital allocation, who is left to do the work of building?”

But also be wary of those folks selling solo founder plus AI equals the other model for success.

“But what do you notice about the people who are signing up for that program? All men. Most with engineering backgrounds. And so the lore lives on.

To be clear, I don’t think the answer is to replace one fantasy with another. It seems trite to trade unicorn chasing for solo founder worship, or to swap venture-backed pressure for an “AI for everything” grind dressed up as freedom.”

Knowing Bethany I can vouch that this essay is the outcome of choices she made – and is making – rather than just content marketing.

The Hidden Cost of Communication (A Case Against Big Companies) [Joe Fabisevich] – Joe published this right after the Block layoffs and I think was a little worried it would appear insensitive to the people who lost their jobs but it’s timely, accurate, and he seems to genuinely be a good human. In the post he makes the case that just about every company of significance is fundamentally overstaffed and that this results in lack of focus and underperformance from the communication complexity which occurs as a result. Joe doesn’t believe this is just an AI story – in terms of the need to rationalize team size – but that of course it’s now part of the consideration set.

“This is why the layoffs we’re seeing aren’t just about replacing workers with AI. They’re about companies finally accepting what was always inevitable — you don’t need 50,000 people to do the work of 30,000. You never did, but AI has made this reality impossible to ignore.”

Don’t Sell the Work [Evan Armstrong] – When your essay’s subtitle is “The most popular thesis in AI was wrong. Here’s why.,” I’m gonna lean in. And it just gets spicier from there.

“Unfortunately for all of us, this elegant idea turned out to be very wrong. There is exactly one category of startups where the model has been effective—AI customer service—and every other major AI application today uses a different positioning and pricing strategy.

So what happened? Why has “selling work” been such a dud?”

I’m not yet sure I totally agree with his framework, but as someone who is default skeptical of any single attempt (me sometimes included) to explain, create, and own the descriptions of tech transformation, this is a chewy complement.

Stop Being a “Maybe”: Emerging Manager VC Fundraising Advice on Qualifying LPs Like a Sales Funnel [Julia Maltby] – Oh thank goodness. I tell you, all these VCs have funding advice for their startups and then don’t take any of it to heart when raising their own funds. When backing EMs via Screendoor, our fund of funds, some folks are raising for the first time in their careers and the advice Julia provides here is pretty consistent with what I share.

“When you move from doing deals to raising a fund, you become the product. And like most products, you end up in a pipeline on someone else’s screen – color‑coded, half‑remembered, competing with a lot of other “pretty good” options.”

Enjoy your Sunday!

Tip DON’T LET AIRLINE RIP YOU OFF ESPECIALLY AS OIL PRICES CLIMB: I’m using Junova to track purchased airline tickets I’ve taking and auto-reclaim credit if the price drops. It was started by a friend and so far has recouped $2000+ of American and United credits for me. Their business model is: service is no cost, but if they successfully get you credit, they charge 20% of the value to your credit card. If you use this referral link, your first $25 of fees (ie $125 of flight credit) is free. Let me know how it works for you!

My Actual Savings This Year!!!

Automating a strategically sub-optimal process or workflow doesn’t make it markedly better. In some cases it’s even worse (eg a low converting marketing funnel can churn through your target list even faster if an agent is doing most of the work). And something that’s been automated – recently ‘improved’ – is even less likely to want to be revisited post-optimization. Human (and organizational) nature that you’re entrenching the process further vs re-examining it.

Each morning I hand in my too cool GenX card for a few minutes and go STRAIGHT BOOMER while using Facebook to wish my friends a Happy Birthday. That’s right Birthday Notifications Product Manager, I’m your 365 DAU. Some folks publish their ages while others have them hidden but quite often I’m surprised by how young most people still are – in the sense that maybe we met while they were just out of school or in their first job, and this was 10-15 years ago, so they’re early 30s or whatever in 2026. For context, I’m 52 and have been out in Bay Area since 1998 — many of the folks in my network were born later, the Millennial cohort especially over-represented on Facebook I’d imagine.

It also occurs to me that something different might be happening on the other end of the connection: the Birthday celebrant feeling they are so old. My own projection? Possibly. I’ve written before about my 20s and 30s trying to outrun a ‘failure tiger‘ and then in my 40s coming to grips with moving into an ‘elder’ statesman tier. But conversations among ourselves suggest this cycle repeats itself every generation. Plus the hastening pace of both signal and noise within the AI supercycle has its own exhaustion (exasperation?) for many.

Rarely does it help to tell someone they shouldn’t feel the way they do, so dismissing their ‘I’m getting so old’ without recognizing the power of those thoughts would be ineffective, despite the bluntness of this post’s title. Instead I’ll just reiterate what I said in the first paragraph: the “HBD ” poke you see from me isn’t just a ‘way to go’ but it’s a ‘you’ve got a ways to go.’ Lots done already and lots more time, energy, and cycles ahead.

Got to meet Dan Teran when we backed his NYC-startup ManagedByQ, in the office management vertical. Now more than a decade later he’s a frequent co-investor with us, having started his own venture firm Gutter. Seemed like a good moment to check in and ask Five Questions.

Hunter Walk: Give us the quick overview of Gutter Capital with particular emphasis on completing the statement “unlike other early stage venture firms Gutter…..”

Dan Teran: Unlike other early stage firms, we roll up our sleeves and build alongside our founders. We combine our experience as founders and operators with a concentrated strategy (5-6 investments per year), which gives us time to work directly with founders at a depth that is unmatched by other firms. In addition to coaching and mentorship, we embed our operating partners (Richard and Vince) directly within the portfolio as player-coaches to help solve the most important problems.

We are also unique in that we choose to work in person, alongside our founders.  At Gutter HQ on Canal Street in New York City, we have over 70 founders and operators across 12 companies ranging from pre-seed to Series B working side by side. It is a special environment to build a company in, and a huge draw for talent. To reinforce the spirit of community at Gutter, we share 5% of the GP carry from each fund back to the founders, so everyone has a real incentive to help each other.

HW: You were CEO/cofounder of ManagedByQ, an early software+services company in the proptech space. Successful exit but tough market. Would today’s tooling (AI in particular) fundamentally change how you would have built that company in 2025 vs 10 years earlier? Knowing what you know now, would you have started that company? Would it have passed Gutter’s funding screen?

DT: Managed by Q would definitely be a lot easier to build today than it was in 2014, both in terms of the speed of building traditional software and the experiences that LLMs can facilitate.  The problem at the core of office management is routing a bunch of requests from internal stakeholders to a network of external vendors. I think an AI agent would be well suited to this task.  

Having said that, it’s not a company that I’d start today.  My bar for working on meaningful problems has gone up since I was 24, and while there are aspects of managing physical spaces that I still find interesting, it is not a problem space I’d be eager to dedicate my life to (again).  I also don’t have a strong view on the growth of the office as a market, which would make it tough to get excited about.

HW: Gutter focuses a lot on helping its founders build out their team. What does the talent landscape for startups look like in 2026 and what do you tell CEOs about strategies for retaining their best team members (who are getting recruited every day by their friends/competitors)?

DT: The talent market today looks surprisingly like it did in the go-go days of 2021.  The competition for experienced technical talent is as fierce as I’ve seen it in the past 15-years, which makes sense given the extreme leverage that code generation tools unlock.  Even the competition for sales talent remains as competitive as I’ve seen it.  

We have been fortunate to have <5% regrettable attrition across the 100+ individuals we’ve hired into the Gutter portfolio. I would attribute our unusually high retention to two things.  First, we are judicious in screening for candidate-stage fit.  In our experience, most mistakes in early stage hiring result from people not understanding the expectations of an early stage company.  Second, our founders are working in service of inspiring missions. When you can articulate to someone why their work matters and pair that with a high agency environment, you have a recipe for long term retention and dedication. 

HW: Which aspect of Gutter’s investment process has become more data-driven/automated over its lifetime? Something that before needed to be done manually or where you might have previously incorrectly thought human ‘touch’ was necessary/optimal?

DT: We maintain a very manual investment process, largely out of respect for founders and reverence for the difficulty of the job.  Early stage investment decisions contain a tremendous amount of nuance, which AI is not well suited to manage today.  We have built an internal AI tool that helps us to manage the diligence process, but it mostly helps us to see what we are missing and direct further diligence rather than replace human judgement.

We have also built some AI tooling to manage the large volume of inbound pitches that we receive. We hold ourselves to a high bar of responding to thoughtful, personalized pitches with thoughtful, personalized responses…but we also receive a lot of AI slop. Regardless of quality, we aim to respond to all inbound pitches with detailed feedback or targeted requests for more information within 72-hours.

Personally, I am most excited about the application of AI post-investment.  Over the past few months we’ve built the GutterOS, which helps us track portfolio support activities post investment and evaluate their efficacy.  This allows us to focus limited resources on the highest leverage opportunities, and proactively surfaces gaps in our portfolio support capabilities.

HW: Who is someone outside of the technology industry that influences how you understand the future?

DT: Recently, Barbara Tuchman’s Guns of August has been weighing heavily on my mind.  She paints a vivid picture how weak leaders, poor judgement, and inflexible institutions led the world to war in 1914. Events take on a life of their own.  The venture capital community’s new found obsession with defense contracting makes me very nervous. To paraphrase Chekhov, if a gun appears in the first act, it is going off by the third.

Thanks Dan!

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