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!

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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!

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!