2026-05-10 05:29:44
Happy May! Happy URLs!
When Your VC Leaves, You Are Fundraising Again [Oana Olteanu/MotiveForce] – “You are likely screwed if I leave my venture firm,” is, not surprisingly, among the most popular topics that our industry chooses to content market around. But these transitions are increasingly common, which caused me to write “Oh Shit, Your VC Just Quit Her Fund! What a Good CEO Should Do Next.” in 2019. Oana provides her own perspectives on how founders should react to circumstances like these – there’s a lot of consensus between the two posts so read them both!
How American Dads Became the Parents Their Fathers Never Were [Derek Thompson] – My joke about the post-economic version of the ‘American Dream’ is that our children go to therapy for something less significant than we do! Being a great dad is a centering priority in my life. It doesn’t necessarily occur to the detriment of other pursuits but certainly if it had to, well, I’d make the tradeoff for my daughter. The ‘rise in fathering’ as it’s called here, can be tied to a number of societal developments, and while still most pronounced amongst high-education cohorts, the trend line is consistent regardless of degree status. Thompson theories that it’s not just driven by touchy-feely love for your kid, but also the ‘keeping up’ fear – spending time with your child to drive them to the performance levels that the future will require for school, economic stability, and so on. And perhaps spending more time with your family results in less socialization generally, which also can be tied to a host of ills, especially once your child is out of the house.
The Camel, the Straws, and the Bagel Shop [Darcy Burner/Burnery] – The subtitle on this one is “Why progressives need to be honest about what their policies cost small businesses, and strip out every cost that doesn’t serve a progressive value.” PRAISE THE LORD! Darcy, a former SMB manufacturing owner, claims when “progressives talk about small business failures, there is a tendency to treat each failure as an individual story of personal responsibility while ignoring the environment those businesses are operating in.” And advocates for reforming the unnecessary – or least important – ‘straws’ which can break the camel’s back.
“If you’re going to load the camel (and you are, and some of those loads are worth carrying) then you owe it to the camel to take off every ounce of weight that doesn’t need to be there.”
Some Thoughts on Employee Stock Options in 2026 [Bijan Sabet] – Spark Capital’s cofounder [stepped away a few years ago; did a term as US Ambassador to Czech Republic] looks at the state of startup employee equity in 2026 and suggests two things are true: companies should be more transparent around all the factors that can let a team member assess value [not just ‘number of shares’] and early folks need more stock. Agreed – in 2017 I suggested Founders Should Set Aside More Equity for Their Team & “Split the Pain” With Investors. My lived experience right now is it’s pretty split – some founders go by standard benchmarks and ‘best practices’ while others use compensation plans as ways to set their culture. For example, giving all early engineers the same generous equity regardless of seniority level [these aren’t exec level hires so more among 2-5 years of experience].
‘They Said A.I. Saved Me’: How South Korea Is Checking on Its Seniors [Choe Sang-Hun/New York Times] – As someone deep in ‘sandwich generation’ complexity it’s exciting to see other countries embracing technology as a productive tool to assist their elderly population. This absolutely going to be an important area of development – not dystopian and deserving of public research/funding in addition to private markets. Everything from wellness checks, to cognitive exercises, to plain ole companionship.
“The bot has become a genuine helper, flagging hundreds of emergencies. In one instance, social workers said, it reached a woman with mild dementia who had wandered off and lost her bearings; she answered the bot’s scheduled call, allowing officials to locate her.
To prevent scammers from mimicking the service with a human voice, the bot intentionally sounds slightly mechanical. For Park Jong-yeol, an 81-year-old Vietnam War veteran, none of that matters. The bot, he said, is “better than a human.””
Enjoy your weekend!
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 [update: WHICH I’VE SUCCESSFULLY APPLIED TO FUTURE TICKETS!!!]. 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!
2026-04-19 00:47:39
LinkedIn could save most VCs a step by adding a post template called “AI Dinner.” You upload a picture of the full table and a picture of the custom menu card with your firm’s logo on it. Then it pre-fills the text of “Still buzzing from bringing together all these AI Builders last night,” while also auto-tagging the attendees. Magic!
Snark aside, I do think it’s wonderful that people are spending more time together and supporting local businesses. But it’s clear that many of the hosts are first-time event planners so here are some of my suggestions, guidelines and rules.
What am I forgetting?
2026-04-18 02:05:41
Was talking with a fellow VC the other day who had just decided, after substantial deliberation, not to invest in a startup he was evaluating. “I hope I’m right [to pass],” was his comment, reflecting the uncertainty in his mind.
“Really? I hope you’re wrong,” was my reply.
Not because I’m an asshole (that’s besides the point), but instead it’s so much more fun to root for a team’s success regardless of whether or not you’ve backed them. The number of founders who I truly am excited about as people is so much greater than total investments we make each year (~15) — we leave many pitch meetings honestly hoping they build something meaningful, regardless of whether we’re able to participate in that outcome.
We’re investing our own personal capital in Homebrew IV so when we do commit to a company, it’s as close to literal skin in the game as you can get without being on the org chart. But regardless, false negatives in decision making is definitely part of being in venture. As I’ve found, if you haven’t passed on some billion dollar companies you probably haven’t backed any either. Homebrew has invested in a bunch, passed on an equal or great amount, and even lost several in competitive situations.
I wonder how transparent this is to founders? When they hear a ‘hey, we’re not going to participate in this round’ can they tell whether the investor is still rooting for them or not. Is the offer to ‘help if we can anyways’ sincere or not? How many of us actually ‘root’ from the sidelines versus just say it?
2026-04-02 03:14:44
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!
2026-03-30 03:18:30
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.
2026-03-26 05:50:19
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.