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.

1. Prompt schedule and clear timing. First 30 minutes are for drinks and mingling, then we sit. Try to get dinner done in 90 minutes. Two hours on a weeknight is fine.
2. Name tags and/or table cards please.
3. After entrees, accommodate some people needing to leave and let people switch seats to maximize conversations. These actually pair well together because you can fill in empty seat holes easily from no-shows and exits.
4. Attendee lists. Sending out before is tricky because you might still be trying to confirm some folks, deal with last minute cancelations and generally prevent guests from pre-judging based on who may/may not be there. But I do think afterwards it’s great to send out names and email contact info for everyone who did make it.
5. Moderated/guided conversations. It’s really challenging in large groups to have “one conversation.” Single tables of up to six can do it – larger than that and you tend to break down. You can have multiple tables all starting with the same prompt, but avoid the ‘report out’ unless it’s really easy. This isn’t a class seminar and it’s not a TED talk.
6. Sponsors. I understand you might have them and it’s ok to acknowledge them. If they’re pitching, 30-60 seconds is really all they should need. And make follow-up with them opt-in vs opt-out. I don’t need three notes from someone trying to sell me something after the dinner just because they helped pay for my meal. This isn’t a timeshare pitch.

What am I forgetting?

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?

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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