Strava's AI just told me I crushed the NYCRUNS half marathon in Brooklyn with my 1:35. It said I “sustained high intensity throughout with impressive heart rate effort.” I got similar feedback when I ran the NYRR NYC Half.

Not true.

In reality I’m in a slow recovery from from a torn proximal hamstring tendon and I haven’t been able to pinpoint why I just wasn’t running at the speeds I wanted to, despite feeling like I’m in good shape. It felt like I had another gear that I just wasn’t able to shift into.

I took my Strava data from these races, along with peak previous performances on the same course, and uploaded it to Claude with the following prompt:

“I would like you to compare two sets of races on the same course... the Brooklyn Half and the NYC Half. 2026 times are after a torn tendon (ischial tuberosity). Is there any insight you have into what's hindering me in this post-tear recovery?”

A minute later, I had charts, insights and the ability to query it further.

Writing a book demands something different from you than a blog post ever will. When someone pays for your work, you owe them something. You have to think about the full scope of what they need, not just what you feel like complaining about that day. You become accountable. And that accountability forces empathy.

Doing some customer empathy exercises is critical to any successful career. When you write a book, for example, you are forced to think about scope. If someone is going to pay for this, how do I make sure I don't leave them with unanswered questions?

The writing process also trains you in a specific way. Once you're in "sharing mode," you become hyper observant. Every conversation with a founder became research for me. I noticed the questions people actually ask, the confusions they have, the gaps in what's out there.

Training that observational muscle makes you better at everything else you do.

f you're a consumer founder who's gotten passed on by investor after investor, you've probably been told some version of "You're a little too early for us"—or you've assumed that most VCs just don't understand consumer. There's some truth in that—but mostly if you’re pitching the wrong investors.

It's not the whole story, and honestly, stopping there doesn't help you. The struggle runs deeper. It starts before you ever send a pitch deck.

I backed a micro-mobility company about six or seven years ago. The company was run by a Hispanic founder. He was gritty, insightful, and every bit as hardworking as anyone I've ever funded. Yet, he struggled to raise. Ultimately, the company went under. Not having enough capital to push product innovation was the biggest issue.

I saw that Joseph Cohen had raised $14.2 million in total for Infinite Machine, with investors including a16z's American Dynamism fund. They’re building what can reasonably be described as Tesla for ebikes. They literally look like a pregnant Cybertruck gave birth to an ebike. I’m told it’s really fun to ride and as a big fan of the Revel scooters, I believe it.

If you’re looking at the two companies, the easy read is: bias. Hispanic immigrant founder couldn't raise, connected white guy from Penn clears double digit millions.

Case closed, right?

I thought it was an interesting example by which to dig deeper into the nature of how bias and capital access works.

I've been doing a lot of talks with students and founders related to my new book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded which is now available for pre-order. (If you enjoy my writing here, please consider buying it now. If you e-mail the receipt to founderunfriendly@next.nyc, I’ll invite you to this amazing AMA series we have with founders from Datadog, Brigit, Zerohash and more…)

Here's how the post-talk networking usually goes: a minority of the people follow up with a LinkedIn invitation, and that's pretty much going to be it. They'll never follow up again. Ten years from now, either one of us will notice the other as a potentially important connection that seems valuable, but we have no idea how we're connected.

That's not a relationship. That's network lint that just gets in the way of a search to find a useful bridge to someone.

There’s a better way to establish yourself as a three-dimensional, memorable professional that adds value and offers a connection from a position of strength, no matter how down the ladder you feel.

Every emerging manager gets asked the same question eventually, usually by an LP who has seen too many pitch decks: “Why do you exist, and what are you genuinely better at than everyone else?”

A thesis and a network are table stakes. Everyone has those. And in a world where founders can get further on less capital than ever before, and where the number of funds multiplied wildly a few years ago, table stakes aren't going to hold up much longer.

The funds that are going to matter are the ones that have built something irreplaceable beyond the checkbook.

You’re sitting in a board meeting watching your CEO paint a picture of the next 18 months, and everything they’re saying is…

…not impossible, but...

But you know the assumptions underneath it. And you’re about to have to present the model that’s supposed to back all of it up.

That tension — between what’s possible and what’s probable — is the part of the job you feel your reputation is tied to. Not the spreadsheet. Not the close. The job is being the source of truth in a room that has strong structural incentives to prefer the optimistic read is what causes you the most anxiety.

In 2010, Facebook launched Places. It was their answer to Foursquare.

It failed almost immediately—not because the feature was bad.

The graph was wrong.

When people built their Foursquare networks, they did it knowing exactly what the app was for. A Foursquare friend request meant something very specific: You’d be ok running into this person IRL. Facebook's graph was built for something else entirely—reconnecting with classmates, staying in touch with family, documenting life milestones. By the time Facebook tried to bolt location sharing onto that, nobody wanted to tell their grandmother where they were having drinks on a Tuesday.

The graph had no context. It failed.

One of the best pieces of fundraising advice I ever gave — and honestly didn't fully appreciate until I said it out loud — came out of a conversation I was having with Lauren Pearl, a CFO advisor who works with a lot of early-stage founders on bias in fundraising.

Specifically, the well-documented phenomenon where female founders get asked disproportionately more risk-focused questions than their male counterparts. The HBR study on this is worth reading. The basic finding: investors ask women "prevention" questions — what could go wrong, how do you protect against downside — and men "promotion" questions — what's the opportunity, how big can this get.

Lauren was making the point that founders who face this kind of bias need to be extra prepared. Have the numbers buttoned up. Be ready to defend the model. Know every assumption. I agree with all of that, up to a point.

Here's where I pushed back: Don't answer the question.

Most of us quietly curate our invitation lists to protect ourselves from the sting of low attendance. We tend not to ask hard questions of people we know won’t go easy on us. We stick to friendlies and narrow the ask to control the outcome. We'd rather invite 10 people and have 8 show up than invite 100 people and have 30 show up — even though the second scenario is objectively better as an outcome (unless you’re an introvert, of course).

The founders who fundraise well tend to have this same quality. They can send 200 cold emails, hear back from 12, meet with 6, and move on without a crisis. They're not deluded — they know most people will say no. They just don't let the no's accumulate into a story about themselves.

If you got passed on and you're blaming the cap table, I want to push back on that.

I recently hosted a webinar with Qapita, my favorite cap table management software and nextNYC sponsor, with Holly Neiweem, Managing Partner of Apprentice Ventures, and Colin Kirby, who heads the emerging companies and venture capital practice at Foley Hoag. Between them, they've seen it all — 90-investor cap tables, departed co-founders sitting on 40% fully vested, angel investors still on boards three rounds later with no follow-on check to show for it. And their message was consistent: a messy cap table is almost never the actual reason a deal doesn't get done.

If you’re a junior investor right now, none of this is surprising. You’ve felt it. You send the email and it goes unanswered. You get the meeting, but the founder is clearly waiting for your partner to join, or even explicitly asks. You make the intro internally and someone senior takes over. You’re working hard for the firm, but it’s not clear that your long term value as an investor is accruing. 

Are you actually gaining “juice”, or just renting someone else’s?

Sixteen years ago, I wrote that, “Business plan competitions are the air guitar championships of the startup world.”

I meant that you can mimic all the movements of a startup without any of the real risk-taking or building. My criticism then was that we were teaching students to pitch without teaching them to build.

Fifteen years later, that gap matters even more. In a world where AI can help anyone ship a working product in a weekend, and where entry-level jobs are disappearing, the ability to actually build something—even something small—isn't just a nice skill to have.

It might be the whole ballgame—and I’m curious how many universities are thinking this way about their entrepreneurship programs

There’s an assumption founders make about hiring part time roles. At some point, when we can afford it, we’ll stop patching things together and hire the real person. We’ll commit to the singular owner. We’ll professionalize the function.

Fractional or modular support is what you do before you’re serious or successful.

I see this mistake everywhere. A founder hires one early marketing leader and expects them to own brand, demand gen, content, performance, product marketing, analytics, and team building.

It works for a while when you’re growing off a small base. Having someone do a smattering of things is better than having no one on it.

Then the job changes when you need focus and specialization to move the needle.

The skill set that got you from zero to traction isn’t the same skill set that scales paid acquisition, builds a content engine, or manages a team of specialists. Suddenly the first hire isn’t wrong. The role has outgrown the shape it started in.

There’s been a pretty common belief in the venture and startup world that is changing:

If an employee wants to sell shares, they’re probably thinking about leaving.

If a founder takes some money off the table, they’re losing faith or they’re going to take their foot off the gas now that they’ve got some money.

I think VCs and founders are getting increasingly convinced this framing is off.

A lot of my coaching clients have the goal of becoming a Principal or Partner someday. I almost never start by talking about titles. Instead, I ask a different question: three to five years from now, what kind of founders will already want to talk to you before you ever reach out? Not because of where you work or what’s in your bio, but because when they look at your background, they immediately recognize shared experience or unusually deep understanding of a problem they’re actively wrestling with. If you can’t answer that question clearly, the path to becoming a great investor is still mostly theoretical.

I’ve joined Intro and I’m donating the first $2,000 of my Intro proceeds directly to the National Brain Tumor Society in memory of my parents. Both of my parents ultimately passed from brain tumors–my mom six years ago when an otherwise operable brain tumor was complicated by a long struggle with COPD and my dad from CNS Lymphoma a year ago.

I wouldn’t be who I am today if it wasn’t for them–and so making more time for founders and tech community professionals, and raising money in their honor, seems like a fitting way to kick things off with Intro.

I’ve spent most of my adult life on social media.

I was early to blogging, Friendster, MySpace, LinkedIn, Twitter, Foursquare, etc.

I’ve written newsletters, run communities, hosted events, and watched every generation of “this is the new way to connect” rise and fall. I’m not anti–social media by any means—but over time, I’m lamenting how anti-social it’s all become. I don’t have Threads friends the way I used to have Twitter friends—and in an algorithmically driven experience, following doesn’t really mean I get to see what the people I care about post anymore.

Finally, I found something that feels like the next social network for me.

E-mail.

One pattern I see over and over is that female and underrepresented founders tend to be extremely conscientious in how they answer questions. They take each one seriously. They assume it deserves a direct, precise, fully reasoned response.

That instinct makes sense.

There’s a real power dynamic at play. Capital feels scarce. Access feels fragile. And if you don’t often feel like you’re in the driver’s seat in rooms like this, the natural reaction is to respond exactly as asked—carefully, thoroughly, and defensively.

The problem is that if you do this for the entire pitch, the conversation slowly drifts away from the most important thing: why this company could be big.

Moving from one VC firm to another is not a simple job search.

It doesn’t behave like one. It doesn’t follow job-search timelines. And it doesn’t reward job-search behavior.

Firm-to-firm moves are slow by design, because the candidate pool already exists—at least at the senior level. You’re unlikely to get a senior level or partner track position in venture if you don’t already have some investing experience—and that’s a finite pool. Narrow it down to a specific sector and they already know dozens of plausible candidates.

They’ve looked at deals together or competed head-to-head.

It’s extremely unlikely they’re going to ignore all of that context and hire someone simply because that person decides it’s time to look.

Which means the real starting point isn’t who’s hiring.

It’s who already knows you, and what they think of you.