Five Great Blog Posts I Found This Week

Tough Love, Running Effective Meetings, Making Products That Produce Emotion, and More

Cross-country flights are great times to catch up on newsletters and unread feeds. This week there’s a bunch I want to share with you.

  1. How Levels Does Meetings

Levels is a consumer health company focused on glucose monitoring and they run themselves in a very deliberate manner, mostly asynchronous and fully remote from what I understand. Levels publishes a lot of how they work and the above meeting guide is a great overview of system-thinking. Not all of it will necessarily be the right fit for your org, but it’ll certainly produce some ideas

2. Tough Love by Jared Hecht (Fundera and GroupMe cofounder)

Jared’s a really talented NYC entrepreneur who recently started blogging more. ‘Tough Love’ is about being good at giving hard feedback, especially as an investor. As Jared notes,

“The irony is that withholding the truth is the opposite of being founder friendly. There is a market for those who can do this exceptionally well. It’s something I try to do when I invest in companies and work with founders. And to my delight, it’s not just me who appreciates “real-talk.” Entrepreneurs crave it. They may hate it in the moment because it can hurt the ego, but it resonates. When it comes to company building, I want to partner with someone who tells it how it is and isn’t afraid to hurt my feelings than someone who prioritizes simply being liked. In my experience it’s those that dish out the tough love that I’ve grown closest to and admire most.”

Read the whole post and subscribe to his newsletter.

3. Optimism Shapes Reality by CEO/cofounder Alexandr Wang

One of the advantages working at a high quality company provides is understanding what excellent execution really feels like. In this post Alexandr talks about when he felt that first within, how he communicated it to the team, and his philosophy on maintaining it. Not so much with org charts and KPIs, but with goal setting and optimism.

4. Optimizing For Feelings by The Browser Company

An incredibly sharp team that’s doing what the company name suggests: building a modern web browser. Ambitious, yes? The team comes from a ton of different web2 successes (and beyond), and they’ve eschewed a number of the traditional ways of measuring product success. Not just shooting for numerical targets as a true north but rather vibes. It’s one of the things I was getting at a few years back in my own post, We’re Running Web 2018 With Web 2008 Dashboards. And That’s a Problem, so I’m of course down with what they’re trying. And also a personal investor, so skin in the game.

5. Applying the Burn Multiple to Marketplace Business Models by Jeff Fluhr (Craft Ventures)

Jeff modifies his partner David Sachs’ SaaS ‘Burn Multiple’ concept for marketplace businesses. I find these types of analysis really compelling and it forces you to justify why you’re a positive outlier if you aren’t tracking against their segmentation. That’s not to say that it’s 100% correct but it’s certainly directionally right. And Jeff just led a deal we participated in, so I’m excited to hopefully see this play out in that company.

There you go, five of the best things I read on airplanes this week 🙂

15,000 Tech Workers Have Been Let Go In May. Were You One of Them?

The Things to Know When You Lose Your Job In A Downturn

RIF aka reduction in force. Sounds like a Magic: The Gathering card but it’s actually a polite way of saying you’re being laid off. And with the tech valuation reckoning underway, if you’ve been RIF’ed you’re not alone. I can’t tell you whether this is just a few months of rightsizing or a multiyear recession but I do anticipate there are going to be more cuts — and outright failed startups — before our industry outlook returns to half-full instead of half-empty. In these moments there tends to be a lot of content to help CEOs and founders manage through a downturn, but not as much for those team members impacted. So let me take a (non-exhaustive) cut at Things You Should Know If You’ve Been RIF’ed….

NO SHAME. For many people this will have been the first time you ever got let go, and the emotions can be fierce. Know that many of us (myself included) have been in similar situations, and you shouldn’t feel embarrassed. It’s not the end of your career, your reputation has not be sullied, and there are still seats on rocketships waiting for you.

The Blocking and Tackling Basics of What to Do When You Lose Your Job. Our Head of Talent Beth Scheer wrote this resource as an overview of things to consider as you’re exiting a company. Not every situation will apply to each individual but folks have found it very helpful and comprehensive. If you have any questions about its contents or any ideas for things we should add, tweet at Beth.

Some Things You Can Ask For On The Way Out That You Didn’t Know You Could Ask For:

  •           Rewrite Your Job Title

Very often at startups your title isn’t reflective of all of your roles, or is quite generic. This is great for company culture (in my opinion. I agree with Gokul.) but it’s not as helpful when you’re suddenly looking for a job. Sometimes, within reason, for the sake of specificity and focus (not aggrandizement) the CEO/your manager at your former startup will allow you to change your outgoing title, so that when you apply for new jobs, it better fits with what you’re seeking in the role. For example, I was sort of a non-engineer jack of all trades when I worked at Linden Lab (makers of virtual world, err metaverse, Second Life). When I left in 2003 we agreed that my final title could be focused on Product and Marketing, since that’s what I was interested in pursuing next. Obviously this can be a bit tricky but in small companies when you have kind founders and you’ve been a great team member, it’s ok to ask.

  •           Extend Your Stock Option Exercise Period

The ‘average’ startup offers a 90 day period post employment where you have to exercise any vested stock options before forfeiting them back to the company. An increasing number of companies have created more flexible timelines and in the wake of non-performance based layoffs, can sometimes change the structure for terminated employees. There are tax implications, etc etc and IANAL (or accountant) but be sure to check your stockholder agreement and ask your HR person about this.

  •           Prep your manager, peers to be references. Perhaps even ask founder/CEO for a favor chit.

Basically replenish your reference checks. Don’t script their answers for them, but keep them in the loop about what jobs you might be seeking out next, how you’re describing yourself, and so on. If you have a relationship with the CEO or another VP/C-level exec at your previous company, you might let them know that you might need their help. Basically, if there’s a job you’re applying for where you’re getting deep in the process, a note from a previous CEO or executive validating that you’re awesome, that you just got caught up in some hard decisions they had to make as a company, and that they’d hire you again in a new venture, is going to be a pretty strong thumb on the scale.

And finally, two conversations to have with yourself

Even if the job didn’t work out exactly the way you hoped, was joining the company the right decision? If you can focus on making the right decision repeatedly, you’ll be quite successful over time, even if some of the outcomes aren’t perfect. Understand your own framework for decision making and keep it honed for the next choice you’re going to make. Which is…

What do you want to optimize for next? I don’t believe you can start a job search without knowing what’s most important to you. It’s not about pros and cons, but tradeoffs. Figure out what 2–3 qualities matter most to you for the next phase.

Whether you’re heading right back into the job market or taking a break, Homebrew portfolio companies are eager to talk to you when you’re ready!

“My career was on the rise, I had the beginnings of a financial safety net …Yet I started to suffer from debilitating panic attacks”

Andy Johns Was In-Demand As a Startup Growth Guru But Couldn’t Continue The Work Until He Helped Himself First

Andy Johns was one of the original notable ‘growth’ experts, working at a variety of startups and larger tech companies to help drive product strategies that resulted in organic and sustainable user acquisition. We were fortunate to include him as an advisor to our portfolio during early Homebrew investments, and he eventually crossed over to venture himself, before stepping back to focus on his own health. It’s that effort I wanted to focus on in this Five Questions interview. Thanks Andy for being open about your own diagnosis and subsequent healing.

Hunter Walk: Thanks for doing this interview Andy. We’ve known each other for a while and I wanted to focus today primarily on your recent writings about your personal journey to find mental health and wellness. What prompted you to start talking more publicly?

Andy Johns: My mental health journey first started in early 2010. Life was good at the time. My career was on the rise, I had the beginnings of a financial safety net, I was physically healthy and active, and I had a great group of friends. Yet I started to suffer from debilitating panic attacks, nightmares, depression, and an overall sense of feeling “out of control” in terms of my own mind and mood. It scared me enough that I feared my life was at risk so I began to reach out to therapists for help.

I’ve gone through several periods of focused mental health work, largely motivated by additional ups and downs that I’ve experienced since then. In the last 3–5 years I was able to process parts of my childhood trauma that contributed to the downward spiral that struck me in my late 20s. That involved many sessions of EMDR, a few intense but transformative psychedelic-assisted psychotherapy experiences, as well as over a month in a trauma recovery center where I worked 24/7 on my mental health.

As difficult as all of that work has been, it’s given me a new life to look forward to.

Due to the changes I’ve experienced, and the incredible people I’ve met along the way that similarly struggle with mental illness, the broad field of mental health has become a passion of mine. That’s what led me to start speaking publicly about mental health. Writing is not only a part of my wellness routine, and something that keeps me on track and accountable to maintaining my own health, it’s allowed me to connect in new ways with the technology community. Fewer of my conversations today are about startups and how to growth them. They’ve been replaced by deeper, closer conversations with people about the challenges they face in life and what they can do to find more peace and balance.

HW: This is an area that’s quickly destigmatizing, at least within the tech community. Have you found the same? Or am I just seeing what I want to see, given my own forthrightness about being in therapy too?

AJ: I would agree with you. On the whole, the technology community is more open about discussing mental health than most industries. The forward-thinking and open-minded characteristics common in the silicon valley have contributed to a broad awareness and acceptance of mental illness relative to most other places I’ve lived. That’s an attribute of the tech industry that I appreciate.

Yet I’ve also experienced a passive negative response in a few cases from a few people. And I know others that have lost career or business opportunities because potential partners in a deal were weary about working with someone that has a diagnosed mental illness. At an individual level, there remains plenty of narrow-mindedness amongst some.

That’s part of why I’m writing about mental health publicly. I don’t feel like I have anything left to prove professionally. I’m at peace with the work that I’ve done and the impact that I’ve had. I don’t crave millions of dollars or notoriety like the younger me used to. I have nothing to lose so it feels not only like a life calling but also a moral imperative. All I want for myself is inner calm, connection with others, my health, and to be fully aligned emotionally, mentally, and spiritually around a cause that gives my life purpose.

That said, what I want to do at this point is help others awaken from the trauma and conditioning of their past, and to free themselves from the perceived constrains of their present condition. I want to help others become free in the way that I have.

HW: How do you decide what to share, versus what’s more personal? For me it’s less about the content and more about the motivation. I really don’t want to write up stuff that feels like I’m being performative or manicuring something into a public narrative that’s not exactly true.

AJ: I feel the same way. If it’s inauthentic, I feel an internal disgust that won’t let me proceed since it knows that I’m being false. It’s as if the inner child in me is saying, “Listen, asshole. You’ve spent enough time living with this facade. Drop it and be real.”

When I write, I think about two first principles:

  •           Reasonable vulnerability
  •           Emphasis on healing

What I mean by “reasonable vulnerability” is that I want to share but do so with appropriate boundaries in place. My audience doesn’t need to hear every single detail in order to understand the concepts I’m sharing or to derive value from it. On the flip side, if I’m not vulnerable at al,l then the article may come across as generic and inauthentic. That’s the last thing I want. I don’t want to write a generic Buzzfeed-like article on “The Top 8 Ways to Start Meditating”.

However, it requires that I do share enough of my personal insights and experiences in order for it to be clearly authentic. That’s why I also have principle #2 of “emphasis on healing”.

I write because I want to help myself and others heal. In order for someone to be ready to heal, they must first feel safe. You don’t teach a dog a new trick when it’s shivering and has it’s tail between its legs. You teach a dog a new trick when it is calm, focused, and safe.

The same is true for people. As a result, I think of sharing my personal stories and insights as a way to make my reader feel safe. If they know that I’m being open, honest, and real, they’ll feel safe. I think that’s one of the reasons that I’ve had so many people in tech reach out to me to talk about their own mental health challenges — they get the sense that they’ll be safe when they talk to me.

So, when I sit down to write a piece, I always have that in the back of my mind. I ask myself, “What can I write that demonstrates reasonable vulnerability and is written in a style that emphasizes healing.” Then, when I’m hit by a sudden motivation to write on a particular topic, I combine that with my two principles and I let the words flow.

HW: Besides continuing to make sure you dedicate time to this, are there certain types of work you now want to avoid? Or types of personalities/situations that are especially triggering for you?

AJ: Yes, there are very clear boundaries in place for me at this point. I recently wrote about the concept of an “acceptable range of tolerance” in this substack post about knowing when to stop and take a break from work.

It’s a well-established concept in biology that states that life will either flourish or struggle depending on a collection of factors, such as temperature, and that life seeks the optimal conditions for thriving wherever possible. This same concept applies to people. There are ideal conditions in which the body and mind can thrive. And there are conditions in which both will suffer.

An important point is that the conditions that are ideal or suboptimal for me won’t necessarily be the same for everyone else. We’re all unique biologically, neurochemically, physiologically, and so on. As a result, the conditions we define for optimal performance must be custom-tailored to the individual.

I’ve learned that there are a few things that are essential for me at this stage in my life:

  1.           I won’t work for or with assholes. I’ve had enough experiences with bullying growing up to know that it creates a lot of internal emotional disharmony. And I still have work to do regarding my ability to set boundaries with authority figures in particular. I quickly fall outside of my range of tolerance when around aggressive people with sharp elbows.
  2.           I work less and make less money in exchange for a quieter, more balanced schedule. I will not allow myself to do more than 20–30hrs per week of work. That will force me to maintain plenty of time for self-care while also forcing me to work smarter rather than harder.
  3.           I must maintain a daily schedule of wellness activities. If I don’t, my nervous system quickly drops back into a default stage of alert agitation (this stems from having Complex PTSD). That involves exercise, hot sauna and cold shower/bath whenever possible, walks outside when the weather is great, waking up early and going to bed early, and making sure I have a clean diet and take my psychiatric medications. If I do, I’m much more resilient when I face adversity.
  4.           I also focus on “heart-centered” work instead of “head-centered” work. What I mean by that is I have a boundary around doing work that purely comes from an intellectual place. For example, much of the work I did earlier in my career was motivated by making money and gaining notoriety. That’s fulfilling to my ego but not my spirit. Now I’m focused on heart-centered work that satisfies my spirit — the inner voice that knows what is fulfilling for me. If I find myself falling back into old patterns of working on projects because of financial gain as the prime motivator, then I know I’m pursuing work from ego as opposed to work from a place of love and compassion.

HW: What are some resources that you’d recommend to folks who want to start thinking more about their mental health — like the 101 foundational stuff?

AJ: I have a complete list of my favorite mental health and spirituality content here. It’s a public Notion document that anyone can access.

In terms of foundational sources, I have a few recommendations:

  •           This interview with Dr Gabor Mate covers the relationship between childhood experiences and how we present ourselves to the world as adults. He is a true master of his craft and covers complex subjects with utmost clarity and compassion.
  •           The Body Keeps the Score is my favorite book on mental health and how to heal from trauma. It is comprehensive yet accessible. And it leans on a modern understanding of mental health in what is referred to as the biopsychosocial model. This book makes it clear that mental health isn’t simply a “chemical imbalance.”
  •           The Way to Love by Anthony de Mello is my favorite book on philosophical and spiritual perspectives on health and happiness. It contains a series of short, simple essays that you can read dozens of times and still find new meaning contained in them. I like to read this before I go to bed as a sort of brief meditation.
  •           Tribe by Sebastian Junger elegantly and simply covers our need for human connection and how loneliness sits at the center of why so many people are anxious and unhappy.
  •           How to Change Your Mind by Michael Pollan is the ultimate beginners guide to psychedelic medicines and how they can be used to help people heal and change in ways that betters their lives.

Thanks Andy! While each person’s challenges are unique, it’s really important to realize that everyone is dealing with their own shit, and you’re not alone in the journey.

What Does It Mean To Be A “Good-Faith Skeptic” & When Is “Bad-Faith” Warranted

Reflections Prompted By A Conversation Between a16z Crypto Leader Chris Dixon & The Verge’s Nilay Patel

“Good-Faith Skeptic.” It’s a characterization that has been tossing around in my head since reading Chris Dixon’s tweet about his interview with the Verge’s Nilay Patel. It was crypto true believer in a conversation with a crypto skeptic, but containing a foundation of mutual respect, curiosity and, I think, a fundamental love of technology. Here’s a transcript of the podcast if you want to click over to the source material.

For purposes of crypto, consider me an optimistic skeptic? Maybe one with less tolerance (and more judgment) of what I consider to be actors in the ecosystem who are greedy, exploitive, or selfish, but also certainly not willing to write off the entirety of what we’re seeing. My most personal interest is in the collective ownership aspects, having long believed that the only structure which can beat the network effects of entrenched marketplaces are cooperatives, where the participants ARE the platform.

But I should also be transparent with you. Nothing else in this post is going to take a ‘side’ with regards to cartoon apes, decentralized token protocols, or stablecoin pegs. Instead this is going to be about skepticism and what gets deemed good-faith or not.

Here are the primary characteristics, for me in this moment, of what it means to be a “good-faith” skeptic:

  • Enters the discussion without desire to win but instead to understand and be understood.
  • Believes accomplishing the above will ‘grow the pie’ of understanding for general benefit, rather than carving up a fixed pie.
  • Can be hard on the problem without being hard on the person.
  • Accepts that they may be incorrect, have had a different experience than others, evolve their own beliefs. And gives the other person the same courtesy.
  • Within the confines of the discussion space itself, if it’s shared, protects the other person from abuse and actively discourages ‘their team’ from doing so.

There’s no way this is an exhaustive list but it’s what comes to mind for me.

I don’t think good-faith has to ignore questions of what incentives an individual holds which might cause them to believe a certain idea or act a certain way.

I don’t think good-faith has to be ‘polite,’ in a manner which suggests detachment from realities which could be causing real people real harm.

I don’t think good-faith should include apologies for being in disagreement. You can feel upset or sympathetic for conflict caused by disagreement without being sorry for the disagreement itself.

I hope to be a good-faith skeptic in many cases where I disagree with a group’s beliefs or the current narrative. But this also doesn’t mean that every person or every concept deserves evergreen good-faith. As the saying goes, the master’s tools will never dismantle the master’s house, and I can see some people suggesting that “good-faith” skepticism is disagreement theater, where you have different POVs but still all go to country club for dinner after the discussion.

We live in cyclone of bad-faith accusations but also the world is a place where different people are disproportionately impacted by the current state of the world. I personally would find it challenging to have good-faith conversations with individuals who hold extreme perspectives on limiting human rights.

You tell me, what have you experienced as good-faith skepticism vs bad-faith? Are there other characteristics you look for, or methods for deciding when a person/perspective is worthy of good-faith attention instead of ignoring them?

Most Startups Add Independent Board Members Too Late To Make A Real Difference. Here’s Why.

Think Of Your First Non-Investor Board Member As a Senior Hire, And Not Your IPO Board

Being a CEO and running a startup is hard! So you’d think that founders would take advantage of every resource available to help them out. And for the most part they do. But one gap I see too often is leaving the Independent Board member seat unfilled for long periods of time. Often because it’s scoped as requiring a Director who will be with the company until its exit. When instead it should be thought of initially as “who is a senior outside voice who for the next three years or so can help advise this company’s leadership team.”

Before I make my case for a reframing of the Independent Director, I’ll back up and explain. Every company has a Board of Directors, whether it takes financing or not. Initially it’s often just the founders or executives of the company, but as they take outside financing, some classes of investors negotiate Board seats, meant to ensure there’s input into the company’s pivotal decisions which represent interests of all shareholders. So with a typical venture financing, a three person Board will be established (two ‘common’ seats — often the founders and one investor seat). Then as more capital is raised, the next expansion is often to a five person Board — the two founders, two investors and an open seat. This open seat is usually designated as ‘Independent’ meaning it’s not an officer or employee of the company nor a major investor. Rather it’s someone with perspective, gravitas, expertise, a personal brand, whatever, who adds value to the discussion and can be a steward of the company.

This Independent seat usually sits vacant for quite a while, there are other priorities at a startup! But it exists to ensure the Board is an odd number of votes, and while unfilled, it’s usually assumed that the founder/CEO will be its proxy. As a result, sometimes filling it can be seen as ‘giving up control’ since the vote will shift to an actual human being, who theoretically is weighing in on what’s best for the company, not necessarily the CEO (with the hope being those are aligned of course).

I’ve already written about the value of adding an Independent seat post Series A but my conviction has grown in recent years seeing what I’d call ‘Interim’ Independent Directors in action at multiple of our Series A stage startups. Individuals who are *perfect* for that stage of the business and bring real world perspectives to the conversation. They’re typically senior executives at other larger technology companies, not yet serving on public company Boards but also grown beyond the here’s a few common shares ‘advisor’ slot. It’s of great mutual benefit and the startups are more successful as a result because these folks aren’t just active at Board meetings but do 1:1s with the CEO, help with hiring, provide another non-investor perspective to the company exec team and so on.

Outside of the ‘control’ concern noted earlier (overblown in most cases), the two reasons these seats go unfilled are perceived search costs in finding someone (and actual costs in adding they — they get equity) and too upscoped a notion of who should fill the seat. Discussing the latter solves the former IMO.

At Series A/B you are very unlikely to get the CEO of a public company to take an Independent Board Seat. Yeah if you’re a travel startup the idea that the Marriott CEO should be your Board member sounds great but it’s not a fit early on, for them or you. Instead you’d benefit from, say, the VP Operations at a large hospitality brand, or the COO of a non-competitive larger teach company. These people are all available, identifiable and reachable. The only conversation which has to occur is “let’s think of this initial Board tenure as a 2–3 year role, after which we’ll mutually assess whether it’s best fit.” There! In one easy agreement you’ve removed all the weird stigma about transitioning a Board member and set a lower bar for who should be part of the company. It’s like hiring — you wouldn’t not fill a product lead role just because the Chief Product Office you might need five years from now isn’t currently a fit. No, you’d add the right talent to fit the role at the moment. Think of the Independent Board member the same way!

So go forth and find that person! It’s a chance to add knowledge to your Board, and sometimes even diversity as well (since we know what the venture investors are statistically likely to be…)

What’s To Stop Twitter’s New Owner From Publishing The Company’s Historical Internal Emails?

Selective Leaks of Previous Discussions & Policy Debates In The Name of ‘Transparency’ Would Put Twitter Employees At Risk

Typing “I know this makes me sound like a crazy person but..” as a blog post opener is usually a good reason to close my browser window and take a walk. But hey, it’s 2022, let’s soldier onward…

Since it was announced that Twitter’s Board of Directors and Elon Musk had reached an agreement to pursue a sale of the company there’s been a lot of speculation about how the service could change under his ownership.

Personally I’ve been upfront about my distaste for his style of abusive shitposting, impressed by his will to get things done, and saddened by the lack of vigor from Twitter’s Board and C-suite.

But I believe in capitalism and the will of markets, so if Elon ends up as owner I’m not going to cry liberal tears and close my account ASAP, I’m just going to shrug and see how things do. I’ve already changed my relationship with the service earlier in the pandemic, removing 98% of the accounts I’d previously followed and, as a result, spending much less time letting other people insert themselves into my day. However as the press covers Musk’s antics and speculates what the company’s content policies could be going forward to fit one person’s mutated version of ‘free speech,’ there’s another concern that’s not getting enough attention IMO: what’s about to happen to Twitter employees.

No, not their stock options or employment (job cuts are almost certainly coming but we’re in a robust market for talent and I’m assuming there are already many folks proactively looking for new opportunities), but the internal communications that sit within HQ. Namely, the years of emails and documents that detail debates over policy and legal stances. The chance of these getting selectively leaked by a new owner (or their proxy cutouts) just went up.

Get prepared for what looks like ‘embarrassing’ revelations around off the record chats, correspondence with politicians, poorly phrased questions or suggestions, and even an exploration of possible policy outcomes that seems biased. Yes friends, TwikiLeaks is looming.

Remember Musk has his family office manager use a pseudonym to hire a private investigator to dig up invented pedo dirt on someone who challenged him.

And is grossly slamming Twitter legal and trust & safety executives.

You don’t think publishing some “skeletons in the closet” in the name of transparency is beneath him or his hangers on? Like I said at the beginning, I know this makes me sound like a crazy person….

If I worked at Twitter I’d be using the next few months (the deal is still pending) to reduce my PII footprint, change passwords/2FA accounts and so on. Oh, and Twitter management should offer something like Tall Poppy as a benefit.

Look, maybe I’m overreacting and this would be beyond the pale for the new owner or team, who do need to keep the service running as a business (or at least I think he does, who knows). But the chance of something like this happening just went up and last time we had Pizzagate as an outcome.

What Was The First Concert You Attended?

Madonna, Like a Virgin Tour, June 1985

We recently took our daughter to her first concert, delayed somewhat by, you know, that COVID thing. It was Billie Eilish at the Chase Center a few weeks back. Good show. I’m glad my kid had enough taste to pick an artist that she likely will look back on with fondness.

Part of the fun in watching all the girls rock out to Billie was remembering my own ‘first time.’ Appropriately enough it was Madonna’s Like a Virgin tour in 1985. Radio City Music Hall in NYC. Which wasn’t her hometown technically (Madonna grew up in Michigan) but very much her adopted city, having become a part of the scene beginning in 1978 when she dropped out of college and relocated to the East Village with $35 in her pocket. She’s still in and out of the city — at least one residence I know of, a triple wide townhouse on East 81st.

Madonna played three nights at Radio City that June before moving on to Madison Square Garden. I don’t recall which night we went, but my mother took my and my sister. June 1995 meant I was 11 years old. My sister was six.

I hadn’t heard of the opening band, some local group called the Beastie Boys, but they weren’t very good and people booed. Of course just about 18 months later they’d release an album that became very important to me and begin a multi-decade fandom. But that night the crowd was there for Madonna.

AND SHE SPANKED! I mean, it’s hard to remember how on fire she was at this time. There’s something about an artist at the height of their initial debut. Madonna was a cultural phenomena, a performer who inspired adoration, debate, fashion, outrage. Of course she’s reinvent herself multiple times but for my generation, the Material Girl era was the lasting image.

Do kids still buy t-shirts at concerts to wear to school the next day as ‘proof’ or is that no longer cool? My daughter wears a uniform, and the cool Billie Eilish merch drops on the web, so I’m out of touch with what you’re supposed to do today. She bought a tour poster (now framed and hanging in her bedroom) and a keychain, because her school says you can put one piece of minor flair on your backpack.

I bought THE t-shirt back then.

It said “VIRGIN” in big letters on the back. The bustier was like that rubbery print on material. Maybe it glowed in the dark or that was probably just my hope. I’m sure this shirt is now like hundreds of dollars on ebay and trendy LA stores.

Since that time I’ve seen hundreds of shows. I really do love live music. But seeing an iconic performer on a seminal tour as a first shot sets the tone.

So, what was your first concert?

Keep Your Personal Burn Rate Low To Maximize Your Options

Why ‘Living Below Your Means’ Is One Key To Success & Happiness

$0 per year. That’s what my business partner and I decided that we wanted in salary from our newest venture fund. Or at least it was the resulting impact of declining to take additional capital from our investors and commit our own dollars instead. Now, my salary doesn’t go to zero overnight because we’re still drawing down historical management fees but it’s all downhill from here as those income streams taper and end.

Many of my industry colleagues shared that they too would like to pursue the model we chose but they didn’t have the capacity to do so yet. In many cases this was kind of a bullshit answer to be honest. What they really meant was that they enjoyed a lifestyle that was built around fees in addition to profit sharing, had a high personal burn rate, and were risk averse to putting more of their capital in the game. It might seem like I’m shitting on those folks, but actually it’s perfectly sane set of decisions (VCs are generally risk averse, that’s why they’re usually not founders)! But these same folks should be honest with themselves about their priorities because if they wanted to do what Satya and I did, they could!

It all brings me back to Sam Altman’s tweet from a few years back:

Look, I realize this whole post is about rarified air — I’m not talking about the majority of the population who aren’t afforded these ‘decisions’ and who deserve more of a social safety net (including childcare!) so they can make longterm decisions that improve their lives. But I am aiming at early career tech workers and mid career executives who tell me they want to join a startup but are addicted to that FAANG salary+bonus+RSU. Again, nothing wrong with this career path if you want. The surest way to become a millionaire is to join Google and stay there for a decade.

But if you want to prioritize the act of starting a company, or impacting an early one in a big way, you should expect to take a near-term pay cut. It’s no longer always ramen-levels (many early stage startups pay 50th-80th percentile of BigCo tech salaries — FAANG pay multiples of this), but if you can’t imagine earning less for a few years to make more later, then realize you’re limiting your choices.

Low burn rate isn’t just about being able to leave a higher paying job it also lets you walk away from a bad employment situation in general— the freedom to quit a shitty company.

Nice things are nice. Life should be enjoyed in ways that are meaningful to you. But the more you spend on rents, mortgages, lifestyles, etc the more wedded you are to choices you made in the past and not options you want to preserve for the future.

A Good Investor Can Help You Close Candidates. A Great Investor Will Sometimes Tell You Who Not To Hire.

For Early Stage Startups, You Need Employees To Choose The Company. Not The Other Way Around.

I love helping startups hire, especially early on. Look, companies don’t exist without founders — often when we write our initial investment checks there aren’t any employees — but nothing amazing happens without a team. I’d go even further and suggest that if I could access just a single predictive signal after we’ve made an investment of whether the company has a chance to be successful it would be something to the effect of, “show me the first 20 people on the team.” Not the product, not the buzz, not the sales numbers. The people. Because en masse, smart ambitious talented thoughtful human beings are the best prediction model, especially when they vote with their feet.

Ultimately building a hiring brand and motion is the job of the founders, but investors can help a lot. When we spun up Homebrew, our first operating hire was a Head of Talent (Beth Scheer) because we knew that it made sense to bring an expert on board. And then personally, Satya and I also get involved in supporting founders as they start ramping up the growth efforts. Personally, one of my favorite activities is speaking with a candidate during the latter half of the process, when they already have an offer or are getting close to receiving one. I tell the companies I back that it’s an inexhaustible resource — don’t save it just for executive hires. If there’s anyone you think needs or wants to hear from an investor before committing to the company, you intro us and I’ll get it scheduled ASAP. One caveat though, I won’t tell potential employees just what they want to hear. And if I think it’s a bad hire, I’ll tell the founders and ask them to engage with me on those concerns to make sure it’s been thought through, or referenced, or something to keep an eye on once they join. It’s ultimately the founders’ decision on who to hire, but you don’t take my money for me to just be cheerleader. You take my money because you think we can be additive from outside the org chart.

Yeah, so these “sell” calls/coffees/meetings. I actually don’t think my job is to sell, at least not to sell them something they don’t want. Especially early on it does neither party any good to bait and switch a new hire. You gotta understand why and how they’re making their decision and then engage honestly to supply your POV and answer their questions.

I begin every candidate discussion with two commitments:

First, I tell them that while obviously I’m incredibly enthusiastic about this startup, that I believe people choose companies, not the other way around. And so I consider this opportunity my chance to give them more data and perspective they need to make that decision. But that I won’t tell them just what I think they want to hear, because then I’d lose their trust and they wouldn’t stay long at the company anyhow.

Second, I emphasize that although I’m going to loop back with the founders to let them know we spoke, and provide my general impressions of the conversation, that I’m happy to keep anything confidential. That is, don’t worry about how you phrase a specific question or a topic that might be sensitive. Because anything unspoken is usually an impediment to a good decision.

From there I give a bit of my background with the company to level-set. Then we open up to specific questions the candidate might have. I try to close by understanding where the individual actually is in their decision, and what they still feel like they need to do. And I repeat back to them why I think the company could be a good fit for them (based on our conversation), if I truly believe it’s the case.

Does this all take time and energy? Of course. But I do believe when done correctly, it’s one of the pivotal roles an early stage investor can play for the founders they’ve backed.

It’s Pretty Cringey To Self-Anoint Yourself Any of These Four

Let Others Call You a “Platform,” “Mentor,” “Low Maintenance,” & “Good in Bed,” Never Claim Them

Tall. I can call myself tall. It’s objectively true because I’m 6′ 3″. Sometimes I just joke that I’m ‘tall for tech’ but either way, I’m higher up than average. But there are some things I feel like I can’t just claim about myself. “Easy to work with?” That’s really not for me to judge, you’d need to ask my Homebrew partner Satya Patel. Or the founders we back. But there are four things especially cringey to say about yourself because they *only* matter when they’re said by others.

“We’re a Platform”

Whenever I hear a startup, especially one that’s just launched, declare itself a ‘platform’ I’m like nah, at best you have platform-aspirations. True platforms have more than just webhooks and APIs and partner programs. They have an ecosystem. They have created value for others. They have stable and predictable relationships with those who rely on them. Has any tech company ever just said “We hope to become worthy of being called a platform, but really that’s up to the people who will grow with us. And our job is to attract them, inspire them, support them. We hope *they* will call us a platform.” Someone should.

“I’m their Mentor”

Anything I can write here is going to fail to be as influential as just pointing out there’s literally a Seinfeld episode making fun of “mentors.” Don’t say you’re someone’s mentor; let them say it about you. “But Hunter, by saying I’m someone’s mentor it’s actually a vouch for them,” you insist, “It’s showing they are impressive enough that I’m dedicated to them in a non-casual manner.” Ok, maybe, I can buy this interpretation a little bit, but let me tell you, most people won’t get this. And it risks aggrandizing you and lessening this person you suggest you care about. Let them do it, not you.

Before I move on I guess it’s also fair to caveat this one by saying I refuse to be someone’s mentor nor do I want to be mentored by anyone. I love helping people and guiding them. I have my own role models from whom I seek ongoing help. So if you feel like you’re one of my mentors and I’ve just never called you that, know that I appreciate your care, I’m just not going to say it.

“I’m Low Maintenance”

Has ANYONE who said this within the first 24 hours of meeting you every actually been low maintenance? No! It’s like the biggest neon warning sign appears above their head, with a HUGE blinking arrow pointing down to their head, and giant “NO HE’S NOT” script font arcing through the air.

“Wow, you were pretty easy to work with,” seems like it does require another party to validate. And it probably should be said *after* you work together, not before. And maybe even only applied situationally until enough time has passed to prove that yes you are chill generally, not just when things are going well or when you have the power or when it’s sunny outside.

“I’m Good in Bed”