‘Show them how smart you are’ wasn’t a very successful way to make friends

Most people think of Imposter Syndrome as expressing itself most simply as “I don’t belong here,” as in “I’m not worthy of this success, am all a fraud, and will eventually fail.” For me it was a bit different. My belief was that I did belong, but barely, and in order to maintain my place, needed to constantly remind people/show that I was smart. Needless to say, this inner voice isn’t a healthy one when trying to work on teams and inspire trust.

I’ve written before around my own challenges outrunning the ‘failure tiger’ nipping at my heels for so many years and how that finally resolved. Now I wanted to get a bit deeper on the Imposter Syndrome side and the two hacks which calmed my anxiety. Assume zen pose…

1. What Would 18 Year Old Hunter Think About Where You Are?

Through a lot of my 20s/30s the meta-question of “am I doing enough? accomplishing enough? fast enough before I’m X years old” was a cerebral echo.

Sometimes people would tell me to calm down, seek balance and so on but this only caused me to think they were trying to make me complacent. “Yeah, whatever,” I’d think while listening to their wisdom, “that sounds fine if you don’t want to succeed but I’ve got plans! [or some variation of that]”

Or I’d hear “when you’re older you won’t worry about having worked one hour less. You’ll prize the [family, religion, hobby, whatever] that you made time for.” But all I imagined was old Hunter forever sitting alone in a room by himself, eating canned peaches and listening to baseball games on a cheap transistor radio. #FailureTiger

What ended up working wasn’t picturing myself in the future, but going backwards to my childhood. “If 18-year-old Hunter saw 35-year-old Hunter’s resume, what would he think?” The answer was he’d be pretty friggin’ excited! He’d think life was awesome and what a privilege it had been to work on interesting projects with interesting people. And how this would likely create several decades more of opportunities for his 40s, 50s, and beyond.

18-year-old Hunter wasn’t stupid. Overconfident, a bit smug, poor grooming habits maybe. But not stupid. And so I decided to trust 18-year-old Hunter more. If he was proud and excited by what present-day Hunter was up to, then maybe I should listen to him.

2. Are You So Good That You’re Fooling All These People?

I’d been lucky to meet lots of people along the way that I considered to be smart and accomplished. Way more so than me. Not mentors, I always disliked that word, but maybe role models? Or people I admired? A reasonable number seemed to tolerate me, perhaps even, gulp, like me? Respect me? Trust me? So I asked myself how did this jive with my own self-doubt.

“Hunter,” I told myself, “let’s review: you believe these people are really smart and perceptive. And you also know that they seem to accept you as someone worthy of their time, attention. So, do you think you’re fooling them all?”

I liked this question because, perversely, the Yes or No answer gave me comfort. Albeit it to different degrees and one much healthier than the other.

If the answer was “No, they couldn’t all be fooled by you” then I wasn’t an imposter. I belonged!

And if the answer was, “Yes, you are such a talented psychopath that while you’re not classically intelligent and don’t deserve to be a part of these circles, you’re able to fool them for long periods of time,” well, then I still got included. Note: I actually think these sorts of people do exist/thrive for periods of time — Talented Mr. Ripley anyone?

For the record, I assume the former, not the latter, as a personal truth.

None of this is meant to imply that I’m totally free of my Imposter Syndrome tendencies but they’ve lessened substantially and I have these two mechanisms for ongoing support. And that means a lot.

In 2010, It Almost Disappeared But Then I Put My, Err, Thumb On The Scale

“This isn’t Disneyland,” I insisted while challenging our team’s recommendation that we remove the Thumbs Down (Dislike) button off the YouTube Watch Page during its 2010 redesign. “We’re. Not. Hulu.”

The Thumbs Up/Thumbs Down feedback options had already replaced YouTube’s Original Five Star rating system. After not surprisingly finding that the majority of Star votes were for One or Five Stars, the team decided to move to a UX which better reflected the binary choice. I honestly don’t recall what prompted the “should we remove Thumbs Down” discussion a year later, although it was likely because (a) it was already causing creator distress to see their videos ‘disliked’ and (b) the rest of the team was smarter than I was 🙂

Actually let me amend that: not just smarter, but more diverse in representation. Although perhaps our overall employee stats still didn’t reflect the breadth of backgrounds our industry strives for in current day, we did know that we wanted our team to look more like our user community than a typical tech company. So I’d like to imagine that the presence of more POVs resulted in one or more people’s lived experiences contributing to the idea, even back then, that platforms had a responsibility to think about trust and safety in a broader manner than just preventing illegal activity.

But I didn’t see it. I wanted the visible feedback loop on content that was objectionable, or untruthful. I thought Thumbs Down would help move the larger media companies to see that they had to play by the YouTube community’s rules — you upload a commercial instead of the actual clip people want to see? Thumbs Down! And I thought that part of being online was being open to “criticism.”

Now in 2021 YouTube just announced they were removing visible displays of Thumbs Down, rolling out progressively across the site. You can still vote Thumbs Down on a video, but those stats will only be visible to the creator and not displayed on the playback page. Simply, in their words, “the dislike count will be private across YouTube, but the dislike button will remain.” Smart.

As one would expect if you’re changing the UX for a product used by 1+ billion people, this was informed by data and intention. YouTube is seeking to “help better protect our creators from harassment, and reduce dislike attacks — where people work to drive up the number of dislikes on a creator’s videos.” In fact, they ran an earlier experiment of this change and saw a “reduction in dislike attacking behavior.” This is good and part of a general industry trend to prevent creator burnout.

So major kudos to the 2021 team doing what I prevented the 2010 team from shipping. They were right then and you’re definitely correct now.

Buying Talent Is More Attractive Than Renting In Today’s Competitive Venture Market

Imagine getting paid a solid salary to sit around and think up new startup ideas, distracted only by the free food and opportunities to sit in on discussions of the latest, hottest technologies. Well, if you were an Entrepreneur-In-Residence at one of the large Silicon Valley venture firms during the last few decades, that was your gig. The quid pro quo was that if you settled on an idea that the firm found to be fundable, you’d give them first shot at backing you, although not necessarily exclusively and certainly not contractually. It was more of an unwritten rule. Repeat entrepreneurs and departing big tech company execs would often do pitstops as EIRs, sometimes even simultaneously at two firms (otherwise known as the circa 2008 Jeff Weiner Flex). But now in 2021 you rarely hear about EIRs and they’re certainly not the golden prize of previous years. Why is this?

VCs think WHY RENT WHEN YOU CAN BUY? In today’s market, where there’s limitless capital chasing “consensus startups” the risk of waiting to write a termsheet is too great. If you believe enough in a founder to invite them to be an EIR you might as well just give them some money on a note and let them iterate with you already pot-committed. Otherwise someone else will swoop in and offer them an alternative. So a GPs incentive is to take a flyer and let the founders explore their interest areas with that capital, rather than as an EIR. If nothing comes of it the company will just unwind/return capital, or worst case, it’s a writeoff for the fund. But that risk is worth taking these days for the large VCs.

Founders RATHER USE THEIR OWN MONEY OR ANGEL MONEY if they’re not ready to take venture dollars. Before you tell me that the majority of founders don’t have their own capital already and/or a network of friends and family that can write them six figure checks, let me remind you that I’m talking about EIRs specifically, which were already predominantly repeat entrepreneurs and/or Big Tech Co execs. A 10+ year bull market means that the significant majority of these people have the capital to self-fund for a bit and/or more wealthy friends than the did in 2011. The end result is that why entangle yourself in an EIR role if you don’t need the salary, don’t need the introductions (VCs are no longer gatekeepers to funding, talent, etc), don’t need the office (seriously, sometimes people just liked a place to go work) and so on.

Sure some entrepreneurs still align with venture firms for co-development or “EIR-like” relationships but they’re not formal, don’t typically involve salary and importantly, aren’t bragged about publicly by the firms (less everyone else try to elbow into the deal). Farewell EIR….

Five Questions With Local Newsletter Author Nick Bastone

I love me a good newsletter, especially one that lets us all keep up with local news in a succinct and actionable way. So when The SF Minute started, I was really excited and it’s been a fun collection of serious and not-so-serious SF stories, links and weekend events calendars. I recently had the chance to ask Five Questions of Nick Bastone, its founder and main author. Here they are!

Hunter Walk: Ok, I read SF Minute every weekday. While the title itself is pretty descriptive on its own, how do you explain the newsletter to people and how’d it get started?

Nick Bastone: Of course. And first off, thanks so much for having me here!

The SF Minute is a San Francisco-based newsletter that highlights the top local stories of the day. Basically, every Monday through Friday, I read through all the local publications and summarize the news that I think is the most interesting and important. The result is an email that takes (get this!) only a minute or two to read.

I started The SF Minute earlier this year sort of for selfish reasons. I wanted to learn more about what was happening in San Francisco and (although we have some good publications here) I wasn’t satisfied with any particular product that brought the news together in a simple way. So, I thought I’d give it a try.

HW: You started your career at Square and Faire, before becoming a tech reporter. Why’d you leave tech reporting (for now)?!? Tech reporters with actual startup company experience are exactly what we need!!!

NB: Good question!

Having worked in tech, I do think it helped me as a reporter in some ways, like having good instincts on which stories to chase and being comfortable talking with sources from the start. But business experience wasn’t everything. At The Information, for instance, I covered Google and a huge part of that beat was reporting on all the antitrust cases the company faced. Working my tech jobs — which were mostly in sales and operations — didn’t necessarily prepare me to report antitrust law or know which DC lobbying groups I should be talking to.

As with most jobs, I think a big key to being a good reporter is tied to passion and grit and being willing to go the “extra mile” (as cheesy as that sounds). And personally, as the pandemic wore on, I found myself becoming less interested in what was happening inside Google and more interested in what was happening outside my window (aka San Francisco).

Also, fun fact, between working at Square and Faire I actually helped start a local publication on the Peninsula called The Six Fifty. It was my first “real” reporting gig, and ever since, I’ve been fascinated by the local news industry and have had the itch to get back in.

HW: My wife and I both moved out here in the mid 90s so we have a few decades of SF under our respective belts, and I gotta say, it *is* pretty depressing at the moment due to the city’s ongoing struggle with what it wants to be and political impotence. How do you think about where SF Minute fits into the zeitgeist — it seems like you are interested in moving people to action in small community-oriented ways, like the trash cleanup efforts.

NB: Early on with the newsletter, I took a pretty firm stance on the trash situation in San Francisco and was comfortable saying, “This place is a mess. We need to clean it up!” I figured if anyone was upset with me advocating for cleaner sidewalks, I’m okay with that.

But trash cleanup is sort of the one thing I’m outspoken about. Other topics I really try to play it neutral, present both sides, and stick to the facts, like any good reporter should. It’s so easy in local news to inject your opinion because you actually live here and you’re encountering the same issues that you’re writing about. But again, I really think it’s best that I stay out of it.

That said, a big part of why I started The SF Minute was to inspire positive change across the city. I don’t necessarily know what that change will be or who it will come from, but my thesis is that if I can present the news in an easy, interesting way and get more people to actually learn about what’s happening here, good things will follow.

HW: In building your readership and business, what’s one thing that’s been more difficult than you expected?

NB: It’s strange. Early on I was worried that people wouldn’t actually like the newsletter or they wouldn’t find it useful. But almost from the beginning, it resonated with people, and (since your readers will understand this, I’ll just say it) I think the “product-market fit” has been there from the start. I’ve had so many people go out of their way to tell me they “love” The SF Minute, and that’s the coolest feeling.

But even while creating something people love, user growth has been slower than I expected. In my head, I thought, “No problem, in a year I’ll have 20,000 subscribers.” And that’s just not the case. My email list right now is just shy of 3,000.

Part of that is starting from scratch. I had zero subscribers at the beginning of 2021, and I don’t necessarily have a huge Twitter following or online presence to drive a ton of growth. And I think part of it is also tied to not taking huge swings on the editorial side. I haven’t really broken that major story that then becomes the talk of the town. I’ve mostly been sticking to my news-roundup approach and growing steadily every week. It just takes time, like a lot of other creative ideas or businesses out there. And I have to constantly remind myself to be patient.

HW: Are there examples of “SF Minute” in other cities that you were inspired by or sought to emulate? Any 2022 plans to share?

NB: Newsletters are hot across the media landscape and local news is no different. Earlier this year, Axios threw its hat into the local news market and took the newsletter approach. There’s another company called 6 AM City that started publishing newsletters for second and third-tier cities in the southeast (think Raleigh, Asheville, and Nashville), and after raising $5 million recently, they’ve been expanding fast across the country. There’s also Andrew Wilkinson’s team up in Canada called OMG that has its own family of local newsletters.

Each company has its own style and voice, but the idea is the same. Again, I think it comes down to simplicity. It’s hard to get people to dedicate a lot of their time to reading local news, so it’s helpful to start with something that feels manageable (and enjoyable!), like a newsletter.

As for me, I’ll see in 2022 if I can turn The SF Minute into an actual business that’s somewhat sustainable. My wife has been supporting me on this journey, but I’ll need to pitch in financially at some point. That might take the form of advertisements on the newsletter or introducing a paid membership model, or both.

But I’m hopeful. Another thesis I had when I started the newsletter was that while a lot of people were leaving San Francisco during the pandemic, the people who stayed had a sense of loyalty about it. They wanted to learn more about what was happening in the city and why that was the case. I still believe that’s true, and I think The SF Minute is in a really good spot to help serve those people who want to make San Francisco their home.

Thanks Nick! Hope everyone signs up for The SF Minute, a free weekday newsletter about SF.

Sure It Doesn’t Ask Any “Hard Questions” But Maybe It’s Okay To Just Appreciate His Journey

I don’t stan. I don’t have heroes or mentors. There are people whom I admire as humans but even then it’s about choices they make and consistency with which they live their lives. That said, I GUESS I LOVE THE ROCK.

Writer Chris Heath and Photographer Mark Seliger do a wonderful job of summarizing what we seem to love about Dwayne Johnson, namely his drive and heart. And Vanity Fair gives them all the pages they need in November’s issue. One of my favorite passages:

The simple, empirical truth is this: Dwayne Johnson is the most successful movie star in the world, and has been for some time. For each of the last five years, he was, according to Forbes’s annual list, either the highest or second-highest paid actor. (In that period, he is estimated to have earned a total of $430.4 million.)

“It sits me down,” says Johnson, mulling this circumstance. “It sits me down. That was never the goal. The goal was just: I didn’t want to be broke. And I didn’t want my family to be broke anymore.”

and

Johnson’s friend Oprah Winfrey detects something distinctive at work here. “Most people have the ‘Do you see me?’ gene,” she says, “but he truly has the ‘I see you’ gene. And I think the reason why he’s adored is because he is adoring of other people…. He really is what he appears to be. And people know that.”

There’s a ton more about his relationship with his family, especially his father, and it’s clear that he’s human, with emotional pain that he carries.

Also, he still has zero respect for #candyass Vin Diesel.

How I Give Away My Money. And Perhaps How You Can Too!

I still insist that we don’t talk enough about money in our community. I mean really talk — publicly, openly, emotionally. Philanthropy (which I’ll define as actively supporting my values with dollars) has become an increasingly important part of my own goals. If you’re in a position to give meaningfully and consistently, maybe my journey will resonate for you. And I should note that what follows represents my POV/approach, some of which is shared by my wife but she also has her own style and I greatly respect that energy.

Four Things To Consider When Donating $10k, $50k, $100k+ Each Year

1. Use a Donor Advised Fund (DAF)

A DAF is a financial instrument where you can park cash, stock, and a host of other investments. You take the tax deduction when you put the asset into the DAF, and then give it away over time, letting it appreciate (hopefully) prior to distribution. It’s a really great tool to help manage appreciated private stock and offset large gains while not having to commit the donated wealth to any one particular 501c3 right away. We try to do all nonprofit giving >$1,000 from ours as well as many of our reoccurring donations.

2. Develop a Framework (or Budget)

Be intentional and consistent. Some folks set a budget — max or min they want to give away each year. I’ve never taken to that strategy, instead focusing on a three-bucket framework:

>> Support: The broadest bucket. If I see a great organization or effort, I donate $50–$250. If a friend who has skin in the game is asking me to donate to an effort they’re spearheading, $50–$250. If I read a news article that gets me mad and I can identify an organization working to solve the problem or opposed the assholes, $50-$250.

>> Support and Amplify: Basically the above but I’ll also put a limited amount of social proof against it. Whether that means via social media amplification, contacting a few friends who might also be interested or allowing the organizers to use my support in their own outreach to others (rare, but in some circles it helps to see people you know also donated). I do this for probably 1 in every 20 donations I make.

>> Committed To Your Success: The 3–5 organizations that I try to give to at meaningful levels each year — four to five figures. Besides writing a check, I’m happy to help their development and program efforts as they would like. In some cases I’ve got a relationship with the staff, in others I’m just another donor in the database, but either way, I remain consistent and step up when asked.

3. Max Out Any Employer Matching

Freeeeee money baby! Seriously, if you’re in a position to do so financially, please take advantage of any employer match. Two months left for 2021!

4. Work With Non-Profits/Beneficiaries To Leverage Your Donation

If you’re giving $1k+ and it’s not in response to a specific campaign or outreach, consider reaching out to the organization pre-donation to see if there are any opportunities coming up where your donation would be more strategic. For example, sometimes they’ll tell you about a program that has a corporate sponsor matching your gift. Most of the time they’ll be too busy to respond or just want to lock in your donation ASAP, so don’t make your contribution contingent on a conversation, but it doesn’t hurt to check.

Three Things I Had To “Get Over” To Become A Good Donor

1. “Aren’t some problems so complex or large or intractable that giving to a nonprofit is a waste? What difference can they make?”

I’ve found that making small donations to issues such as climate, poverty and so on don’t make me think I’m “solving” the problem in one swoop but I approach them as votes for the people and organizations moving towards a better future. Don’t let the complexity of a problem stop you from taking first steps.

2. “But [charity rating organization] says this nonprofit spends too much on operations and not programs?”

There was a period where charities were initially judged by what percentage of operating budget went to direct programs versus infrastructure (headcount, rent, etc). As a blunt instrument this information was better than nothing but it’s short-sighted because it persists the dynamics which cause nonprofits to underpay staff, unable to invest in technology and other capacity building projects, and so on. So yes I want the places I donate to be ethical, hard-working, thoughtful allocators of my capital, but I don’t want them to be under-resourced and risk-averse.

3. “Seems like there are a few new organizations all doing similar things. Maybe I should wait to see who the best one is and just back them?”

Back them all. Or back one of them. Sometimes they’ll all succeed. Sometimes a subset of them will combine. I supported multiple new Get Out the Vote organizations during the last five year, sometimes with overlapping missions. Never regretted a single donation.

And finally, Two Downsides of Being Philanthropic

1. They Sell Their Lists — Especially The Politicians

I wish they wouldn’t list trade, especially the politicians. I’ve given enough to Democratic politicians that my text, emails and voicemails usually contain messages from local, state and national candidates across the US. It’s noise and makes me momentarily annoyed.

2. It Feels Bad To Not Renew A Pledge

Per my buckets above, often I’ll give to an organization on behalf of a person or as part of a specific initiative. Often I won’t give annually to this cause unless my friends continue their involvement. Or every once in a while, I’ll shift one of my “BIG BUCKET” organizations either out of a change in my own priorities or disappointment with a group’s effectiveness. Of course I feel bad telling them I won’t be a donor again, but I’ve found it’s important that your dollars and attention are forward-looking.

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If you’re fortunate enough to have gained wealth from the last decade of technology’s bull market and haven’t yet become an active donor/philanthropist please consider doing so. Thanks!