Technology

“Friend” is a noun

Photograph by: Shripriya

“Friend” is a noun. When it got turned into a verb, it emphasized the transactional nature of many relationships online. While the meaning differed across platforms, it usually meant it was someone whose updates you wanted to see on a regular basis. The platforms themselves then decided how much you would see, using every minor action of yours (intentional or otherwise), thereby controlling the relationship. The platform maintains the connection for you, and instead of sitting on a couch talking to one person, looking them in the eye, you are speaking to a crowd, none of whose eyes you can see, and hoping that keeps the relationship warmish.

That’s not a friendship. That’s a potentially useful exchange of information. The act of “friending” the person was a one-off initiation of this exchange. Building a friendship, making someone into “a friend,” takes more.

Friendships can be created online, but they require:

  • the ability to form a connection. One way to form connections is to have a shared purpose, goal, experience, or project/effort of some kind. That’s why we feel so strongly about Product-Led Communities.
  • a constructive alignment of values that allows collaboration.
  • getting to know the person, in a nuanced way—what they care about, their sense of humor, how they solve problems, how they spend their time, whether they are an asshole to people close to them.
  • a commitment to show up. Online groups where people intend to show up on schedule, and actually follow through, are much more impactful rather than ones where there is no firm commitment to show up and people float in and out as they choose. The decision to make this group a priority means a lot to the people in the group.
  • enjoyment of the interaction—an interaction with a real friend makes you feel better after than you did before.
  • relaxation, enjoyment, or learning. Interactions when you can be yourself, laugh, not watch every word, or walk away smarter, with a new perspective, are all interactions you will want to have again.
  • time, to develop all these dimensions of the relationship over many months.

As I look back at last year, I realize there were a lot of events, one-off talks, lectures, and hangouts. Some involved icebreakers, which are helpful. There were efforts at “community,” but did those result in real friendships, as opposed to “friending”? Real community, versus minor interactions that are easily forgotten?

A couple of weeks ago, I was on a Clubhouse chat where an influencer told the audience we were all lucky to be on the platform this early because we could 100x our audiences if we did things right. And that would be very valuable. That’s our mindset right now: do this thing because it’s valuable. Hang out here because you can meet XYZ, who might invest in/hire/help you down the road.

There is a place for this and there is definitely value in this kind of transactional relationship. But the internet has skewed toward this worldview because when measurable value is created, it can also be extracted.

But how do you really make the online world less transactional? How do you enable the formation of deeper connections where people are willing to spend the time because they enjoy the company of the other person or group rather than find transactional value in it?

There is value in deeper, more meaningful connections and it behooves us to think about how to create these interactions online. The “value” may be harder to measure immediately, but over the long term, will likely lead to more valuable, resilient platforms, and  therefore a healthier internet.

I’m thinking out loud here. How did you feel about your online experiences last year? Do you want to repeat them? What would you like to see changed or improved? Please reach out—I’d love to discuss (in a non-transactional way!)

55 Questions for Mission-Driven Co-Founders

Photo by Annie Spratt on Unsplash

Early on, when Tesla was still Tesla Motors and hardly anyone had heard of it, co-founders Marc Tarpenning and Martin Eberhard were approached repeatedly by large companies that wanted to throw significant money at them, so they could work on solving their problems. Marc and Martin always said no.

They turned down those offers because they were both clearly aligned around the mission of the company, the product they were building, and their personal goals and ambitions.

They also knew each other really well. Not only had they already co-founded an e-reader company together, but even before that, they’d been meeting for coffee every Wednesday (and to this day, they still do that). They had a mutual understanding that extended beyond the practical aspects of working together; they had shared values and a shared mission.

Not everyone has the opportunity to meet a co-founder serendipitously—but no matter how you meet, you have to establish that same chemistry that existed between Marc and Martin. You need to be united around your beliefs, values, and mission. You’ll have lots of decisions to make, and you’ll change your mind many times along the way. But there are some things that you need to get right from the start—specifically, what the point is of doing all this, and what will make it worthwhile.

Earlier this year, when I was looking for a new partner, I used Jordan Cooper’s 33 Questions to really determine who I was, what I wanted, how I wanted to build our venture firm, and what I was looking for in a partner. It’s a great list of questions and helps people get to the heart of the things that matter.

I realized that a similar list for co-founders could be useful. I started with Jordan’s list, organized it a bit differently, and then added in questions that are more relevant to co-founders of a startup, rather than a venture firm:

Absolutes:
1. What will you never do and never tolerate from anyone on your team
2. What will you always do and demand from everyone on your team?

The idea and the mission:
3. Describe what the mission is, to you.
4. What’s at the core of this company?
5. In the ideal world, describe what this company looks like in 5 years, 7 years.
6. How much does the mission behind this idea matter to you?
7. Pivoting:
— a. If we don’t get traction and have to pivot, would you be okay with that?
— b. How far of a pivot are you willing to make?
— c. Are you willing to wait and come back to the core idea once the pivot is successful?
8. What is the timeframe within which you want to see the mission come to life?
9. What if it takes longer than we think? What options will you consider?
[Note: Sometimes you pick your co-founder before you decide on an idea. In that situation, this whole conversation about the idea could be had more generally, instead of about the specific company you decide to start]

Understanding each other:
10. What is your life’s mission?
11. What is a life well-lived?
12. How do you define success? How do you define failure?
13. Have you failed before?
— a. How did you feel about the experience?
— b. How did you react to the experience?
— c. What did you learn from the experience?
14. What stresses you out? How should I help you handle stress?
15. Who are your closest thought-partners and collaborators and why?
16. Who doesn’t like you and why? Who would you consider adversaries?
17. Who are your mentors?
18. Who are CEOs you look up to and why?
19. What major life events do you envision over the next 10 years?
20. How do you imagine your frame of mind evolving over the next 10 years?
21. What are the life events that have shaped you that I need to know about?
22. How do you learn?

Ethics and Behavior:
23. Have you ever had any issues in the realm of sexual harassment, inappropriate work behavior, legal issues, or has anyone ever challenged or questioned your integrity in a way that might come into focus in the future?
24. What, if any, policies or infrastructure would you want to create to ensure a healthy and ethical work environment?

Values:
25. What are the values that you want to define your company?
26. What will the company and its people stand for and live by?
27. Are there clients or industries you’re morally opposed to entering or serving?

Motivations:
28. What role does money play in your ambitions?
29. Why are you doing this, versus working for a different company?
30. What gets you out of bed each morning?
31. Is winning important to you?
32. How do you measure the impact of your work?
33. Whose opinions of you matter and why?

Compensation:
34. What kind of salary will make you happy and comfortable?
35. What’s your threshold for an exit? Would you be open to being acquired? If yes, how much would you need to personally make in order to accept the offer?
36. How do you think about equity between co-founders? Should we always have equal equity?

Investors:
37. What kind of investors do you want to raise $ from? (values, brands)
38. Who do you already have good relationships with? Who are aspirational?
39. What is the ideal relationship between us and our investors?
40. Is how much money we raise a badge of success?

Roles/how we work with each other:
41. Who is the CEO? It’s got to be one of us.
42. What are the kinds of decisions we need to agree on, and which decisions can the CEO make without consultation?
43. How will we stay connected? What processes should we put in place to be in sync as we move fast? (15 minute phone call/zoom at the end of each day?)

How the team will operate:
44. What are your superpowers, and what do you perceive as mine? How can we accentuate and build around them?
45. What are our strengths as a team?
46. Which responsibilities do you want, and what do you actively not want to own?
47. What are our operating agreements? What standards do we commit to, how will we resolve conflicts?
48. How do you want to build the company, geographically? Where should the office be, or will the company be remote?
49. If it is remote, how will we build culture?
50. What is the culture we want for our company?
51. Where do you think you are weak, where do you think I am weak, and where do you think we are weak as a team? How can we buffer these weaknesses?

Concerns / worries:
52. What do you think is going to be hard, both initially and down the line
53. Based on time together so far, does anything worry you?

First 365 days:
54. What are the most important things for us to accomplish?
55. If we do x, y, and z, what will a great first year in business look like?

This is a long list, but working with a co-founder is a big decision. This process only works if each person is herself. It’s like making unique jigsaw pieces fit together. Pretending to be a differently shaped piece won’t help anyone.

These are the things you need to get right from the beginning, if you’re going to start a successful mission-driven company. This process will take time and it won’t be easy, but it’s one of the most rewarding things you can do.

Where Do Missions Come From?

Clarity Sensor, Image Credit: Clarity

Almost every company has a mission statement, but not every company has a mission. For a startup, a mission is a perspective on how the world will look when they succeed. For example, Michael Karnjanaprakorn’s mission with Skillshare was to make lifelong learning and upskilling accessible to anyone—giving people the agency to craft a career that inspires them.

The idea germinated when Michael saw this problem up close: he had graduated from UVA, but he really wanted to continue to pursue new interests. He didn’t see a place where he could stretch, grow and practice lifelong learning in a deep way.

Michael was sure a solution was already out there. When it wasn’t, he realized that if he had this problem, surely others did, too. It was time for a solution—not just for him, but for everyone. That led to his founding of Skillshare.

Sarah McDevitt founded Core after suffering a debilitating panic attack. Over the next few months, she tried many things, and the only thing that worked was meditation. But none of the options in the market made it easy. With something that requires such a regular routine, the phone apps just weren’t cutting it. As a D-1 basketball player, she always loved coaching teens and so she decided that she would build a meditation product that the most difficult customers—teenage boys and girls—could use easily and effectively. This ended up becoming Core.

David Lu arrived at Berkeley for his undergrad and was astounded that every day, he could look up and see a clear blue sky. When he was growing up in Shanghai, this was rarely the case. As he continued his undergrad, he met fellow students, some from other parts of the world, who were also surprised at how the Bay Area seemed to have such great air (back then) compared to other places.

They realized that the first step in fixing a problem is to know there is a problem. They decided to build the most accurate sensor that could measure air quality. As they installed sensors, they learned that when traffic increased, the air quality got worse. David wanted to empower people around the world with data about their neighborhood, companies about the air their employees were breathing, and cities with information on how they could keep their citizens safe. From this, Clarity was born.

For all these entrepreneurs, a mission was born of a problem they had some connection with and cared deeply about—one they wanted to solve for themselves and also for others. Not every story is just like these, of course. But if you’re wondering where missions come from, look around you.

Misinterpreting “Mission”

Photo by Shaah Shahidh on Unsplash

At Spero Ventures, we’re a single bottom line venture fund: we measure ourselves by our return to our LP.

At the same time, our investment thesis is that we invest in the things that make life worth living: well-being, work and purpose, and human connection. That means we invest in mission-driven founders.

The idea that mission and profit can be tightly bound together is unfamiliar to some people. They ask one of two questions:

  1. How can you be a single bottom line investor and say you invest in mission-driven companies? You have to measure the “impact” the company is having with different impact metrics.
  2. Oh, so you invest in mission-driven founders—that means you’re okay with sub-commercial returns, right?

AAAARGH!!

The company, by performing its core function, should take you towards your mission. And if you have a mission, we believe you will be substantially more successful than if you were not mission-driven.

The words “core function” are doing a lot of work here.

eBay’s core function is to connect buyers and sellers to execute a transaction. By performing their core function, they are fulfilling their mission of enabling economic opportunity around the world. Every transaction on eBay contributes to the mission of giving buyers and sellers agency to live the lives they want.

Tesla’s core function is to manufacture and sell electric vehicles. By performing their core function, they are fulfilling their mission of accelerating the world’s transition to sustainable energy. Every car they manufacture and sell is making the world better by being one more car that uses clean power.

WhatsApp — does this seem like an odd one? It’s not. By performing their core function, they are fulfilling their mission of letting people communicate anywhere in the world, without barriers. Every text, video, and phone call on WhatsApp, whether across ten thousand miles or ten miles, is democratizing access to human connection by making it free.

In contrast, a company like Toms Shoes might be making an impact, but their core function is to sell shoes. The fact that they happen to give to charity is a nice-to-have — it’s not part of their business model; it’s a marketing tactic. They are not a mission-driven company even if they use marketing language about “improving lives.”

Mission is not off to the side. It’s the very heart and soul of the company. It’s the product, it’s the marketing, it’s the company.

And because mission is core, the bottom line is the only thing you need to measure. Tesla doesn’t measure impact separately from its bottom line, because having more Teslas on the road is the impact. At a mission-driven company, when people buy and use your product, your bottom line is going to grow, and there’s a direct connection from mission to the bottom line.

At a true mission-driven company, the business model itself makes life worth living. And we believe those companies have the highest chance of success.

Here are three companies from our portfolio that exemplify this:

Skillshare’s core function is to allow teachers and learners to connect around their creative passions. By performing their core function, they fulfill their mission of inspiring and multiplying creative exploration that furthers expression, learning, and application.

Gencove’s core function is to extract valuable genetic information through low-pass sequencing. By performing their core function, they fulfill their mission of making whole genome sequencing a bedrock of decision making by making it accessible and accurate.

Core’s core function is to get people to stick with consistent meditation and mental health practices. By performing their core function, they fulfill their mission of cementing mental well-being as a pillar of our lives.

Mission can be very beneficial to your company:

  • Your mission is your north star for decision making. Any time there’s a big strategic question, asking yourself whether it takes you towards or away from your mission can help you answer it.
  • It attracts people who believe in the mission: whether it’s co-founders or employees, these are people who are also driven by wanting to see the world be different and to have a direct hand in making this company come to life. It has some side benefits where you don’t have to pay them big company salaries in order to attract them because they are passionate about what they are building and will be more than a cog in the wheel of a large enterprise.
  • Every startup is a rollercoaster. Regardless of how much we want to believe it’s all up and to the right, there will be moments of intense stress and existential angst. When everything is going to shit, you can hold on to your mission and know why you are doing this and use this to motivate yourself and everyone at the company.
  • Customers have started to care about which companies they patronize. If you think about your customers as co-creating the company with you, they will become part of your “cult”.
  • Board of directors: If you’ve had a choice on who funds you and who joins your board, then you could pick investors and directors who are aligned with your vision of where you want to go and what you want the company to become. A clear mission gives you a stronger way to unify them. This is important since they can have a big influence on the strategic choices you make.

At the same time, it’s important to know the place and role of mission in the company.

A great mission without a great business model means very little. Do you have an exceptional business model? At the end of the day, this is the most important aspect of any company. If your business model doesn’t work, the company is going to fail.

This means you shouldn’t put mission ahead of money. They walk hand in hand: If you don’t have a good business model and cannot generate money to survive, you will go out of business. If you go out of business, you won’t accomplish your mission. Game over.

I’ve seen some mission-driven founders treat making money like it’s a bad thing, or making the mission primary and delaying coming up with a revenue-generating model that is sustainable. Mission and business model have to be developed in concert. Fulfilling your core function should generate revenue and move you towards your mission.

In pursuit of that successful business model, you may need to redefine your mission—or achieve it in a creative way. “Purity” of the mission is a false god. You can keep your priorities intact while changing what you do about those priorities. Much like how a film is rewritten when it’s edited, the details of your mission will morph as you find the best way forward.

So ask yourself: Do I care enough about this mission to work hard for the next 10 years? Missions are motivating. Companies are slogs. There is no company that just grows “up and to the right.” Most are nauseating rollercoasters where the highs hopefully compensate for the lows.

But, if you have a mission, with a fantastic business model, where the core function of the company is going to make life worth living, then that is a jewel.

Founder-Market Fit Matters More Than Ever

Photo by Tekton on Unsplash

These days, practically anyone can start practically anything. If you have a sliver of pedigree1, like experience at a reputed company, it becomes even easier.

But as tech permeates everything, people are starting companies in industries they don’t know. In other words, they’re founding companies as outsiders, without strong founder-market fit.

And that’s fine. A fresh perspective is often a huge help. But many industries are complex. The incentive structures, local laws, and nuances about who wins and loses are not obvious from the outside, or even after several conversations with those in the industry. Today, there are over 1,000 seed funds—capital is flowing freely. You will get funded, but that doesn’t mean you’ll find product-market fit, and then get to scale. At any given time, there may be 5-10 companies tackling a similar problem. This is where a founder’s knowledge or experience in the industry is a real advantage.

As my colleague Jonathan Kroll put it:

“The bar has never been lower to build a product. 10 years ago, you’d need millions in investment to have some sort of rudimentary machine learning or computer vision capability. Now, this is all off-the-shelf.

This is amazing! Right?! Well yes, it is—but as a result, building a cheap product with amazing functionality is at everyone’s fingertips. So while amazing products with amazing features could have been the major source of differentiation in the past, today, that’s just not enough.”

Founder-market fit is an advantage because:

  • These founders get to asking the right questions quickly.
  • If they don’t know the answer, they know who to call in the industry to get the answer.
  • “Founders who know exactly what their market needs,” in terms of leverage to move the needle, “might meet those needs faster and in a more capital-efficient manner, therefore extending runway and giving themselves more time to experiment,” said my colleague Sara Eshelman.
  • They understand the incentive structures, and so know how to position their company in the most appropriate (read: unthreatening and helpful) manner to the relevant constituents.
  • They know local laws and where they can push and where they can’t.

Founder-market fit is not developed only by having worked in the industry. You can also be obsessed with a problem in that industry and immerse yourself in it before you find a solution that works.

One example of this is Filip Victor. Filip is the founder of our portfolio company Mati, which is focused on identity verification. He came to the US as a student and faced the challenges of an immigrant: not being able to get credit and not being able to verify his identity with many of the commercial entities that you need to live a life with agency. This led him to spend time learning about the space to try and solve the identity verification problem for people in the developing world.

Another example is David Zamir at Nana. During a tough moment in his life, he taught himself to repair appliances, going out to customers’ homes to fix their washing machines in order to have an income. This led him to create an appliance repair marketplace that trains technicians and enables them to craft their own livelihoods.

Founder-market fit is real when a founder knows enough of the market to see a real opportunity, while knowing how hard it’s going to be. At the same time, founders need to have a bit of rebellion, a bit of chuztpah, a bit of “fuck it, this may really work,” a bit of willingness to upset former colleagues, boldness, and the ability to envision how things could be. That’s when they can take the leap and build a company that could be amazing.


  1. This is a problem and it is exclusionary, but it is also how the world currently works 

Zoommovies, Panpics, and Startupping

Mythic Quest’s Quarantine Episode

Human beings are amazing. A mere two weeks after the lockdown started, most people had adapted to a remote world. Kids were learning soccer on Zoom, personal trainers adapted, cooking and baking classes moved to zoom—but I really did not expect theater and filmmaking to adapt in this world.

But, adapt they did. Zoomtheater and Zoommovies are a thing now, 4 months into the pandemic—for example, Host is a horror movie, made on Zoom.

Are these pieces any good? Well, it depends — film, which is asynchronous (i.e. shot and edited before the viewer sees it), can be just as good. For theater, which is delivered in real time, the remote version is not as good as when the cast and crew are in the same location. But the ability to adapt, the ability to even try this, makes me optimistic.

An image from Mythic Quest’s Quarantine episode

For a polished spin on quarantine filming, look at Mythic Quest, which is on Apple TV. They were filming the second season when the pandemic shut things down. This article outlines what the crew and cast did to shoot a “pandemic” episode that is part of Season 1. They used iPhones with prosumer film software, mics, and shot in all natural light, since lighting is one of the harder parts of filmmaking. They then edited it together to make it look like it was shot on Zoom.

On the other hand, some of Princess Bride’s celebrity cast decided to make a fan fiction, and it’s very clear that it’s shot by non-professionals, embracing the reality of shooting in different locations, with no crew.

In a scene with Diego Luna and Jack Black, they create continuity from two different locations in amazing ways: Diego throws down a green rope tried to a tree in his house and Jack, who is lying on a set of stairs in his house, grabs a hose that is thrown down to him. Diego lifts, Jack clambers, until finally, Jack is back at the top of the mountain (stairs). It’s really well done!

Images from Home Movie: Princess Bride. Image courtesy: Quibi

This would never have been considered acceptable pre-pandemic, but with a new set of rules for the world, there’s a new set of expectations. All film-watching requires the “willing suspension of disbelief,” and for these pandemic-pictures (panpics?), the suspension of disbelief has to be extended. But they are so entertaining!

Theater, unlike film, is synchronous – everything is live. This makes it much harder to adapt to a remote environment. While in film, you can do an extreme close up to show the twitch of an eyebrow, theater acting is “bigger,” so that the person in the last row can have the same read of a scene as someone sitting in the front. So Zoomtheater and the innovations there are harder to adapt to the pandemic. But theater has adapted, too. And if the pandemic stretches out, theater will have to continue to adapt. Imagine if there was a plugin that:

  • allows a lighting tech to set the stage by adding a virtual background and virtual lighting to make people seem like they’re in the same room, with the mood lighting the director wants.
  • controls which person is “shown” to the audience during a live performance. That way, the tech can make sure the right face is shown at the right time.
  • enables a “prop” tech to develop a unique, dynamic set and background for each actor and upload it behind them as the stage changes
  • allows live mixing of the audio so that music can be woven in, like a play.

It’s entirely possible that this could happen. Because despite the insanity in the world around them, humans continue to create, continue to innovate, continue to live lives of hope and splendor. Constraints make them innovate in ways that they wouldn’t have thought to before.

The same is true for startups. Startups have to startup. And the first requirement of startupping is surviving. But the very best startups, like the best creators, use constraints to innovate and thrive, offering customers an unexpected, delightful solution that moves us all forward.

Being Messy

Photo by todd kent on Unsplash

Chanel Miller said her New Year’s resolution for 2020 was to fail as much as possible.

“Making things that are really crappy and undeveloped until maybe they can be good. I’m way too young to confine myself to one lane and lose the ability to openly experiment.”

This is exactly how a the first draft of a film script develops. Characters and ideas float around in your head, and one day, they’re done with the floating and demand to live on the page. The script gets written, and when you’re done… it’s shitty. It’s embarrassing, you don’t want to show it to anyone, and you wonder how on earth your magical characters and ideas amounted to this pile of doodoo on the page.

But, it’s really important to have this first draft. Because as Miller said, yes, it’s crappy and undeveloped, but you need the crappy and undeveloped to have hope for the good and the great.

Struggling, wrangling, failing, crying, working, pushing forward allows your characters and your story to breathe, thrive, and for the bones to slowly emerge from the pile. Experimenting openly, taking the story in unexpected directions, adding or removing key characters, and messing around with no pressure allows the sparks of creativity that makes the script sing.

Every creator needs that messy time.

The same is true for startup creators. Ideas for a product form in your head over time, sometimes over years. Then one day, you’re ready to put it on the “page” — to code something, to craft something. And it may be a sloppy, messy ball of hair, mud, and hope. Don’t clean it up, polish, and shine it in order to raise money too early.

Love your messy stage, because it is so important to relish that stage. You can only do it once for each startup, and it’s when experimentation, ideation, hanging out, and trying weird things is entirely possible. It’s where ugly is awesome.

At some point, a screenwriter will have to share the script with producers. At some point, you have to share your startup with users and, if you want, with investors. If things go well, they love it, and you build an amazing company. Fantastic.

If you’ve grown your company into a wonderfully world-changing one, it’s worth finding ways to go back to being messy. Get into small groups. Make room for experimentation with ugly, creative things that may fail, because that can lead to new lines of growth. If you have the urge to start again, you could start another company and embrace the new ugly ball of mess. Whatever path you follow, the messy part of creation can be the the best part of creation, and the challenge of it makes your ideas and your company better.

Who are you?

Photo by Jyotirmoy Gupta on Unsplash

Every August, US filmmakers rush to make the Sundance Film Festival deadline. And in early December, Sundance announces its lineup. The day before, everyone is equal—all aspiring filmmakers. But the moment Sundance announces, the wheat is separated from the chaff. There are those who will have a film that “premiered at Sundance,” and… there are the other mere mortals. Both groups will now be treated differently as expectations start to diverge.

While companies are less of a lemming-like march to the cliff than film festival applicants, similar rules apply. After a company goes down in flames, or after you get fired, the same thing happens. The very next day, there’s a sense that you’re a different person.

In both cases, I see a similar pattern: people define themselves (and each other) in terms of their successes and failures. But both success and failure are transient and ephemeral. They can both be taken away, forgotten, or overcome. Successes and failures aren’t who you are.

Perhaps, instead of letting successes and failures define you, define yourself according to something no one can take away, something you cannot lose.

If you can lose your job, you are not your job or your job title. If you can lose company, you are not your company. If you always need permission to create or make a film, you are not a creator or filmmaker.

A couple of years ago, someone asked me if I would view myself as a failure if I failed at my job as a venture investor. My answer was yes. I explained that my job is a huge part of who I am, and if I fail at it, yes, I would be a failure.

Since that conversation, I’ve come to a more nuanced view of the world. I wouldn’t say to a founder, “If your company fails, you are a failure.” Quite the opposite. You are not your company, and regardless of whether you took it public or closed it down, you are separate from the entity that is your company.

So, if not by those ephemeral things, how can you define yourself?

  • Instead of defining yourself according to your job description, you can think about characteristics like persistence, compassion, and thoughtfulness.
  • Instead of defining yourself according to successes and failures, you can look at the chances you choose to take. There are second chances, there are third chances—but they only exist if you don’t give up on yourself, and if you actually take them.
  • Instead of defining yourself according to your ego, you can think of yourself as someone who’s always learning.
  • External validation is the bane of humanity. Fuck external validation.

Despite the transience, we let success and failure have such a huge impact on us. Depending on how we deal with it, they can change our life trajectories. But these things still aren’t who we are. Who you are is the amalgam of personal characteristics that make you up. It’s what you learn from success and failure. It’s how you deal with it, and what you go on to do with it. That’s what no one can take away from you, and that’s what makes you who you are.

On Picking Tough Challenges

Photo by Alex Azabache on Unsplash

No one would call Maynard Webb a pussycat. He joined eBay when the technical infrastructure was failing. He was critical to fixing it and making downtime a thing of the past. Anyone who has worked for him would say he was their toughest boss. He was full of pithy Maynardisms that all basically meant, “Stop whining and get back to work.” He was a force to be reckoned with.

Many years ago, in one of our ongoing mentoring sessions, Maynard said something like, “Whenever you’re faced with a career choice, pick the toughest challenge.”

He explained that if you choose an easy problem, you know you can fix it. But, many other people in the world can fix the same problem—there’s nothing unique about the accomplishment. If you choose a really tough problem, you may fail, but if you succeed, then you’ve done something pretty darn hard. That would be rare air.

This is one of those pieces of advice that sounds great. It’s aspirational; it’s the hero’s journey; it’s inspirational. From afar, it all looks and sounds glorious, but the daily reality can be painful. And the chance of failure is extremely high. You’ll work long, hard hours for years, put your lifeblood into something, and likely fail. Not easy.

Founders have self-selected into the toughest path in front of them. The alternatives abound. It would be so much easier to go work somewhere else—somewhere where you’re a member of a team, where many hands make light work, where a decision will not fundamentally affect the success or failure of the company, where the buck doesn’t stop with you.

But the small chance of success is alluring. What if you’re the one to pull it off? You crush that job, or you create that unique company. The highs of that are incredible.

And that is why we are all in tech.

Investing in Founders is like Casting Actors

On the set of “Waking Jed”, directing Jessica Chastain. Photo Credit: Anna Kooris

One of my early lessons in screenwriting was to focus on the character—motivations, personality, drives—and not external characteristics. It’s tempting to specify that the leading lady is blonde, petite, or whatever. And it’s okay to envision the character while writing, but we’re taught to avoid specifying detailed external appearance in casting.

The reason is that sometimes, the best casting decision is the one that’s least expected. You might have an image in your head of the character, but the best actor—the person who is most convincing and does an incredible job—might look very different from your mental image. Let’s say your character is written as a seductress, but the best actor for that role could be more of a plain Jane. That adds a lot to the nuance and depth to the story. A more regular-looking person being a seductress is so much more interesting than the hottest person on earth being a seductress. The film Snowpiercer was written for a mild-mannered man in a suit, but Tilda Swinton rocked the role.

During casting sessions, screenwriters and directors need to learn to set aside their mental picture, look at the actors in front of them, and reimagine the story with each person auditioning. That’s the way to cast the best actors.

Similarly, investors sometimes have a mental picture of who will be a good entrepreneur. It’s not based on looks (one hopes), but on the profile — the experiences a person “should” have had to be a great entrepreneur. VCs can sometimes be biased toward someone who’s worked at a hot company that went public, or is an engineer who can build it all, or a name-dropper who seems very connected in the ecosystem.

If investors carry around these biases in our heads, we will miss the best people. Like great actors, great entrepreneurs can come in all shapes and sizes, and from all backgrounds, all levels of work experience, ages, nationalities, and genders.

When casting an actor, the most important things to look for include:

  • Ability to live the character. Do you believe the actor is the character
  • Willingness to take direction. A director should never tell an actor “how” to play the scene, but the director can and should give her guidance on the mood of the scene, how the audience should feel, or the character’s motivation for a certain action. And the actor should be able to take that input and give the director a range of options.

    I remember when I had the chance to direct Jessica Chastain and James Franco. They gave me such a spectacular performance on the first take and then turned around, asked how it was, and whether I wanted to see it another way. My jaw was on the floor — I was blown away by their talent and their humility in asking for input from a student director.
  • Ability to go with the flow. Film production (especially in the indie world) needs to be flexible. Sometimes, a much-desired location might suddenly become available (for free!), and the crew might have to shoot there tomorrow instead of three weeks from now. This means the actor has to be ready for scene 56 instead of scene 18.

Many of those same characteristics apply to ideal founders:

  • Ability to fully inhabit the role of the CEO. This is about vision, tactical capability, ability to hire, and the ability to sell their vision and themselves.
  • Willingness to take input. An investor should never tell a CEO how to do their job, but a big part of the investor’s role is to see around corners, anticipate challenges based on their experience, and give the CEO input and feedback.
  • Ability to go with the flow. Startups need to be flexible. Sometimes, a new competitor might emerge, you might lose a key person on your team, a pandemic might unexpectedly sweep the globe. The best CEOs are those who can adapt and find a way to thrive in the new world.

Just like the success of a film depends on casting the person who is the best actor, the success of an investment depends on casting the best founder. It requires putting aside the mental preconceptions and focusing on the person in the room (or on Zoom). Despite her youth, can she be an amazing CEO? What gives you that confidence? Her knowledge of the space? Ability to be compelling? Authenticity?

The best casting decisions happen when we are open to allowing incredible actors to show us how much better the character can be. In the same way, I try to approach every meeting with a founder with a willingness to be blown away by their vision of the world.