Thoughts on my Wedding Day

I’m getting married today.

At least, if she says yes.

But, assuming that all goes according to plan, I have a few thoughts on how I got here—given that dating and relationships seem to vex a lot of people.

I would say that the most important factor that went into both of us finding someone to marry was that neither one of us felt like we had to find someone to marry to be content. We both spent time developing ourselves and our lives as complete and we weren’t waiting for someone to make us whole—so we entered this relationship not as gap fillers for each other, but as two independent people who chose to be together because it was better, instead of trying to avoid being single.

You don’t need anyone to be content—but it’s very nice to meet someone you want who wants you back.

For me, winning her over was an exercise in self-awareness, patience, and respect. In the past, not only had I been pretty unaware of the other person’s perspective in a relationship, but I thought that getting to the finish line was a function of effort. There were times when I thought I could get someone to like me by trying super hard—by proving I could be the best boyfriend ever, when that wasn’t anything close to what the other person was looking for.

When you find someone who is content with themselves, most of what they’re going to look for in you isn’t how you treat them—I mean, it’s important, but it’s not the only thing. It’s going to be about how you treat others. Aja and I appreciate each other just as much if not more for how we treat our families, our friends, and the authenticity we put into our work than for what we’re doing for each other.

Don’t accept someone that is nice to you but a jerk to everyone else.

A few years ago, I dated someone for whom therapy was an important part of her self development. As part of my development, I decided that if anyone was either critical of me or made a suggestion to me that I would start from a position of acceptance before I was dismissive of it. When we broke up and she suggested that I might get something out of therapy, I went ahead with it. I felt fine and didn’t necessarily have something that I thought I’d get out of it, but I was doing this thing of non-dismissiveness, so I tried it out.

I did one session and in talking about relationships, I realized that while I had tried very hard in prior relationships, I never shifted my perspective to try to understand what it was the other person was looking for in a relationship.

Like, never.

I was too busy trying hard to be nice, to be romantic or loving to focus on being understanding and empathetic. No one wants a bigger version of a gift that they didn’t want in the first place or two of that gift.

It totally changed my approach to relationships (and frankly, was the best free introductory anything I ever did, since I didn’t go back).

Things become a lot clearer when you ask yourself the question, “Am I honestly the person that this person is looking for?” versus “How much do I like this person?” It works really well for someone who, at 39, doesn’t really feel like changing who they are that much—because it’s much easier to answer than trying to figure out if you like someone “enough”.

The last thing that I feel is really important is a realistic sense of what’s important to you.

I’m obviously pretty athletic and into sports—but I don’t really need anyone to do them with me. What I do care about is that it’s going to be ok when I roll out of bed on a Sunday morning at 6AM to go on a ride or do a half marathon.

What I’ve found with myself is that Aja is so accepting of the things that were a part of my life before she arrived, like sports, that I’m more willing to give them up, because it doesn’t become a proxy war for balance in our relationship. When I got asked to play on an ice hockey team this summer, I only signed up for half the games not because she would have had a problem with me playing on all of them—but because it would have been ok.

Frankly, I’d rather spend more time with someone who thinks it’s ok for me to play more hockey than actually playing more hockey.

Aja, I am incredibly lucky to be marrying you today. I love you and I cannot wait to see you later…

… after my bike ride.

Tiny Checks

Not every fundraise is easy and sometimes you wind up having to take a higher quantity of smaller checks than you’d like. On the other hand, some people try and pad the cap table with a bunch of big names or industry vets, even if their check size is small, just to build the network. They have an idealized vision of how easy it’s going to be to utilize everyone once the business gets going.

The reality is that the last thing most founders will have time for is writing up investor updates. They’ve got tons of other things that seem more pressing and the last thing they need is a bunch of scrutiny and questions from people who wrote small checks. Not only that, sending out important information in e-mails to lots of people increases the possibility that confidential information gets out.

Still, I think it’s worthwhile to keep all of your investors in the loop for a lot of non-obvious reasons. Maybe it’s an e-mail or maybe it’s just a quarterly phone call that everyone on the cap table can dial-in to. Whatever it is, here are the benefits of keeping everyone—no matter how small, in the loop:

1) When you don’t hear from a founder, it makes an investor feel unappreciated.

Small investors are people, too—and there’s no upside to having a bunch of your cap table feel negatively in any way about the company. These people all have some expertise and experience, and by never reaching out to them for anything, it can feel like you don’t think they have anything to contribute besides money. No one’s saying you have to throw someone a parade every month for writing a $10k check—but sometimes a little nod of involvement goes a long way, especially given that statistically, most startup outcomes aren’t that great. Maybe one day you’ll be able to write everyone a big check at the end, but until then, taking a “That’s what the money is for!” Madmen approach isn’t a good bed, especially if you ever plan on doing another startup.

2) There’s a Butterfly Effect to not being top of mind and not having info on a company.

Investors talk to other investors, to media and to talent, and it’s great when they can share why they’re excited, in a general sense, about your company—or that they’re excited at all. When you have no information about what’s being accomplished at a company, you’re not got to share anything, and people are going to wonder whether not mentioning you is a signal that things aren’t going well. That’s going to make fundraising and hiring even a tiny nudge harder than it needs to be, and certainly costing you more time than the e-mail update would take.

3) Small investors are more aligned.

The way preference works, small investors who just do early rounds are actually much more aligned with founders than later stage VCs who are looking to pour more in to get a bigger outcome. They may not have as much experience as your larger VCs, but their preference is invaluable if you’re looking for a wide spectrum of feedback. Is it worth going for your Series D or thinking about getting to break-even now? Your seed investors might have a different take and diversity of perspective always makes for better decisions.

4) Sometimes, they can surprise you.

People can have pretty random networks, especially around hiring. By keeping your needs top of mind with regular updates, you might get a lot more out of your early investors than you expected in terms of introductions. Recruiting is one of those things where getting a note that a particular hire has been difficult is much more effective than just posting a job into the ether.

5) You actually might need them.

Setting a precedent for updating your investors should start early—early enough where you might actually need to reach out to them in a pinch. Sometimes, rounds fall apart, and if the last thing they heard was that things were going great, then all of the sudden you’re doing a bridge to make payroll, the likelihood they’re going to be excited to write a check will be pretty small. Even in later rounds, you never know what money they might be connected to and they might be able to hook you up with some random family office that you never heard of to help close a difficult raise.

If nothing else, I also just think it’s a sign of respect. Someone gave you their money (or their investors’ money) and I think besides your hard work, the least you can do for them is just let them know how its doing. They might not have a right to that information based on the legal docs, but it’s just the right thing to do by someone—and it also keeps you in the mindset of being responsible for people’s capital when you’re actually interacting with them. As we’ve seen over the past few years, it wouldn’t hurt our industry to make corporate responsibility a little higher priority.

The Uber that Never Was

Using the proliferation of newly GPS-enabled mobile devices to enable taxi hailing and beat out stagnant incumbent providers was always going to be a big win for consumers. It provided a better service than existing cabs were going to be able to do for at least several years—cutting out lots of unnecessary overhead in the system.

Had it been built differently, it could have been a better company and honestly I’d like to believe maybe even a more valuable one in the long term. Maybe it would have given up short term hypergrowth—but as the standard bearer, it could have helped the whole market get on this path, instead of just landgrabbing.

It could have championed fair pay and a national minimum wage—incorporating it into its brand. Would that have cut into its growth? Maybe—but in the long run it would have created happier drivers and a base of more loyal customers feeling better about their brand.

It could have made HR, diversity and employee experience a priority from the start. There’s no reason why a culture needs to fall apart at the seams in a hypergrowth startup. The damage done to the company’s brand do to internal scandals and mismanagement was an economic reality that was the result of really short term thinking.

It could have made accountability around driver behavior more of a priority, but instead it pulled out of cities that required higher levels of screening.

Instead, we got one of the most lucrative startup investments of all time from a company built off of a legion of drivers unable to make a living wage after expenses, without benefits, and not even classified as employees even when they work for the company for full time hours.

But, the VCs did their job—as designed. It’s a tricky subject, because VCs only exist to make money—not really to oversee the running of these companies as beneficial to the world, unless it gets so bad that it affects the economic outcome.

Not only that, we have other portfolio companies to worry about. So, the extent to which any one VC would be openly critical of another’s portfolio company or the investors behind it is limited by the fact that you’ve got other companies that need their late round money. I have a portfolio where 50% of the investments have founders that come from diverse backgrounds—and yes, I want them to get money from all of the still-active funds on Uber’s cap table that benefitted from the IPO.

So, the extent to which any one fund will call out the other funds on the cap table that sat quietly on the sidelines for three years after Sarah Lacy called the company out in 2014 is going to be somewhat limited. The company’s misogynist culture was well documented before Susan Fowler tipped the scales in 2017 and I don’t recall a single investor saying anything about it up to that point.

What if the early investors—some of whom had decades long reputations for being on the forefront of social issues—had made all of their companies sign diversity pledges and been active and public from day one instead of quiet for seven years? Perhaps I’m being too cynical, but when the problems get this big, I think I’d rather hear “I could have done more” than “I tried”.

Everyone is documenting through e-mail screenshots how they invested or didn’t invest in the early days of Uber—showing off their access to the early deal as a badge of honor, but where are the screenshots of the 2014, 2015 e-mails to the team showing their concern about the journalist harassment issues, driver earnings, or privacy concerns?

The too little too late around Ubers culture created a missed opportunity to build an empowering industry leader on social issues—because, at its core, matching drivers to more work is a good thing. Everyone could have done more and until we acknowledge that, this will keep happening.

What if all of the early investors in Uber had, as part of their criteria, a vetting of how serious the company was at creating a healthy culture and a company that would be an impact trendsetter—either because they believed that was the best way to create sustainable economic benefits, or because that was required of them by their investors?

That’s who really should be driving this—because that’s who the bosses of the VCs are. If all of these foundations and endowments that fund VCs start asking about what their social impact screens are, because they want to make sure their money is improving the world, VCs will start behaving differently.

What if the kind of portfolio diversity, became a sought out feature that LPs look for and not just a nice to have—not just from diverse managers, but from everyone? How many LPs are asking the top tier funds what they’re doing to enforce and oversee values and culture from a board perspective?

Does any fund that invested in Uber fear not being able to raise their next fund because their underlying companies might not perform well around these other criteria? Nope.

Until the underlying money starts shifting, we’re going to see more of the same—waiting until the problems get really bad, only calling things out when the cats are out of the bad and it’s politically safe to do so, and championing business models that come at the expense of workers and economic equality.

The Terribleness of On Demand: Why I Backed Journey Meditation

When I was growing up, I watched Seinfeld religiously—literally every single Thursday night from the premiere to the end without missing a single one. Not only did I really love the show, but I was that committed to it because of the reinforcement I experienced by being part of a community that also watched when I did. The next day, I couldn’t wait to see my classmates and repeat whatever the key line from the episode was. It was almost more enjoyable to laugh about the episode the next day with friends than it was to watch it on my own the night before.

The other nice thing about live, scheduled TV—something I’ve come to appreciate now—is that sometimes there was nothing on worth watching. I would flip through the channels and if I didn’t find anything to watch, I would turn it off.

When’s the last time you hit up an on-demand streaming service, came up empty, and decided to do something else instead?

What else did I do? I might have read a book, called up a friend, or went outside for a walk—all things that as I evaluate my habits today are probably more productive than watching Iron Man for the 8th time or clip compilations of West Wing.

The behavior is even more pronounced with kids today. They know that Frozen is available to watch anytime the mood strikes them. They can ask Alexa to play their favorite song.

They never have to sit through anything they don’t initially like.

Some of the most enriching and enjoyable activities I experience in my life now are scheduled and they involve other real live people… in person.

I’ve been playing on the same softball team for almost 14 years. We started playing in our mid-late 20’s as a way to meet new people. Now, as the number of kids and significant others rises on our team, it’s our way to stay connected with our friends—it’s a thing we make time for to keep people in our lives.

I’ve abandoned going to the gym anytime I want to work out by myself in favor of group classes at Conbody—where I see a lot of the same people on a regular basis and trainers that I’ve become friendly with. Interestingly, social media enhances my relationship with these real life people—it gives me a window into their life outside of the gym so I can see who really loves their dog or who likes photography. This makes my real life interaction with them more substantive. Making time for Conbody classes in my schedule is not only a great motivator, but it provides important accountability. I’m going to hear it if I don’t show up for a week.

Meditation is a similar experience to working out—anyone can find a video or an app to watch, but the experience lacks for the kind of community that is built up when you gather live humans at a particular time to experience the same moment. For a lot of people, getting stuck in your own head for too long isn’t a positive experience. It might feel lonely or the whole thing might be super intimidating.

That’s why I got excited when my friend Stephen Sokoler told me he was building Journey Meditation. Journey is a live, guided meditation experience and a community of participants. Friendly teachers bring their own style and experience to the session and it’s something you make time to participate in on a particular schedule.

If you’ve ever wanted to meditate, were curious about it, or tried other methods that didn’t stick—consider joining a community where there are no spoilers, because everyone is experiencing it at the same time. Meditation is a practice of calming focus—where you exercise your ability to narrow the beam of sensory overload. Technology especially throws way too many things at you at once, and the ability to let what doesn’t matter or what you find distracting from your mission pass around you is a useful defense mechanism for today’s world.

Plus, there’s nothing to lose—because you can try it free for seven days.

It’s been a pleasure working with Stephen and his team, as well as Brendan Dickinson at Canaan who also invested in Journey’s seed round with me.

Certainty on Demand: How Labor Platforms are Moving to Higher Order Work

Over the years, we’ve seen a revolution in how labor is supplied because of technology.

First, we saw simple outsourcing—taking one person doing one job and moving the job over to a cheaper person in another geography. That only worked because you could connect everyone via technology—routing phonecalls, e-mails, design documents, etc. halfway across the world so that working with someone in India was as seamless as if they were on another floor in your building.

As emerging markets start to achieve more equality with the rest of the world in labor cost, that arbitrage starts to go away. The best people start to charge more, or they simply move to the US, and the time and efficiency cost of working with labor for less complex tasks starts to not be worth it anymore.

To gain next level efficiencies, we worked on breaking up the tasks that go into a job. If you have two people, a highly skilled worker and an entry level person, if you could microchunk the simpler tasks, move them over to the entry level person, and make the highly skilled person not only more productive but probably happier.

That gave rise to platforms like Amazon Mechanical Turk on the simple task side of the spectrum or marketplaces like Upwork and Taskrabbit where you want someone a bit better, but the tasks are still pretty straightforward. In all of these cases, workers are working as individual contributors—while one person might be managing multiple people, the workers are not connected to each other as a feature of the platform.

Uber and Lyft largely work the same way. Driving is obviously a more complex task than identifying whether an image has a puppy in it, but lots of people can do it, and as long as the driver doesn’t crash or kill you on the way to the movie theater, you’re pretty much ok getting anyone.

If you needed anything done by someone not in your employ for anything more complicated, you are basically looking at some kind of agency work—because more complicated work generally requires teams of people working together. For the longest time, teamwork was inefficient—requiring lots of overhead in planning and setup to get a team with a variety of skills all on the same page and working together on a complex project.

Every new job or set of tasks was treated as unique and constructing teams was viewed as a challenge—so agency work from McKinsey to IDEO, or your corporate law firm, was very expensive.

That’s starting to change as companies realize that for many aspects of teamwork, 80% of most work frankly isn’t that hard and looks somewhat similar to a lot of the other work. You could build semi-rigid operating plans that cover most of the jobs that come through.

Take Block Renovation. Block takes the stressful and sometimes disastrous process of remodeling and makes it simple. Instead of going out into the market and getting a contractor, which is essentially an agency, and an architect (another agency), it focuses on the 80% of bathrooms where all you’re doing is just taking out old stuff and putting in new stuff. They preselect the inventory of fixtures, create standardized pricing, and vet for the basics of contractor reliability—has references, is licensed, etc. The bar is lower here because the jobs are simpler—and the worst aspect of having work done, the price negotiation, is done upfront.

They’re eliminating the work that a customer needs to do in a marketplace—the sorting, vetting and labor management—and turning it into a service with something of a guarantee, which puts the marketplace aspects on the backend under the management of the company.

In short, they’re offering Certainty on Demand—a term coined by Michele Serro, the founder of Doorsteps. If your job fits their criteria, they’re selling the certainty that at the end of X time, you will definitely have a new bathroom. That’s much easier to do when you’ve taken apart the process and put it back together again in a way that optimizes for getting to the finish line with certainty over and over again at scale.

Investors took notice and gave the company over $4mm in its seed round.

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It’s a model that is starting to get repeated in the market. Bench looked at the process of bookkeeping, realized that 80% of the clients had the same simple, straightforward set of needs, and built in automation to service them more efficiently and less expensively than an accounting firm that treats every new client’s set of needs from scratch. Noken replaces a traditional travel agency quite effectively for 80% of the trips in the market where the person is going to a new country wants to see all the stuff that everyone agrees you should probably see. At the same time, they figure out which customer decisions are major consumer satisfaction leverage points—like the quality of the hotel. Just a handful of choice can make an automated process appeal to the vast majority of the market. These platforms enable automation to solve higher order problems effectively, driving above market revenues for lower cost tasks. Consumers are thrilled with the experience, which often seems like “magic” that they are being served so well on such “low” costs compared to full service agencies. Axiom does this for law—providing “the same” legal service for way cheaper because it has filtered which tasks it makes sense for it to do and has more throughput than a traditional legal firm.

Wethos is now doing this for a variety of higher order labor outsourcing—like website design, PR campaigns, or social media marketing. Creating a new website isn’t a job for just one person—someone needs to think about the site copy, someone else needs to do the visual design, and someone else needs to do the front end coding necessarily to implement that design.

There are a multitude of higher order projects that fit this same pattern—too complex for just one person, but 80% similarly structured to a million other similar projects that came before it. Instead of paying for a full on agency with all its custom overhead, Wethos can quickly spin up a group of people from its curated talent network, give them a framework for collaboration, and help you accomplish your goal for a serious discount to a traditional agency. The full potential of a creative agency is something you wouldn’t have taken advantage of with a project like this—much in the same way that Block Renovation doesn’t need to hire an architect for every new bathroom they give a facelift to, Moving curation behind the curtain is key, too. Why outsource the selection of the talent to the customer when the platform knows who is actually good?

The exciting aspect of these startups is that they can turn on revenues from day one—they often experience solid margins from the beginning, and those margins improve over time as they expand the number of playbooks they research and implement. Wethos will add more verticals of work. Noken will add more countries. Block will do kitchens one day and the list goes on.

Labor will find itself able to complete more task, more appropriately funneled to the right level of work, and business will get more efficient, thanks not only to technology but to thoughtful process design.