Make All the Asks

“I didn’t want to bother you.”

“I didn’t want to impose.”

“I didn’t want to show up with my hand out.”

“I feel like if you were interested, you would have said something already.”

“I wasn’t sure if it was ok to ask.”

“I haven’t spoken to that person in a while—it might be too random now.”

Do any of these lines sound familiar? Too often, I meet founders that need something, and feel awkward about asking for it for a variety of reasons. Disproportionately, the ones who hesitate to make the ask are women or people of color—at least in my experience.

Speaking from a position where I often get asked a lot, what I don’t think people realize is what the other half of the exchange is in an ask. If a startup pitches me, for example, they’re not asking—they’re selling their equity. That’s a fair tradeoff (at least, if they don’t think it is, they probably shouldn’t have quit their job to start this company.) If no one ever pitches me, then I’ll have no companies to invest.

And if I know the person, I’d so much rather get a pitch from them than someone I have to get to know from scratch (although I’m happy to take cold pitches anytime, too!).

Pitches, while asks for the founder, are potential opportunities for me. Even if I don’t find the company, it’s an opportunity for me to learn about a new space, or just to be helpful enough where you might recommend a founder come and pitch me later on—and maybe that founder is the next big thing.

Most people like feeling helpful—it makes them feel less alone and more useful to others. An ask is really an offer of purpose to someone else.

“Here’s something you can do to help me,” can be a welcome interpretation of an ask if someone is feeling low on self-worth.

You should never be scared to ask for something you need—because the worst thing that can happen is that someone says no. Anyone who dings you just for making an ask, saying perhaps that you’re too needy, probably was never really going to help you with much of anything anyway, and probably doesn’t add much value to your life.

No person is an island—and getting ahead means getting help from others. An ask is a very simple way to direct those who are interested how they can help—because you probably have a lot of people in your life who would help you, but aren’t sure what you need.

I wouldn’t have gotten my first job in venture capital had I not asked to extend my internship part-time past its original deadline. I wouldn’t have gotten that internship if I hadn’t asked if there were other opportunities after interviewing for a few that I didn’t love.

And if you’re ever concerned about making too many asks, you can ask just one more—ask how you can help someone that you’ve asked for help from.

Social Media and Thought Leadership for Founders

Running a startup consumes a ton of time. Just the immediate priorities seem to take up more than one person’s potential working hours—so it’s no surprise that when it comes to something like social media, many founders have trouble making it a priority.

The consequences of failing to position a founder’s profile aren’t always obvious—and it’s usually all about missed opportunities. Some founders get more press, get speaking opportunities or have an easier time fundraising thanks to leads that started with social media. Does just randomly posting on Twitter mean an automatic Series A?

No, of course not.

But if you have to start your VC list from scratch when you’re thinking of who will fund you next and all of your PR outreach is just a bunch fo cold e-mails, you’re starting from behind the eight ball in a way you wouldn’t have had to had you just participated in the public square that is social media in small amounts daily.

Here’s a primer on manageable things a founder can do to create and take advantage of social media driven opportunities for the benefit of their company.

The Base Layer

The very basic level of participation on social media isn’t posting—it’s listening. There is a public conversation going on around people who need to know about what you’re up to and that you ultimately benefit from having a professional connection to. Being unwilling to listen to that is foolish, because it’s good information—and it’s networking 101. Any relationship you build should start with listening first, and social media, despite what you might think, is no different.

Where you can outsource some of this to interns, researchers, a PR firm, your team, etc. is figuring out who your top 250-500 list is. Take the time to understand that if there was a conference full of people that would be highly relevant to what you were doing, who would they be? It’s some combination of industry leaders, other founders, academics, media, big company folks, etc., but in the end you should know exactly who your best few hundred (or more) potential networking leads are, and follow them. Conferences are actually a good place to start to find these lists of folks, as someone has done the job of curating a list for you. You can also look at the list of who other people in similar positions follow. For example, if you were the founder of a self-driving car startup, checking out who the founders of the other dozen self driving car startups follow might be a good place to start.

Generally speaking, I think Twitter and Instagram are good places to start. Twitter feels like a given, whereas Instagram is a bit more personal, but as long as people don’t have private accounts, they’re fair game. It’s often a good way to figure out if there are hobbies or interests you share in common with someone.

Now that you’ve got your follow lists, I would think about perhaps 10-15 minutes per day as a pretty good investment of time checking out what’s going on around you. Share or retweet what you find interesting, ask questions, comment, etc., but do it authentically. Don’t comment just for the sake of commenting—comment only when you have something to say.

If you took the time to pick out 500 industry people who are ultimately the right people for you to connect to given what you’re doing, and you follow them for 10 minutes a day for the next 30 days, but still have nothing worthwhile to say in response or can’t find anything worth sharing—I think maybe you need to reconsider whether you’re really passionate enough about this industry to be in it for the next eight years.

The Angle

Think about an angle—some unique insight—that you bring to bear into these conversations as you start to post. For example, if you were the founder of some new home workout device, posting about fitness isn’t unique enough. Posting about how hard it is to fit fitness into your routine as a parent of three kids—that’s something unique to you that you could imagine being a magazine article.

It doesn’t always have to be about you and your company either. Maybe there are some people you follow who have created great little routines to squeeze into your day doing everyday things—like doing calf raises stepping up and down from your tippy toes as you wait for elevators. Sharing that type of thing helps build your narrative but it also curries social capital with others—because sharing is a currency you can build up.

Long Form

Medium, LinkedIn and various contributor networks like Forbes are great places to get extended stories out. What is it that you would share if you had the opportunity to give a talk at a conference—this is where that kind of message goes. The best way to write long form articles is to keep your reader in mind—what is the interesting thing you’re giving them that is going to be conversation-worthy for them later. Can you imagine them talking about it later at a networking event? Probably not if you’re writing a post on “An Overview of the Banking Industry” but probably yes if the article is “Is the Fintech Startup You Just Signed Up for Worse than Your Bank?” This would be a good way to talk about ethical issues around money and data, and how your company has made a promise never to sell its user data.

Video

A lot of opportunities for founders to be on panels and on TV come from posting video clips. Just because someone writes well doesn’t mean they’re well spoken and perform well on camera—so showing off your speaking skills on video can go a long way to creating more interview opportunities for you.

If you don’t have the money or time to setup a video studio (Who does?) you might check out a company I invested in called Openreel. Openreel allows you to capture HD quality video from your phone, tablet or laptop with all of the controls available to someone using a professional setup with a director. You can even have someone else do the capturing and controls remotely and it comes with a teleprompter feature as well. It’s a fraction of the cost of rolling in a video crew everything you want to shoot something, and an order of magnitude higher quality and more professional just doing selfie videos on your phone.

With this kind of solution, posting a video once a week isn’t a big ask—especially if you just spend an hour banging out three or four at a time. Similar to the longer form posts, try to think of sharing something meaningful that you want people seeing when they search for you—like why you started your company, what’s important to you about this business, or something specific about your leadership style.

Obviously, when you’ve got multiple types of posts—long form on Medium, videos, etc. you’ll cross post across your various channels. This is also a good spot to outsource. Put someone else in charge of making sure your LinkedIn connections know you wrote a Medium post and vice versa.

Engage Others

One way you can build up your following is by engaging others. Write posts where you pose interesting questions to others—giving those people a reason to share things that you compose, along with your profile. If you’re eventually going to be fundraising for a wellness startup, it might be worthwhile to ask 50 investors about their own wellness routines—or, if you’re looking to stir the pot a little, measure the wellness routines of the founders that those 50 investors backed and point out the likely differences.

Interviews other others are a great way to punch above your weight as you build your profile. Most people are willing to have content composed about them for SEO purposes or even to have something to share to their own audience if you’re willing to do the editing.

Authenticity

Not everyone is comfortable posting every last intimate detail of their lives on social media. The good thing is, no one is asking you to do that. However, it’s not an unreasonable ask that there’s some human semblance of you on the internet that a potential hire or funder can find if you’re asking them to commit several years of effort to helping you. When you post about what’s important to you outside of your professional life you build not only a multi-dimensional image of yourself that might give others a better picture of whether they want to work with you, but it also increases the potential ways to connect with key stakeholders. Maybe there’s a VC that also plays the sport you do, likes puzzles, or who can relate to stepping on their kid’s Legos in the middle of the night—and when you’re a founder, you could use any inroad you can into a conversation.

Bonus Points

Here are three next level media strategies that I think have a significantly high ROI and might actually take less resources than you think:

Podcasts

You can use a tool like Zencastr or even a video capture tool like Openreel to create interviews for podcasts very easily—and a basic suite of Apple software like Garageband can get you pretty far in terms of basic editing. A single interesting podcast interview can hook an investor’s attention and running a show can excellent excuse for connecting with high level stakeholders. Running a logistics startup? Interview the GM of North America for UPS. Got a new parenting app? Interview an influential or celebrity mom or dad.

When you’re starting out, much of the value of doing things like podcasts isn’t necessarily in the building of a big following—although that can happen over time. It’s all about having a reason to connect with someone that isn’t so transactional and that gives them some value, too. Instead of grabbing coffee to pick someone’s brain, which is particularly one-sided for them, invite them to an interesting podcast conversation they can share with their own audience. Instead of cold-pitching the media, bring them onto your podcast to share their expertise.

Surveys

Getting a professionally done survey from a real firm costs about the same as one month’s worth of retainer from a PR firm—but is bound to get you way more in terms of press hits. There’s nothing more sharable on social media than data—so let the numbers make your case for why you’re starting a company in this space. Moreover, why not let customer surveys create leads for you? Google “indoor farming data” and you’ll find Artemis Ag’s (formally Agrilyst) State of Indoor Farming Survey, which added a windfall of leads to their sales pipeline. You can work with a media outlet or professional society to get a whole bunch of potential folks in your target market answering questions that they all want to know the collective answers to.

One Day Conferences

You can book a space and feed everyone in a nice space for less cost and effort than you think—and create a lot of content and connection in the process. In fact, if you just need to break even, you can often get sponsors to cover much if not all of the cost of it. It’s also a good excuse to invite interested investors and get into a conversation with them. You could literally script an entire day of panels that fit with your company’s narrative for a higher ROI than trying to get in front of someone else’s audience for just one panel. It’s more work, sure, but it’s potentially a much more valuable outcome. Besides, if you really are the industry leader you say you are, shouldn’t you be running the go to industry conference?

Newsletters

The most valuable career asset I have is my weekly newsletter that goes out to the NYC tech community. It’s mostly just a collection of events, but it has grown to include a fair bit of preamble and perspective. Imagine you were going around telling everyone that there’s a new revolution happening in the dating world away from just a solitary swipe right/swipe left perspective—and that there’s going to be a backlash about how dating works today. Then isn’t there at least a week’s worth of articles, links, essays and content being put out there already to fill up a newsletter, not to mention what you yourself might have to say about it? Having a weekly, consistent curated stream of news and becoming the industry’s source for your narrative is invaluable—and can also be turned into an asset for others. You can post events, conferences, and links to what others are saying and doing too.

Setting Expectations

Participating in social conversations and thought leadership as a founder isn’t something that is going to pay off overnight—but consistent contributions to this area has a high likelihood of paying off for your company. On the other hand, being a founder trying to raise money when no one’s ever heard for you or what you’re up to, nor have they ever read up on what you’re saying is going to happen in the industry is starting from less than zero.

Plus, if you never invest in serendipity, it’s never going to happen to you. You’ll never get that speaking opportunity at a conference or you’ll never get that inbound from an investor asking “Hey, I read your piece, let’s meet the next time I’m in NYC” if you’re not contributing to your thought leadership profile. I can’t promise when, where, or how it’s going to pay off, but the best time to plant a tree is twenty years ago, and the second best time is now. Trust me what you’ll wish you had been doing this for the past year when you need something to happen to your company that’s a bit out of your control like fundraising, hiring or launching.

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.