There is nothing I've ever written that makes me feel older than this post.
"Get off my lawn!"
That's what this post is going to sound like, but I think it needs to be said. There are too many people giving advice who have been through one or two startups, none of which grew into a huge company, got to profitability, or an IPO. I think we all need to be a lot more discerning about where advice is coming from. The startup world, which is supposed to be tolerant of failure, rarely admits when failure occurs. We sugar coat everything and we're so super supportive of each other, we never hold each other to a high standard--making the difference between real success and mediocrity nearly indistinguishable.
How's anyone supposed to figure out who to actually learn from?
For example, as an investor, I've never invested in a company that has gotten to an IPO or a billion dollar exit. I can't tell you how to do that. If that's what you're counting on to learn from me, I'm not your guy. I'm very conscious about what I've done and what I haven't done. I'm good at finding early winners and helping them get up and off the ground, but I've never sat on a board for seven years through all the ups and downs to be around to see a 500 person company ring the bell at the stock exchange.
That's why I'll probably hang around the Canary board a little longer than I would otherwise--to learn from future later stage investors as the fast growing company, now around 20 people, grows over the next few years into a powerhouse.
That doesn't feel like the perspective you get from a lot of advice givers these days. A founder will raise one party round worth of seed money and they'll go teach a class on how to raise venture capital. A BD person at an aqui-hire will write a book on the art of the deal. Growth hacking? Don't get me started. Everyone's an expert there with a participation trophy to prove it.
It's fine when you advise people on how to get hired at a small startup, because you did exactly that, and probably talked to others in the same position. Your advice matches the experience of your accomplishments.
But, managing your career? You haven't had a career yet.
You're like 25.
Yet, it all sounds like awesome advice to other startup people--i.e. other 25 year olds. These represent the bulk of the people commenting, retweeting and liking your posts and sending it viral. They're the ones showing up to the classes you teach. Sometimes, it's good advice. A lot of times, it's horribly misguided, but they'll probably never understand why.
That's because a lot of people don't respect or understand the difference between levels of success. Really successful rocketship riders are often pretty heads down about it. There were tons of people early at eBay or Amazon or Google who worked there for 10 years and had a stratospheric ride up into key positions in the company. They grew with the company and flurished as they learned how to be managers. They'll probably disagree with a lot of what you said about startup careers, but you'll never hear from them.
While what you've done feels successful to you because you're at a startup that has gotten a lot of early downloads for a free app, there are other people who are really hitting it out of the park that possess knowledge and insight that you don't have. Yet, you're out there like you've got it all figured out--you and your PR startegy webinar on how to get covered in Techcrunch while your competitor is getting interviewed on ABC News.
Take this guy, Alex. Alex writes a blog about giving things up. It's funny and entertaining--and generally worth reading for fun.
Alex got fired from his startup job. Not as funny:
"I joined the company eight months ago when it was just three guys with laptops, and I’d watched it successfully launch, raise $3.7M in funding, and expand from 3 employees to 13—three of which I’d recruited and hired. I was proud of my first 8 months at work. I ran a viral email campaign that signed up a person a minute for the week preceding launch, and then generated a firestorm of media coverage when the product opened for business. Shit, I had just released a new version of our website two days prior that improved on-site conversions by 400%.What happened?It’s painfully simple. I excelled at the company’s growth stage because I had a ton of hustle, a lightening fast ability to learn, and the entrepreneurial wherewithal to juggle 30 skills at once. Now, the company had blossomed, hired a new VP of Marketing with twenty-five years experience, and had reached a point where it “needed specialists instead of generalists.”
So... the way in which he fell short was that he was so awesome that he helped the company grow to a point where it didn't need him.
This is like when someone asks you for your worst quality and you tell them that you're too much of a perfectionist.
He then goes on to dole out some career wisdom:
"I would go so far as encouraging everyone to get their ass handed to them along with an Employee Termination Letter at least once in their life. It’s an unforgettable feeling, and getting kicked in the gut by the unforgiving boot of unemployment is a beautiful thing. As long as you have the resilience to counter it with a roundhouse kick to the face."
What? Try to get fired? Umm... I don't see how this is good advice at all. Sure, getting fired isn't the end of the world, but neither is cutting off your left pinky. You likely won't die from it and you'll likely be able to lead a normal life without a pinky, but that doesn't mean it's a good idea.
"You remember friends, right? Those things you pushed aside in favor of late work nights? You know, something other than your laptop’s blueish hue? I thought I did too—but after getting canned, that view changed.
After that fateful Friday lunch, I immediately started calling friends. Close friends. Old friends. New friends. Friends in high places. Friends in low places. I talked to over 40 people in 4 days. So many were unbelievably willing to help. They readily dispensed advice, made intros, and lent sympathetic ears. It was tremendously humbling"
It better have been humbling. Who pushes friends aside in favor of work? I'll tell you who. Assholes. Don't be an asshole to your friends, your family, or anyone. Making time for others and living a balanced life would have made this nugget wholely unnecessary.
So you only learn to appreciate your friends because now you need their help? Last I checked, the definition of friends wasn't "people who can help you find a job." What about what you do for them? If someone ditched me over the last few years in favor of their job, my first response wouldn't have been to stick my neck out for them. It would have been to ask, "Dude, where've you been?"
It's sad that it took getting fired for this guy to appreciate his friends.
"Other than being an affable goofball, there was not one thing I was best at in this last company. Our designer is a better designer. Our engineers are better coders. Our CEO is a better marketer. Our Chief of Staff is a better leader. Yes, I was very good at those things, but was I the best at any one of them? No. Painful, but true.
In other words: I was expendable. That phrase “we need specialists instead of generalists,” already haunts me. It will also be the last time I hear those words. Think I’m going to become a master in my next job? Yep. Better fucking believe it."
This is the most humble section in this post, barely. I'm glad he aims to master a craft in his *next* job, but what he misses out is taking some responsibility for not learning how to do that in *this* job. And was there absolutely no warning given along the way that he wasn't going to be what the company needed in the future? Feels hard to believe that this came out of nowhere--with no opportunity given to him to step up into a bigger role.
The vast number of startup employees at the most successful companies are totally unqualified for their jobs. Even if they have prior experience, they don't have experience at *this* company at *this* particular moment in technology with *this* particular product. It's all new to them and the most successful people adopt, learn, change, and grow.
That didn't happen here and the author never asks why or holds himself accountable for that failure. Why did he fail to see the need for new skills coming? Skate to where the puck is going, dude.
With every hiccup I've had in my career, I've tried to make the best of it, of course, but the first question needed to be "Could I have done better?"
I got hired as a two year analyst at Union Square Ventures--as did Andrew Parker after me. When my time was close to being up and we discussed my next moves as a firm, it just seemed like a normal transition.
When Andrew stayed longer than two years and started sourcing investments--I realized that anything short of surpassing expectations at my job was a failure on my part. Maybe if I had been better, a transition conversation wouldn't have happened. Just because it was only supposed to be two years didn't mean it was written in stone.
That's why, when I got hired for a one year stint at First Round to help them build a presence in NYC, I made it a point to say that my goal was to be indespensible. It was kind of a crazy thing to say when they had plenty of east coast coverage and no partnership positions available. Instead of one year, I was kept on for a second year and I wound up leading seven investments while I was there. That wasn't even supposed to have been my job, but it didn't matter.
Surpassing expectations was my job--and even then, I was still trying to be good enough for them to add on a *fifth* east coast partner. Of course, it didn't make sense economically, but working on the things that would have made that even a consideration was still in my head. For example, why didn't *I* find Birchbox before anyone else? I was at that Internet Week when Katia and Hayley were networking pre-raise. Who didn't I talk to there that I should have that would have introduced me? Why wasn't I in Makerbot? I knew people from NYC Resistor.
So before you concede that you aren't a fit for something, or that some outside force prevents you from success, try being a bit tougher on yourself. Resist putting on the spin of a happy post-mortem and be honest with yourself about what you might have been capable of had you done better. You'll thank yourself later for kicking yourself in the ass instead of patting yourself on the back every time things don't go your way.
I've been dolling out career advice ever since I walked into college with a paid internship in finance. I seemed to know what I was doing, so lots of people asked me for help. I spent a lot of time thinking about what seemed to be driving my career and the paths of others, because I wanted to make sure I really believed that the advice that I was sharing could work.
I focused a lot on personal branding. Given that fostering my own personal brand online has propelled much of my success, I certainly believed in it. I told everyone to start a blog--and I believe that. Journaling is a great way to make sense of all of the disparete information that gets thrown at you everyday. A blog is also a mental portfolio for knowledge workers. It's how I understand the thinking that you bring to the table that facilitated the accomplishments on your resume.
There was only one problem.
Blogging is hard.
As I come up on the 10th anniversary of my blog, I know well what it takes to maintain a blog. When I started in early 2004, very few people were blogging--and then I watched blogging take off. It seemed like everyone was starting one. Keeping up with it, however, proved to be a big challenge. Eventually, people went in one of two directions. Either they went pro, which led to publications like Techcrunch, or they just went silently into the night. The web is riddled with dead blogs and rare is the consistant indie blogger who just writes because they like to.
Still, I trudged on with the same advice, until recently. I came to the realization that if no one was going to take it and it was too much trouble, what was the point. It became like the diet that advises you to stop eating everything you like. It might work in theory, but fails completely in practice.
Even when you do keep up with it, blogging sucks in a lot of other ways, too. First off, it's all on you. The nature of the platform is such that it's up to you to create all the content. Sure, you could be a curator like Laughing Squid or Swiss Miss, but it's still up to you to find all these great sources.
On top of that, you have to feel like you have something to say. The act of publishing on the web feels authoritative, and a lot of people can't get past that. A lot of people who actually do have lots to say don't want to come off that way, so they'd rather not put their ideas out there in public. It's a loss to the rest of us, but I don't see what gets them out of that thinking. I've told them to think about it as being a student in public, but that doesn't seem to convince them.
Plus, blog subscriptions have never really been figured out. No one uses RSS anymore, and Twitter is kind of a substitute, but only a small percentage of your followers are going to see the tweet about your new post. Marketing isn't really integrated into the platform at all, so it's up to you to generate your own interest. That's perhaps the hardest thing about blogging. You pour your heart into your writing and for a good long time, no one reads it.
That's when I realized how much more important to me another digital medium had become--my weekly NYC tech newsletter. Don't get me wrong. I love blogging and will continue to do so, but if I had to choose one to keep, it's kind of a no brainer. I can easily say that the weekly note I send out to over 8,000 people a week in the NYC tech community is a far more important channel for me than my blog. That's why, for the first time, I told a friend who said she wanted to start blogging that she should think about starting a newsletter instead.
I gave her the following reasons:
- When you come up with a structure that isn't just writing, curation is easier. My newsletter started out as a pure events newsletter. I didn't even have to write anything, and people would reply every week asking to post events. If you start adding things like jobs and links, they'll do the same, and you don't have to do that much work. You could have a submissions button on your blog, but that feels like a much higher barrier than having someone just hit reply. When you curate, this takes the pressure of feeling authoritative off. It comes off more like, "Hey, I'm just trying to be helpful by sharing this cool stuff that I found with you."
- A newsletter works with a small group--because the readers are self selecting for being *really* interested. An inbox is pretty personal--so if someone is going to let you in, they're going to have to find what you write pretty valuable. The engagement statistics on my weekly newsletter blow my blog out of the water by far.
- E-mail is the best feed reader, especially on mobile. Everyone knows how to type an e-mail into a box. It's an easy sign up process and it's right in people's workflow. Plus, over a third of people's time on their phones is in their inbox. Compare that to how few people have actually downloaded a mobile RSS reader.
- You can still blog in a newsletter. If you're curating links, you can add your own to the list when you've got something good. I do that all the time, but not with every single one of my posts. Link to a blog you keep on Medium. That feels like a good place to write when you don't write that often. You can also just post your thoughts directly in the newsletter if you'd like.
- Newsletters are more easily monetized. Because of the high engagement rates and self selection of the audience, it's easier to make money off a newsletter. I could put an ad on my blog, but who's really going to get excited about a banner on the web. On the other hand, if you've got a message you want to send out to 8,000 people in the tech community in NYC, right into their inbox, that ad feels like a more compelling value proposition.
Newsletters aren't perfect, though. There are still a lot of things broken in the newsletter world.
- Discovery sucks. There are some really great under the radar newsletters out there and it's tough to find them.
- Curating content is a bit clunky. There's no easy way to get from a cool link to e-mail html. You basically have to cut and paste everything yourself, and if you have a custom template, there's going to be some handcoded html in there as well. Plus, there's no easy way to work the submissions process. People ask me to post ads, but managing the text ad, the link, and the payment is full of duct tape and bubble gum.
I'm looking into ways to fix this and business models around it. If you write a newsletter with a strong, engaged following, I'd love to chat.
Storytelling is one of the most important skills you can have as a founder. You tell stories to investors, customers, potential new hires, the press and partners. The key to telling a good story, and what I find most often lacking, is the ability to put yourself in someone else's shoes.
Who is this person and what about this story are they going to care about?
You can, and should, tell the story of your business a hundred different ways if you're telling it to a hundred different types of people. An investor wants to understand how this is going to make them rich. A potential hire wants to understand why this is going to be a cool place to work. A reporter needs this article to turn into pageviews. Every line in your story needs to be delivered with that context in mind.
Key to that is realizing your role. When you get into a pitch meeting, it isn't a press conference. It's a campfire. The story doesn't move forward based on the questions from the audience--bobbing and weaving at the whim of the investor. It moves because you move it. You're walking them through, telling the story that you know will excite them. You need well timed exclamations, pauses--it's a production, not an inquisition. You drive. I want to get taken for the ride of my life. All day, people send me boring stuff--be the most exciting thing I've seen today. Be the thing I can't wait to tell my significant other about.
If you're not literally imagining this investor opening the door to their place and tripping over themselves to tell their significant other about your company, then you're never going to capture your attention. You need to understand why that particular person will get excited about what you're doing. A good storyteller tailors to their audience and knows what will excite and delight them.
Last night, at a New Years Eve party, I asked a few people if they had any resolutions for 2014. It was a mix of the usual--get more sleep, wake up early, eat better, go to the gym, get something accomplished at work, etc.
No matter what people said, though--it all seemed kind of... well... fragile. When you resolve to do something, so many things could get in the way, not the least of which is a change of priorities. Maybe running a marathon isn't going to be nearly as important to you by the time November comes.
That's why instead of resolving to *do* anything, I'm thinking about the ways I could resolve to *be*. I may or may not break 2:30 in my triathalon, but I can be more attentive, be a better friend, be more organized, more thoughtful and more curious.
Goals about what kind of person I want to be keeps me focused on the drivers and intentions, not the results. If you can change your intentions, it's like fixing the operating system versus changing up the apps--and everything will run closer to the way you want it to.
There is a controversial interview with Paul Graham floating around and I'm left to wonder why we're still paying attention to guys like him. He is accused by people of being, at best, oblivious and at worst, sexist. I've never sat down with the guy, so I can't speak to that, but I'm tired of hearing about the same voices over and over again when I'm not even sure they're relevant.
Why give more airtime to someone whose peak of influence, and perhaps success, is clearly behind him--especially to talk about topics where he clearly isn't adding value to the conversation. Every time he opens his mouth about founder diversity, he seems completely out of his league to address the topic. I want to hear Paul Graham's thoughts on gender equality and inclusive participation in the Valley as much as I want to hearCharlton Heston's thoughts on gun control.
"God knows what you would do to get 13 year old girls interested in computers. I would have to stop and think about that," he offers.
Well, maybe he should do that... Stop--AND think. As a guy, I know how hard it is for us to do either of those things, let alone do both at the same time. However, in this moment, I think one's career in venture capital depends on changing your perspective.
The biggest question I think VC's face right now is whether or not, in the future, the best founders will look and act like the best founders of the past. Will they come from the same places as today's industry leaders, or from the far corners of the earth and from underrepresented groups? The world is getting flatter than ever before and the white American male is exerting less and less influence over it each day.
If you are a venture capital investor and you're not preparing yourself to succeed in a more diverse ecosystem of entrepreneurs, you're just going to get left behind.
Considering the myopia at the top, it's not surprising that turning point may have already happened for YCombinator. YC's best investing days may be behind it.
YCombinator had a great run from 2007 through early 2009 investing at a time when there weren't nearly as many seed funds and accelerators as there are now. They picked up Airbnb, Heroku and Dropbox.
Since Airbnb, however, it feels like not only is YC missing another billion dollar plus home run, but the percent of companies worth $40 million (a standard YC has used in the press), either by financing or exit, seems low. I'm thinking maybe I found about three dozen companies worth that much in the nearly 400 companies that have been through YC since Airbnb. That's less than 10%. The classes got too big and quality was diluted because, by PG's own admission, YC "grew too fast."
You could argue that the recent companies are too early, so I'll take that challenge and compare it with my own portfolio. Given that they do $17-20k per founder across 350+ companies, we're in the ballpark of the amount of money we're invested--just south of $10mm.
My own track record as a VC across First Round Capital and Brooklyn Bridge Ventures actually starts in January of 2010, *after* the Airbnb class of Winter 2009. I've closed on about 20 early stage investments and, by comparison, 5 of my investments are now worth $40 million or more either via financing or exit (with three more over $25 million). That's 25%... a far higher rate than YC has appeared to have done since then. My total valuation multiple across that span is nearly 4x and the return rate is up over 110% IRR. The initial base of capital has already been returned in those investments, so it's not a made up return based on just paper gains either.
Most relevant to this conversation, though, is that I didn't do it by only funding only hacker dudes in the Valley:
- Nine of my twenty investments have female founders or co-founders--nearly 50%.
- All of the companies but one were funded in NYC, with the other in Boston.
- Of the 20 teams, only half count an engineer as a founder or co-founder.
A couple of years ago, I went to a networking event sponsored by a top tier VC firm. It was held at a trendy Lower East Side bar where the price of the drinks made it the kind of place that a typical NYC entrepreneur would never actually go. The invitees were a who's who of the NYC tech scene--all the most visible folks.
It was exactly how you'd imagine a venture firm to throw a party. You could see that conversation happening:
"Hey, let's reach out to the community. What's the coolest place to go to? Let's invite all the important venture and startup people people we know of--and don't forget to throw in a few women, too."
You wind up a far cry from Shake Shack when that happens, I'll tell you that.
That's when I realized what separates how the next generation of successful VCs will look at the world.
That party was a bet that the best future opportunities would come from an insider network of people already connected to the establishment--that getting the next Google or Facebook meant connecting to the people "in here".
I'm certain, however, that the more interesting stuff is going on "out there". I believe that the most successful companies that I will get to work with over the course of my career will come from people not currently connected to the insider ecosystem, and from people who don't look like yesterday's notable founders. I'm making a huge bet on the people "out there" because they have new ways of looking at things, new approaches to running businesses and are tackling problems being felt most deeply by the people outside the inner circles.
If I'm going to be successful in that world, I better damn well have a view on how to make the ecosystem more inclusive. I need to watch my style to make sure I appear approachable versus authoritative. I need to learn from my mistakes where I may not have done all I could to make people feel welcome and respected--and surely I've made 'em.
My brand needs to be one of a dutiful civil servant in a welcoming city rather than what I see from certain investors--acting like royalty in a place that investors believe is the only one that matters in the world.
The media needs to do it's part, too. Let's stop paying so much attention to what old voices are saying about the establishment, and instead strive to seek new voices and new perspectives. Otherwise, we risk signaling to future generations that these are the people in charge and that nothing is going to change.
We need to send a strong, clear message to that 13 year old girl, the 13 year old black kid, and the 13 year old growing up outside of anywhere anyone thought to call a venture hotbed to tell them that they can be successful and that they'll get the help they need from openminded professionals.