How to Break into a Senior Business Position at a Growing Startup

You’ve got a great resume. You went to top schools, trained at a prestigious bank/consulting firm/etc, and you’ve succeeded in the corporate world doing some important and impactful stuff. Now you want to take that skillset over to the startup world and you’ve got a lot to offer. You can bring some serious business chops to a company that is going up and to the right but needs to take it to the next level.

Unfortunately, there are a few hurdles in your way:

1) It’s very difficult from the outside to identify which companies are for real—and also which are at the stage you’re looking for, which is out of the “might not be around next year” stage, but not already a unicorn.

2) You’re not a specialist—so a company at that stage would be hard pressed to hire you as a head of sales or marketing, for example, because there are plenty of people out there who already have that specific skill set with startup leadership experience behind it.

3) You’re at a point in your life and career where you’re not about to chance things on a company that might not be around in six months for zero salary.

These are all reasonable points—but the difficulty is that you’re part of a marketplace of talent where you’re in the mix with lots of other people with, at first glance, similar backgrounds. They’re willing to take a lot more risk for earlier stage positions, getting into companies before anyone has a chance to see if they’re going to make it, leaving very few opportunities open by the time they get to a stage you’re more comfortable with.

Still, these kinds of positions do open up occasionally—opportunities to lead new business units as General Managers, Heads of Business Development, COO’s, etc. The key is to be “nearby” to the opening when it comes up—to somehow be a known and trusted quantity, not just a resume. As investors, we do make these introductions to companies, but we do it with people that we can vouch for.

Accomplishing that means understanding how the key stakeholders, like founders and investors, spend their time. These folks are super busy and have learned to have a really high bar for 1:1 meetings. They’re not just grabbing coffee with any random former McKinsey consultant who wants to “get into the startup world”. If they did, they could fill their schedule with just that—that’s how many such requests they get.

You’ve got to bring something valuable—like talent, money, or visibility.

If you start making introductions to founders based on openings they have, that’s going to get you in the door. I mean, what’s the point of having a Harvard MBA if you can’t connect someone to the very best professionals. Same goes for business opportunities. If your classmates are running various groups within the kinds of companies these people want to work with, you can be an invaluable resource.

Why stop at classmates? If you know that someone from your school or extended network is a lot more senior to you and is seriously influential in a company that lots of startups would want to work with—why not host a meal or event for them to showcase what they’re working on.

Who wouldn’t accept an invite to “A networking breakfast where 7 midstage startups will be able to give short demos to the CEO/COO/Head of Business Development/etc for Big Interesting Company X that has huge reach/distribution/userbase, etc.” Maybe make it sector focused and bring in a bunch of such contacts. You could ask a bunch of VCs who would be relevant for those companies—and only ask that you bring Series A/B and beyond companies to the mix.

Now you’re offering value ahead of making asks for your own career—and doing it in a way that doesn’t require me to have to go for coffee (or in my case, tea) ahead of time with someone I feel like I’ve met a bunch of times before resume-wise.

Money works this way, too—and it’s a way to get in with VCs, especially smaller funds. Smaller funds are always looking for limited partners and co-investors in their deals—so starting an angel group or just being willing to make such introductions in your network goes a long way. You could run the same kind of group suggested above on a regular basis as a way to network with investors.

The point is, you’re aiming to build trust and show that you’re willing to offer value before asking for it. That’s what a founder and investors want to see with a senior businessperson before seriously considering them for positions. They want to know if this person can leverage their network in interesting and smart ways to create opportunities for the company.

Media is a great opportunity for companies as well. For those that want to also create visibility for themselves in the process as a smart and connected executive, how about creating a podcast or video interview series about “Hires that took the company to the next level” or “The next Unicorn”—i.e. the types of companies you want to be talking to. The secret to asking people to interviews is that they largely don’t care what kind of following you have—because they can always link to the interview in front of their following. So, worse comes to worse you’re just an outsourced segment producer for their content—and eventually with enough links, you will have that following. That’s basically the story of the 20 Minute VC—a random 20ish year old just started asking VCs to be on a podcast and, yada yada yada, a couple of years later he’s out with his own fund. The best part about this format is that you don’t actually need to be an expert—you just need to be able to ask good questions.

What this does for you is that it accomplishes the filtering mechanism as well. Instead of asking people “Who should I network with” which people really don’t have time to think about, you’re asking “Who would be interested in this opportunity I have—it’s only open to companies with at least X number of employees, funding, stage, etc. and we’re really trying to bring impressive up and comers to the table.”

Of course, you don’t have to take any of this advice. You could just e-mail me and other investors with your resume attached, request my time to help you (a one way street), and ask which companies are likely to be near riskless, high upside opportunities for you to get lots of employee options in.

Good luck with all that.

How to Rock a Short "Office Hours" Meeting

Whether you’re going through an accelerator or you’re at some kind of speed dating event, short “office hours” meetings present both an opportunity and a problem for investors. It’s a great way to get out from behind the e-mail and actually meet people face to face.

However, it’s a terrible way to get your whole pitch in. There’s just not enough time to convince someone to invest and have a productive back and forth.

So what do you do?

First off, change the goal. The goal is to get another meeting, not to get a check. That starts with the basics. Be professional and polite. A quick thank you for having them make the time is appreciated, especially because they’re likely doing this for a few hours straight.

It’s exhausting—so be excited and upbeat about what you’re doing.

Start off by sharing a quick plan for the 20 minutes:

“Here’s what I’d like to do… First I’d like to establish whether or not we’re the kind of company you would consider and then I’d like to outline the X number of things I think you’d need to believe in order to want to take another meeting with us.”

Describe the nature of your company in terms of stage, sector, etc.

“We’re an enterprise SaaS company solving X problem using Y solution. We’re pre-revenue and we have a team currently building a beta product that will be launched in four weeks. Is this a stage and sector that is a fit with your fund?”

If the person says no, you could ask them for suggestions on who you should talk to, or ask them their best piece of fundraising advice, or frankly, just give them their time back. You could say, “I’m going to e-mail you a description of what we do and a deck—should you meet up with any relevant investors, please feel free to pass this on.”

If they say yes, distill your whole pitch down to a few short things that an investor would need to believe to want to know more.

“For you to be interested, you’d have to believe the following:

That people are willing to pay to protect their privacy online.

That we have a team capable of user acquisition at scale based on our track record.

That the market size justifies venture financing.”

If they take an issue with any of your points, just share with them why you believe you’re right—but don’t try to debate it. You don’t have the time for that.

If you have time, share something interesting about how you do what you do—which, you can of course weave into the answers above—but 20 minutes goes really quickly. With some time left on the clock, ask them if you believe this warrants a deeper dive in another meeting. If they say no, just thank them for their time and move on.

What I Want NYC to Do About Uber

You may have heard that NYC is potentially going to cap the number of cars with Uber and similar services.  

On one side, Uber is adding more cars to already congested streets--and taxi medalians have been capped for years.  

On the other, you'll hear that Uber solves the transportation desert problem in NYC and also makes live easier for riders of color who are used to getting skipped over for rides.

I'm not there yet on whether I have an opinion as to what the right number of Ubers should be in NYC, but I do have a very strong opinion as to the treatment of drivers and other "gig economy" workers.

You see, Uber drivers, Taskrabbits, Relay bike delivery people, etc. are all 1099 workers.  Each individual trip and task is treated as a gig--a one-off project not unlike the way you might, for example, pay someone to design your website or code up an app.  

The problem is that 1099 offers near zero in the way of worker protections for anyone who does it like a full time job.  So, while a W-2 worker has protections around overtime and being overworked, 1099 workers don't have any.

I spoke to an Uber driver the other day.  He talked about the way Uber's rules deal with driving time versus total time.  Uber has a 10 hour limit on driving time--i.e., time on the clock with a rider--but up until recently, had no limit on the amount of time you could drive around trying to get to that 10 hours.  He said it would often take 15 hours to get 10 hours of rider time in.

A W-2 worker would have protections around 15 hour shifts and overtime requirements, but 1099s are SOL.

On top of that, when you take expenses into account like gas, leasing, and insurance, drivers are making below minimum wage.

It's been said that the city is considering putting in minimums for drivers, and I would say that before we cap the number of cars, we should be improving the lives of drivers.  Let's measure time in the car and make sure drivers are *netting* at least the minimum wage for all the hours they're in the car, because you literally can't earn the income without paying the expenses.  

This way, we focus on the first step of making sure Uber and others find a viable business model that doesn't involve abusing its workers.  Then, if it finds it can still exist, then we should figure out how many cars there should be. 

Interestingly, one of the ways it can do this is by increasing utilization--i.e. putting less drivers on the road, increasing wait times, so that each driver spends more time getting paid.  Right now, it floods the system with drivers to decrease wait times for consumers.  I, for one, would wait an extra couple of minutes if I knew that meant fair pay for drivers.

The City Counsel should use its leverage in this cap conversation to force Uber to pay drivers better.  If they really want to avoid the cap, they should be held to a higher worker treatment standard.

Ask Founders What They Really Need: The Quick Story Behind Clare's $2 Million Raise

Last September, I was introduced to Nicole Gibbons.  She's the founder of Clare, a modern paint brand that launched today to completely reinvent the paint shopping experience. 

She came in and shared all of the hassles that make buying paint a terrible experience--the difficulty in picking colors that actually look good with microscopic swatches, the need to go to a store and crossfit your way home with heavy paint cans, not to mention the harmful chemicals that are in so many paint brands.

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She knew all this from being an influential interior designer and detailed how she believed there was a big direct to consumer brand to be built in the space.  

Her plan was to close a bit first, first picking up $800k to start executing, and then fill out the rest.  

I asked her how far she could get with it--and which milestones she'd be able to achieve.  It only got her a handful of key features related to what she wanted for Clare.  I encouraged her to go out for the whole thing right off the bat.  

To a solo, first time, non-technical founder, asking for $1.6mm may have seemed like a lot to ask for for a Powerpoint--but it was so much better of a plan than launching something half as awesome for half the money.  Talking about a stepped raise can confuse an investor (and we are easily confused) as to what amount of money matches up with what goals--when the founder knows what they really need. 

It's so important for investors to recognize that different founders have lots of different views on how aggressive or conservative to be on a pitch--but underlying that sales strategy is a *real* plan that the founder knows they could succeed with if they could be successful with fundraising.  As an investor, getting at that without knocking the founder for their interpretation of what you want to here is the key to getting some under the radar deals that others might have overlooked.

Well, not only did she raise that money for a full launch, but she was *oversubscribed* and picked up some amazing additional investors like Imaginary, First Round, Able and Bullish, as well as the founders of Casper and Harry's.   

I'm excited to support Nicole, one of the most inspiring and dynamic founders I've met, and to be along for what promises to be an exciting and impactful brand in a huge space.  

How the Need for Growth Failed Our Social Network Experience

Just about 10 years ago, I tried hard to keep my Twitter follows to a manageable amount--to people I actually cared about following and either already knew or wanted to get to know in person.

5000+ follows later and I've failed miserably.  

It wasn't my fault, though--because the app itself, like all social networks, succeed around growth.  Every single feature is optimized around growing the userbase and increasing everyone's follower count, which means everyone's following count.  Networks are always telling you who from your contacts has joined and recommends you follow new accounts, even though you still only have two eyeballs in your head and 24 hours in the day.  The end result is that each person's connection to you in an ever increasingly connected network becomes more and more tenuous. 

A few years ago, I went to breakfast with Andy Weissman and he lamented Twitter's "Garyvee feature"--the turning off of the visibility of @ replies to people who weren't following the person you were messaging.  Basically, Gary Vaynerchuk would use the @ feature to message a ton of people at a time as he was scaling his following to try and scale 1:1 conversation as much as possible.  It wasn't particularly scalable as following him became a worse experience.  It was a firehose of listening to him not talk to you and just give shoutouts and the like.  However, when Twitter turned this off, while your stream became easier to consume (and easier for businesses or celebrities to interact with people en masse), it came at the expense of authentic discovery.  You never stumbled into half of an interesting conversation with someone you might want to follow based on the topic.  

There was a time when I thought Meetup Everywhere was going to be the next big thing--a social network that was dedicated to connecting people in real life was going to create a lightweight framework for people to localize the social network experience.  If groups got too big, it would be easy to enable splintering.  I don't know why it didn't take, but I've always lamented the failure of the web to create "neighborhoods" at scale that brought communities together (as opposed to just broadcasting to them like Patch).  

For a brief moment, tech was able to make my world feel smaller and more accessible, but now it doesn't feel that way anymore--and I have a theory that I'm part of a very narrow generation that even cares or notices.

There's an age group where you are old enough not to have Facebook in college, but young enough to be an avid user of tech--and to have used the internet to meet new people, probably through AOL or other forms of chat.  When we used dating apps, they weren't based around double opt-ins.  You regularly heard from strangers.  Ok, so it wasn't a *great* experience, but occasionally you'd find diamonds in the rough--and you had to take some risk around reaching out and getting rejected. 

Roughly speaking, this group probably peaks around 35-43.

Not only did we straddle a unique time in tech, but we also came at the tail end of real life neighborhoods as well.  When I was growing up, I would eat lunch and then run outside to play with my friends.  There wouldn't be any coordination between parents to make this happen.  I would just go ring doorbells to see who could come outside if they weren't already out.  It was just assumed that *someone* we knew--a parent or next door neighbor--would be on our street somewhere to keep an eye out.  

This experience made our local world feel very safe and accessible--where we regularly interacted with new people and made decisions for ourselves on who was safe and fun to play with.  We had positive experiences of meeting new kids and becoming friends all on our own, outside the confines of institutions like schools, camps, or parent organized play groups.  

Now, walking these same streets leaves you with a sense that someone stole all the children.  I'm not sure whether it's screen time or parental fear of abduction, but the kids seem to have disappeared from the street.  

It is this same age group that sought this out online--this same group that used Twitter to meet people and Foursquare to find where their friends were hanging out--in order to recreate the neighborhoods experience.  They built Barcamps and unconferences--semi-permeable spaces that got enough scale, but not too much scale, to facilitate people discovery and high quality conversation. 

I don't think we'll see a new form of social media ever attempt to make this happen again--because I don't think the builders of the next generation of apps ever really had this experience to know that it is missing.  Those that experienced it are now at a different point in their life where they're building families or at least coupled off and not really in network expansion mode.

These days, people gather to play a sport, to protest, to play games online, or to watch something--mostly with people they know are already like minded--and maybe that's fine, albeit a little one-dimensional, but sometimes it's nice just to gather in manageable numbers with people you aren't sure agree with you on everything, just for the sake of gathering. 

Can someone build that in a way that isn't contrived or creepy?