Landing a job in VC: Pick Yourself


You miss 100% of the shots you don’t take. - Wayne Gretzky

When asked about how I ended up at Union Square Ventures, I tell the truth: “I fell backwards into it.”

In the fall of 2012, I was working on building Incline. Our inaugural class was in session and I was spending 90% of my time working with technology companies in NYC to fill their open positions with technical veteran candidates. By the end of the class we had 80 hiring partners signed up from the fastest growing startups to established media companies, like the New York Times and Time Inc., who were growing technical teams.

A few days after Thanksgiving I got a simple email from Joanne Wilson, an amazing supporter from my gtrot days and beyond, introducing me to her husband Fred Wilson. The email said, “He is interested in talking to you about some possible opportunities.”

Our email exchange: 

Fred: “We are seeking to hire someone to run the USV Network

I realize you have your own startup and aren’t looking for something new

But we would love to talk to you about this opportunity.

Would you be willing to come to USV this Friday to meet with my partner Albert and me?

Me: “Not quite the email I expected. Friday morning works for me or I can adjust a few things in the afternoon.

Fred: “yeah, i was pretty sure it would strike you as ‘out of left field’

I quickly scrambled to learn more about the opportunity which was never listed as an open position. The only mention of the role was the from two years prior when they hired the first GM of the USV Network.

I immediately emailed Christina who just finished her two year rotation at USV. She was kind enough to hop on the phone to answer my questions. She also put me in touch with Gary, the current GM of the USV Network who was leaving to start his own organization. Gary met me for coffee the next day and shared more about the role (while stealthily using the time as an interview).

The 48 hours between getting the introduction email and showing up at the USV offices to interview for a job were strange. I never applied to a job or really thought about joining a VC firm. And to be honest, after starting my own company, I really didn’t really know if I would ever be able to work for anyone else. 

I asked why they contacted me. Fred and Albert told me they never posted the job but asked their existing portfolio for referrals where my name came up a few times. I was flattered. I credit it to knowing a number of people in their portfolio through my work with Incline at the time. 

After a great discussion about the role, the firm and the option to continue running Incline on the side, I decided to join the firm.

I’ve now worked here for 14 months and I love what I do. The GM roles are no longer rotational like the 2-year analyst roles, so I’ve got a few more big things I hope to accomplish here.

What’s funny about this to me is that looking back, I don’t know if I would’ve applied to the GM role if it were posted. I don’t think I would’ve picked myself. I would’ve convinced myself I wasn’t ‘right’ or didn’t have the skills or pedigree from an Ivy league school.

Thankfully it wasn’t up to me to decide if I was right for the role. I could have very easily missed the opportunity to learn so much from the USV team and USV Network at the hand of my own fear.

Don’t miss out on a job, a new venture, a degree, or an opportunity because you don’t pick yourself. Be bold.

If you are interested in joining the team at USV, we are running an open process for the next analysts. We don’t require a resume, just that you tell us more about yourself in two quick video answers. I hope you pick yourself or encourage someone else who wants to contribute to NYC Tech and USV. Apply here

Looking for something to do over Memorial Day? Although sometimes stereotyped for it’s rainy weather, Oregon provided a beautiful place that kept us wanting to spend all day outdoors. Rainstorms were frequent but they never lasted more than 20 minutes, nothing an anorak and comfortable shoes couldn’t handle. 

Last Memorial Day, Neal and I spent 4 days and nights in Portland and the Oregon Coast. We originally planned to spend more time on the Oregon coast but kept it abbreviated in order to explore more of Portland. Looking back we did a lot in only three full-days but it didn’t feel like we were rushing from one thing to the next. 

The itinerary from our trip: 

Thursday: Leave NYC after work > Portland
Friday: Portland > Astoria > Cape Disappointment > Cannon Beach
Saturday: Cannon Beach > Tillamook > Dundee Wine Country > Portland
Sunday: Portland
Monday: Portland > Back in NYC afternoon


New Yorkers can hop a 5:45pm Delta flight from JFK that gets you into PDX at 9pm. It’s a twenty-minute cab ride from the airport to a number of hotels in the heart of downtown . Being Starwood loyalists, we chose The Nines hotel.

Drop your bags, grab your rain jacket and head towards the neon donut sign.Voodoo Doughnuts has become a Portland landmark known for it’s pink doughnut boxes and decadent flavors. During daylight hours they attract a line for blocks so take advantage of their 24 hour hours and beat the crowd. We tried the famous Maple Bacon Bar, rectangle doughnut with maple glaze and two slices of bacon on top, and a Dirt one, yeast doughnut topped with vanilla icing piled with oreo cookies.

Ride out the sugar rush out at a local brew-pub. Portland is known for micro-brews with specialities in IPAs and dark beers. Try to find one where you can see the brewing tanks from the bar. We visited Tugboat Brewing Co. which offers a few of their own beers and a handful of other local brews. It’s a low key spot offering board games and an extensive collection of books lining the walls.


If you ask anyone about breakfast in Portland, Mother’s is always mentioned. We tried to leverage our EST jetlag to get in before the crowds. Peppery bacon, tableside french press coffee and local made jam on fresh biscuits are not to be missed. Food was excellent and more than enough to keep you full past lunch. 

Grab a rental car and get out of town. (Pro-tip: You’ll want a low-set fun car, more on this later). Head about 35 minutes east towards Mt. Hood to reachMultnomah Falls. Enjoy the beautiful views along the highway and look out for the left-hand exit to the Falls parking lot. Views only improve as you make your way up the trail in front of the falls. Make sure to wear walking shoes and bring a rain jacket, the 1.2 mile hike to the top of the falls is paved and provides close encounters with the waterfall spray near the base.

After a nice warm-up, head Northwest towards the coast. It’s about two hours to Astoria, Oregon which sits at the mouth of the Columbia River into the Pacific. The city dates back to Lewis and Clark and feels a lot like a smaller San Francisco. Get some fresh seafood as you look north to Washington. Try a few microbrews in a beer flight at Wet Dog.  Rent a bike to explore town or walk around to take in the local coffee culture.

If the weather is on your side, drive North towards Cape Disappointment, Washington. Confession: We saw it listed on foursquare and with a name like that, we were curious what it was all about. This area experiences about 106 days of fog a year. If it’s a clear day, hike the short trail up to the lighthouse. Look for the secret beach along the way.

Head south about 40 miles to Cannon Beach, OR to catch the sunset into the Pacific. We only wanted to spend one night here although most hotels required a minimum of two nights. We landed at the Wayside Inn which provided excellent access to the ocean and town.

Although not the sunshine and swimsuit weather assumed with East Coast beaches, Cannon Beach is one of the most beautiful places I’ve ever seen. The backdrop of green forests rolling into the sand paired with the massive Haystack Rock and Needles sticking out in the ocean is just breaktaking. As the lighting changed with the sunset and moving clouds, we kept mumbling “wow!” and “it’s so beautiful” over and over again. You may experience Goonies flashbacks as parts of the movie were filmed here. After sunset, dine at Newman’s 988 for local seafood in a historic house near the beach.


Take an early morning walk or run on the beach and look for wildlife in the low-tide pools. Giant orange and purple starfish hold tight to the bottom of the rocks and sand dollars scatter over the beach.

Pack the car and head to the popular Lazy Susan Cafe for breakfast. Put your name on the list then pick up some Salt Water Taffy at Bruce’s Candy Kitchenwhile you wait. It’s some of the best so feel free snacking on a few pieces before breakfast.

Head towards Tillamook but be prepared to stop to take in the stunning views of the Oregon Coast at the numerous lookout points. Grab some ice-cream at the Ikea-sized Tillamook Cheese Factory or pick up some road-side raw oysters. Continue south to pick up Highway-22 that takes you into Portland wine-country. You’ll be thankful for a low-centered car on these windy roads. We had a VW Golf that proved a lot of fun for driving an empty, curvy highway carved into Oregon’s forests.

Sokol Blossmer Winery sits in a region known for their Pinot Noir. A tasting event was setup for Memorial Day weekend which had local artists, BBQ and chocolate vendors alongside a sampling of their wines. The ‘09 Pinor Noir was my favorite that I’m keep an eye out for in NYC. The lamb burger from Ribslayer ( was one of the best I’ve tried. If they aren’t paired with an event at the winery, you can pick one up down the road at their store in McMinnville.

It’s about an hour back to Portland from the Dundee winery area so could be done as a day-trip from the city if you don’t have a night to spend on the coast. Enterprise offers a few locations downtown to easily rent a car without a trip out to the airport. We returned to The Nines and set out to explore one of the other Portland neighborhoods. A twitter recommendation from Raphael and Rick tempted us with a promise of a great burger from a Sushi place.

It was about a 10 minute cab ride but well worth the trek. Yakuza has great food and gives exposure to some of the active neighborhoods outside of downtown. We didn’t make it to the Mississippi neighborhood but got a quick tour in a our taxi after dinner. It’s known for it’s art studios, local eateries and, according to our taxi driver, one of the best barber’s in the world. We grabbed drinks in the Pearl district which has tons of different options from gastropubs to nightclubs.


Have you ever had an oyster omelet? Try one at Bijou cafe. Located next to the original Stumptown coffee house, there is normally a wait on weekends but counter space is first-come-first-served so keep an eye out if you don’t need a table.  

Oogle all of the stylish outdoor gear at Tanner’s as you walk towards the Arlington Heights parks. It’s about a mile walk or bike ride to the foot of the park. Rain or shine, stop by the award winning rose gardens and try to spot the top of Mt. Hood from the city-overlook. Pay a small fee to enter the Japanese Gardens to be transported to another world. 

Head back into town to the Rogue Distillery. Ask for their beer bible to custom build your own sampler. I highly recommend the Rogue Dead Guy Ale.

For a light snack, head to The Parish for their oyster happy hour. With their access to the Northwest coast, you can’t go wrong with their raw or parmesan baked oysters. If you’re in the shopping mood, continue to explore the Pearl District shops and don’t forget to check out the massive Nike store in downtown. Realize that 80% of people on the streets of Portland are wearing something Nike as the company’s corporate headquarters are just next door in Beaverton, OR.

Make a reservation at Wildwood for dinner. It helped start the movement of locally sourced food in the Portland food scene. From game to seafood, there is something on the menu for everyone.  Head to Departures to enjoy panoramic views of portland from their outdoor roofdeck. 


Take the 7:00am flight back to NYC for a 3:15pm arrival.

Apps that made the trip:

Being a Starwood loyalist was great but there are plenty of nice downtown hotels worth exploring. I’m a big fan of Kayak (web or mobile) and of course Foursquare and Twitter for getting recommendations from the real locals. 

On the ground, in order of importance: Google maps, Foursquare, Instagram, Twitter and Yelp. 

Mobile Inbox Hack: Create your own Text Expander


Photo and DIY vintage charger idea from Tidbits and Wine

I’m guilty of checking my email within the first few minutes of waking up but I’ve found that I’m less likely to reply to those emails until I’m in the office. I’d like to think of it as a ‘light-weight’ way to ease into work in the morning but what it really comes down to is tools.

I try to take superior care of my biggest tool: my inbox. It’s a very powerful medium I use daily for getting things done.

I’m a big fan of google apps tools like appointment slots, canned responses, and boomerang for gmail. They help me get more repetitive tasks done quickly so I can get back to the good stuff. 

The problem is, sending email from my mobile phone doesn’t have the extra features yet. Fortunately, I just learned at the recent USV Business Development Summit about a way to hack a ‘canned response’ or ‘text expander’ type tool into your iPhone or Android phone without a separate app.

iOS: Put autocorrect to work for you

Create keyboard shortcuts with common phrases is easier than I thought. On your iOS device go to:

Settings > General > Keyboard — Scroll down to “Add New Shortcut”

You’ll have the option to put in a phrase: this is where you can type or paste in the long text you would like to replace. 


Using my calendar appointment slot hack as an example, I copy and pasted in my canned response (making sure not to hide the hyperlink):

Phrase:Grab an appointment slot here:———. Please include your phone number in the invite.”
Shortcut: “ssched”

Now, whenever I type scched anywhere in my phone, autocorrect inserts the phrase above. Much faster!

Other things you can shortcut: address to your office, mailing address, conference call number, or a long website URL.

Android: Use Google Keyboard’s text expansion

Good news for Android users, no app is required if you use the Google keyboard. The process is similar to iOS. Android Police has done a great job of providing a step-by-step how to on the process here.


What other mobile inbox hacks do you use? Share with us in the comments or on twitter @br_ttany

White House invites in tech entrepreneurs: optimism ensues

Optimism is a strategy for making a better future. Because unless you believe that the future can be better, you are unlikely to step up and take responsibility for making it so. - Noam Chomsky 


VetsinTech team at the White House. Thanks for sharing Craig.

Two weeks ago I was invited to the White House’s workshop on Veterans Entrepreneurship.  Including White house staff, there were 90 people who worked together in this workshop. We were all gathered on the edge of what’s possible for transitioning Veterans.

Participants included non-profits, government organizations, private companies and public companies. As readers of this blog know, I have been involved in bridging the gap between technical military veterans and the tech sector through Incline which is now the New York City chapter of VetsinTech.

I didn’t know what to expect but I was excited to be welcomed beyond the White House gates. Upon arrival, we were assigned to one of 9 tables with different topics. I was part of the ‘Tech entrepreneurship’ table, our goal was to brainstorm all of the issues we felt Veterans were still facing in this area.

Read more

How early stage employees ask for help

You’ve been #hustling for the past year at your startup. Your team has doubled and doubled again. What was once ten people huddled in a makeshift office is now a group of fifty people collaborating to make this one idea into a ‘real company.’ 


Grind/Dream poster by Joey Roth.

You’ve never been more excited or more exhausted. You stop to look back at where you were a year ago and are shocked at how little you knew. You took on budget or human resources or design or mobile because someone had to do it. You stepped up to the plate and you did the best you could. You helped get the company where it is today. Although you probably don’t hear it as much as you’d like from your CEO, thank you. Thank you. You are a part of what got the company here today.

The high from looking how far you’ve come quickly wears off when you look back at your inbox. Messages about that upcoming deadline. More engineers coming on board but not enough budget to add more hires who aren’t building the core of the product. You’ve added two people to your team but you still feel like you’re absorbing every loose end. You are the person who took on every challenge before, so why should that change?

Yes, you’ve found yourself reading a blog post about employee burnout but then you catch yourself. Burnout is for other people. Burnout is for people who don’t sleep more than 4 hours a day. Hm, maybe you should read do a little research on how people get by with 4 hours of sleep, you could do that just for a little while, right?

NO! Less sleep is never (#hustle mindset: rarely) the answer. What you need help with is reprioritizing. You have too many things on your plate that you can no longer see what’s important. There is no way that you’re doing an excellent job at too many things. It’s impossible.

How do you prioritize when everything feels business critical? First, not everything is business critical, and if it is, then why aren’t any of the other 20-50 people on your team working on this? Everything is not business critical.

Take a deep breath. Say it with me now: “Everything is not business critical.” Repeat it until you believe it.

Now, how do you know what is business critical? Make a priority list by using three questions:

  1. What am I working on?
  2. What should I be working on?
  3. What would I work on if I had more time?

Read more

Become an office space expert in 5 hours


When looking for office space, a growth mindset can be a huge time suck. 

Startup Founders who want to find and secure office space on their own are at a disadvantage. There is a steep learning curve to get up to understand pricing, build relationships and foresee potential pitfalls. Even if you do get significantly up the learning curve, the opportunity to use that knowledge only happens every few years (at best). 

Even if you have an expert on staff or a trusted broker, their services rarely apply when you’re opening an office in a new office. We’ve had a number of our portfolio companies open second offices in SF, NYC and London. It’s very rare to find an expert in all three markets. 

The best strategy? Focus on finding trusted resources through referrals and get back to building your business. 

If you are thinking of opening a new office but looking for advice? You’re in luck! Two of the experts in the USV Network, Alex Miller from Stack Exchange and real estate lawyer Jason Gelman, are taking their knowledge public in an upcoming Skillshare class: 

How to Find, Negotiate and Build Out Your Perfect Office


If you haven’t visited Stack Exchange’s new office yet, you should attend this class just to see it. Beautiful space, amazing kitchen and private honeycomb offices for all engineers. Did I mention that they’re hiring

If you’re looking for a smaller space or co-working space, we’ve started a public list of startup real estate resources in NYC. Additions welcome.

Don’t go it alone when opening a new office. Learn the basics, lean on experts and get back to work.