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Lessons I Learned from My Dad

Lessons I Learned from My Dad Bothsidesofthetable Jun 16, 2013

My mom seems to sneak into my blog from time-to-time. My dad less so. Mom was an entrepreneur and a civic leader. She was (is) a bit of a ball buster. And a negotiator. And a go getter. So she…Read more ›

Why You Should Give Before You Get

Why You Should Give Before You Get Bothsidesofthetable Jun 12, 2013

I have a motto in business and life, “give before you get.” It’s a philosophy, really. And it applies to business relationships & networking as much as it does to remuneration in the workplace. It seems we live in an…Read more ›

When a sales oriented founder's job isn't to sell, but to build a sales team Thisisgoingtobebig Jun 12, 2013

I've had two entrepreneurs I know in the last week come to this same conclusion. Despite the fact that they're great sales founders, selling isn't actually their job. Being the sole salesperson on your team, no matter how good you are, isn't scalable. You need to figure out what it is that you do to sell, the scripts you know by heart that you never wrote out, the way you get a feel for which customers are warmer than others, and find a way to teach it to others. That's the way you build a real business. When you reach product/market fit, companies scale as sales teams scale.

Scaling a sales team is a completely different challenge than being a good salesperson. It's about establishing process, tracking metrics and creating a supportive learning environment. Some people will tell you that half your salespeople won't work out--but that feels a bit like conceding defeat to me. Ideally, I think it's worthwhile to try to build the kind of sales environment where anyone could be successful--where it's about process and learning.

When you're a startup founder, taking your foot off the gas when you know you have something that customers want is incredibly hard. Cash is a drug--and it's hard not to make another customer call to get another hit. You do that and you're taking time away from recruiting and training a team, or figuring out the right individual salesperson economics and incentives. Carefully constructing the onboarding process and incentive structure of your first give salespeople has ripple effects that will be felt for a long time in your company (or a short time if you mess it up.)

I'd love to hear about tips, good resources, and experiences from early sales team members of startups. Who is in the process of building a sales team now? Who has built the best sales teams in NYC? What did things look like for the first three salespeople?

Why Your Startup Needs a Sales Methodology

Why Your Startup Needs a Sales Methodology Bothsidesofthetable Jun 13, 2013

This article originally appeared on Inc.com Like most startup entrepreneurs, when I began my first company in 1999 I had no formal sales experience. I did have the wherewithal to visit potential customers and try to understand the pain points…Read more ›

Here’s What’s Driving Collaborative Consumption and Where the Market May Head Next

Here’s What’s Driving Collaborative Consumption and Where the Market May Head Next Bothsidesofthetable Jun 9, 2013

I spoke this past week at the LeWeb conference in London, which was a superbly well run event with a very quality production team. Kudos. The 20-minute video of my presentation is here if you’re interested. And it was convenient…Read more ›

12 Unconventional Interview Questions Entrepreneurs Should Ask

12 Unconventional Interview Questions Entrepreneurs Should Ask Onstartups Jun 5, 2013

Where potential employees are concerned, obviously skills are important. Yet we’ve all seen fabulously talented individuals become a team that was far less than the sum of its parts.

While expertise is important, cultural fit can be just as – if not more – important. It's something we obsess over at my company, result in what we call our Culture Code (that describes how we think about talent and culture at HubSpot).

As a result your interviews should focus on more than just skills and qualifications. You also need to ask questions to probe whether candidates will fit into your organization: Are they likely to play well in your particular sandbox? Will their work style and personality complement your team?

Will they not just survive but thrive in a fast-paced, often-chaotic startup environment?

Do your homework before the interview and you should already have a good sense of whether the candidate has the right blend of skills and experiences to be able to do the job well. So definitely dive deeper into an exploration of talent and expertise, but also ask questions to determine whether the candidate can do the job well in your organization – because hiring even one employee who doesn’t fit your culture creates a culture debt you may never pay off.

Keep in mind how the candidate answers is important, but the conversations that follow– since a great interview is a conversation, not an interrogation – can reveal even more:

1. “What concerns do you have about our company?”

Strange question? Not really. No company – and no job – is perfect for any employee (even its founders.) Every company and every job has its challenges and potential downsides.

The candidates you want to hire don’t think your company is perfect; they’ve done sufficient research to know that while yours is not the perfect company and the job is not the perfect job, yours is a company they want to work for because they can thrive, make a difference, develop and learn and grow and a [...]

Why Startups Need a Well Articulated Strategy (And How to Think About Yours)

Why Startups Need a Well Articulated Strategy (And How to Think About Yours) Bothsidesofthetable Jun 4, 2013

I recommend you read Fred Wilson’s recent blog post about the need for a well articulated business strategy before pushing a particular business model. Since Arrested Development is back I thought I’d resurrect Gob Bluth’s answer when he was told…Read more ›

No Phone with Food Thisisgoingtobebig Jun 10, 2013

The other day I went to dinner with a friend. My phone was low on power--drained from listening to the Mets take 20 innings to lose a game. I plugged in before we went out.

When we were ready to go, I instinctively reached for my phone, because I never really walk out the door without it. We weren't going far, but that wasn't the point. It has become an appendage--a tether to the rest of the world, preventing me from straying too far from the other billions.

For some reason, I stopped. I realized that all I was doing was heading out to eat at a new place I was excited to go to for the first time and to catch up with a good friend. Neither of these tasks--eating, listening, talking, required an internet connection, let alone a phone. I decided to leave it.

"No phone with food," I said.

We ate at Bar Corvo. The food was terrific. Get the chicken--it's incredibly tasty. I focused on my friend across from me. An interesting byproduct of not having the phone on me was that there was a little extra incentive to maintain a good conversation. I couldn't supplement it with a wikipedia search for the official definition of "gratin" or a private viewing of the day's Instagram photos. I had to be fresh, original, and thoughtful. It was Humans Unplugged and it was really nice.

I think that's going to be the rule from now on--no phone with food--and I think I'm going to like it.

NYC: Regulatory nightmare for tech startups trying to conduct consumer friendly businesses Thisisgoingtobebig Jun 5, 2013

New York City is a fantastic place to live--I've been here all my life. I wouldn't want to live anywhere else.

That being said, it isn't necessarily the easiest place to live, but it's worth it.

That's why I get excited when companies in my industry create businesses that improve the living experience of being here. The mobile phone has the potential to be incredibly transformative for the lives of NYC residents.

So when the city government seems to be bending over backwards to make tech companies want to start and grow their businesses here, conducting business here might be another story. Companies that make people's lives easier, should they run into entrenched Big Apple interests like housing and transport, aren't finding that NYC is as easy a place to offer their services to NYC residents.

Remember the on again, off again Uber and Halio taxi fiasco? Hailing a ride using your phone in NYC has had more hiccups, false starts, and court filings than you can shake a Citibike at, and I'm sure it's likely to continue. Ride sharing service SideCar was recently the target of a NYC police sting that resulted in two cars being impounded--cars belonging to drivers in their network offering rides to people.

Gone are the days of stepping out onto the road and offering up a thumb, because what you might get back from the city is a finger.

Government served an incredibly important role regulating ground transportation in the past. Oversight prevents outer borough price gauging on behalf of car services and abuse of unsuspecting tourists who don't realize that LGA is closer to the city than you think.

But do we need government playing the same exact role when loosely constructed networks can serve that same purpose. A bad Uber or Sidecar driver will never get another ride--and user side data can instruct people what they should expect to pay before they get a ride. It's not an accident that Uber drivers are some of the friendliest, nicest folks you'll ever [...]

Come Check Out a Very Important LA Tech Event on June 1st

Come Check Out a Very Important LA Tech Event on June 1st Bothsidesofthetable May 31, 2013

Tomorrow LA is hosting an important tech event - please consider registering and coming by. A special thanks to Jason Lehmbeck, founder & ceo of DataPop, a great LA startup of which I have been a long-standing fan, for championing this…Read more ›

What Would it Look Like if Elon Musk Pitched a VC Today?

What Would it Look Like if Elon Musk Pitched a VC Today? Bothsidesofthetable May 30, 2013

This week I attended the All Things D Conference in Ranchos Palos Verdes. It is always a stellar event. The good and great of the tech industry were there: Tim Cook, Sheryl Sandberg, Dick Costolo, Max Levchin, etc. But Elon…Read more ›

New college grads: Don’t sell your time for a living

New college grads: Don’t sell your time for a living Andrewchen Jun 3, 2013

If there’s one thing I could tell every graduating student, this is what I’d say: Jobs suck. At least the traditional version of a job, in which you do something you sorta hate, from 9-5p, and are paid for your time to just grit your teeth and do it. Let’s call this the “sell your [...]

8 Tips To Get the Most Out of Your Investors and Board

8 Tips To Get the Most Out of Your Investors and Board Bothsidesofthetable May 28, 2013

Rob Bailey is the CEO of DataSift. He wrote a post this long weekend on how he manages the board of DataSift. You should read it. In his post he asserts, “You get the VCs you deserve” and the corollary…Read more ›

What Playing Dots Can Teach You About Startups Thisisgoingtobebig May 31, 2013

I don't need to explain what Dots is, because you're already playing it. Don't lie.

In fact, you're playing it so much, that it better teach you some lessons as a founder, otherwise, it's probably distracting you from your startup.

Here's a list to defend your high score from your investors:

1) Reset the Board: Don't fall in love with your first idea. Find the best possible starting point to create momentum.

2) Expanders: Eliminate as many features and possible directions right away. Clear the board of all the dots of one color in the same way that you focus on less things in your startup to do them better.

3) Buy some time: Raise a little more money than you need because cash (time) always runs out at the worst possible moment.

4) Don't look at the leaderboard: Other people will be dramatically more successful than you--to the extent whether they've discovered a cheat or are playing a different game altogether. Don't worry too much and focus on your own game.

5) Just make squares: It's tempting to go for rectangles, but squares get you all the points you need. Just focus on what you need to move your company forward each day. Great startups are a series of small victories, not giant, pointless wacks at making a lot of noise.

6) Shrinkers: Get stuff off your plate when it's in the way. It's easy to work on just the things you like to do, but focus on what's really holding you up and tackle it head on. Eliminate the dots that are directly in your path to making a square.

7) Stay calm: If you start freaking out when things are starting to go your way, or not going your way, you won't be able to focus. It's a marathon, 65 seconds at a time.

8) Don't freeze: Keep those fingers moving. There's always something you could be doing--reaching out to one more customer, eliminating one more dot. You don't have a lot of time, so idle time can kill you.

9) Know your next move: The moment your thumb hits the screen, you need to be looking elsewher [...]

Teach 'Em to Tinker Thisisgoingtobebig May 28, 2013

The other day, I took part in a forum about technology education in Brooklyn. So much of the focus was on how to produce usable software developers inside the four walls of a classroom. There was a CTO in the room who had a fifty plus person tech team and so I asked him, "How many of your developers learned their trade in the classroom versus being essentially self taught?"

Answer: All self-taught. Not a single one of his developers came out of school as usable commercial software developers.

And yet the number of software developers in NYC who work at startups has probably grown tenfold in the last eight years, leading me to ask the question of whether or not putting code in the classroom will make the biggest impact on innovation in our community. It's an especially relevant question for me as I've recently joined the board of the Bronx Academy for Software Engineering, one of two software focused high schools in NYC.

Don't get me wrong--I think software literacy is extremely important. Whether or not you decide to actually write code for a living, understanding how computers work and what they're capable of will be a life skill going forward. My biggest question is how you get the biggest bang for the buck educationally, based on what we can observe in real life.

Software languages evolve more quickly than schools could ever change their curriculum--so it seems somewhat problematic to hard code a set of learning goals when industry requirements are so fluid.

That's why I think the main goal of any educational endeavor whose goal is to produce engineer should be focused on what they inspire kids to do *outside* the classroom--we should be teaching them to tinker. If we can't inspire kids to learn when they leave the classroom, they're never going to pick up software development as a lifelong pursuit.

The computer titans of today grew up building computers--coding up programs not in a classroom, but at home or in libraries. In fact, many of them d [...]

As Populist as it May Feel, 98% of VCs Aren’t Dumb

As Populist as it May Feel, 98% of VCs Aren’t Dumb Bothsidesofthetable May 26, 2013

By now you will likely have read Andy Dunn’s scathing post about Venture Capitalists in which he decries the industry’s masses. I read Andy’s post with a knowing smile on my face. After all, I am no stranger to the publicly expressing…Read more ›

14 Revealing Signs You Love Your Startup Job

14 Revealing Signs You Love Your Startup Job Onstartups May 23, 2013

You may not be frequently giving out an embarrassingly gushing smile and you might not write little love notes during your lunch break. But, there are ways to tell if you love your job.

Of course, no job is perfect -- even the best of relationships have their down days. We all have to do things we don’t like. I love working at HubSpot, it's the best job I've ever had (but, that's by design). But, even I have “off” days where I'm not spending all my time doing things I absolutely love.

So all of the following may not be the case all of the time. But when you love your job, many of the following should be the case much of the time:

1. You don’t talk about other people; you talk about the cool things other people are doing.

“I hear Michelle has really improved our customer happiness scores.” or “I’d love to know how Mike managed to rescue that sale.” “Sherry developed a new tool that's made our lives so much better.”

When you love your job you don’t gossip about the personal failings of others. You talk about their successes, because you’re happy for them – and because you’re happy with yourself.

2. You think, “I hope I get to…” instead of, “I hope I don’t have to…”

When you love your job it’s like peeling an onion. There are always more layers to discover and explore.

When you hate your job it’s also like peeling an onion – but all you discover are more tears.

3. You see your internal and external customers not as people to satisfy but simply as people.

They aren't numbers. You think of them as real people who have real needs.

And you gain a real sense of fulfillment and purpose from taking care of those needs.

4. You enjoy your time at work.

You don't have to put in time at work and then escape to life to be happy. You believe in enjoying life and enjoying work.

When you love your job, it’s a part of your life. You feel alive and joyful not just at home – but also at work.

5. You would recommend working at your company to [...]

The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary

The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary Bothsidesofthetable May 15, 2013

No. The one word the best entrepreneurs never accept. I said it. Now let me walk you through a broader story because avoidance of the word in and of itself will seem cliche. Stay with me. When I was little…Read more ›

The Corrosive Downside of Acquihires

The Corrosive Downside of Acquihires Bothsidesofthetable May 13, 2013

For the past 5 years or so Google, Facebook and a handful of tech industry giants have been quietly buying scores of early-stage startups for their talent. And to keep up with the Jones’s it seems that Yahoo! has now…Read more ›

Get Your Money for Nothing and Your Bitcoins for Free Thisisgoingtobebig May 13, 2013

Land grab.

That's the term that Fred Ehrsam, founder of Bitcoin startup Coinbase, used to describe the current state of play in the Bitcoin ecosystem.

It's an interesting term, one that a) makes me uncomfortable as an investor and b) I'm not sure totally applies to a marketplace that is all about decentralization and openness. First of all, it's a real estate term, obviously. It applies to a finite, physical resource. As the saying goes, "They're not making more land."

When and where do land grabs happen? Shifts in population, transportation, and economic opportunity produce land grabs. Settlers in the Western United States in the 1800's participated in land grabs. The more real estate you could secure, the better off you were--sort of. Technically, there's only a finite amount of land in Wyoming, but there are so few people there, it's priced as if it was pretty abundant. You could claim a whole bunch of land. However, the land itself had more value in terms of what it enabled you to do rather than having some inherent transactional value in a marketplace--because it was so abundant. Even today, land in the middle of the country is still pretty much dirt cheap--but if you decided to be a rancher on your land, you could probably scratch out a living. Contrast that with Williamsburg in Brooklyn eight or ten years ago. Anything you bought could be flipped now for multiples of what you paid for it--regardless of whether or not you developed it. That's because there's a finite supply of land within a certain amount of subway minutes from Manhattan. There's only N number of plots that are walking distance to the Bedford stop on the L. Increased demand, finite supply, price goes up.

Is there a North Brooklyn real estate bubble? It's entirely possible. We've certainly witnessed recent real estate bubbles before--but they tend to be more pronounced in places like Nevada and Florida where there seems to be tons of land AND tons of excitement about that land. Exci [...]

Why Online Video Just Took One More Big Step to Legitimacy

Why Online Video Just Took One More Big Step to Legitimacy Bothsidesofthetable May 8, 2013

Anyone who reads this blog frequently will know that I am a big believer in low-cost video content and specifically the power of YouTube as a content creation & distribution platform. Our industry just took one big step towards legitimacy with the…Read more ›

The Pitch Deck We Used To Raise $500,000 For Our Startup

The Pitch Deck We Used To Raise $500,000 For Our Startup Onstartups May 8, 2013

One of the big no-no’s we’ve learnt about early on in Silicon Valley is to publicly share the pitchdeck you’ve used to raise money. At least, not before you’ve been acquired or failed or in any other way been removed from stage. That’s a real shame, we thought. Sharing the actual slidedeck we used (and one, that’s not 10 years old) is by far one of the most useful things for others to learn from. In fact, both Joel and I have privately shared the deck with fledging founders to help them with their fundraising. On top of that, our case study is hopefully uniquely insightful for lots of people. Here is why:

Half a million is not a crazy amount: It’s therefore hopefully an example that helps the widest range of founders trying to raise money.
Both Joel and myself are first-timers: We couldn’t just throw big names onto a slideshow and ride with it. We had to test and change the flow and deck a lot.


Ratio thinking
One of the most important elements, that we had to learn during our fundraising process was the concept of “Ratio thinking”. Jim Rohn, the famous motivational speaker, probably explained it best:
“If you do something often enough, you’ll get a ratio of results. Anyone can create this ratio.”
It sounded simple enough as a concept to us, but man, this was one of the toughest things to learn. Here is how Joel described it in a recent article on ratio thinking:
“The law of averages really comes into play with raising investment. Overall, we probably attempted to get in contact with somewhere around 200 investors. Of those, we perhaps had meetings with about 50. In the end, we closed a $450k seed round from 18 investors. Perhaps the most important part of our success in closing that round was that Leo and I would sit down in coffee shops together and encourage each other to keep pushing forward, to send that next email asking for an intro or a meeting. In many ways, the law of averages is the perfect argument that persistence is a crucial trait of a fo [...]

Linkedin, Facebook, Google, Twitter, eBay, YouTube, Wikipedia, Amazon, Hotmail, Blogger, Apple: How they used to look

Linkedin, Facebook, Google, Twitter, eBay, YouTube, Wikipedia, Amazon, Hotmail, Blogger, Apple: How they used to look Andrewchen May 13, 2013

This is an oldie but a goodie I had to share again- here are some screenshots of early web products, some close to their inception, some a couple years later. If you have some other screenshots of early products, be sure to tweet me at @andrewchen and I’ll try to put them up.

The critical metrics for each stage of your SaaS business (Guest post by Lars Lofgren of KISSmetrics)

The critical metrics for each stage of your SaaS business (Guest post by Lars Lofgren of KISSmetrics) Andrewchen May 6, 2013

[My friend Lars is a product marketer at KISSmetrics and loves helping SaaS businesses understand how their business is growing. He writes regularly for the KISSmetrics blog and his personal marketing blog. He wrote the following post about SaaS products and the metrics you use to evaluate their success level. Lots of great information in there. [...]

The Importance of Proprietary Deal Flow in Early-Stage VC

The Importance of Proprietary Deal Flow in Early-Stage VC Bothsidesofthetable May 4, 2013

When I was new at Venture Capital I was trying to figure out the business. It was a fun period for me because everything was new and I was curious. What kind of deals should I be doing? What stage?…Read more ›

Why Communication with Investors is Important Thisisgoingtobebig May 6, 2013

Board meetings are a pain in the ass.

Unless you're a well funded, growth stage company that has lots of hands on deck--tons of instrumentation that easily dumps out pretty charts and metrics, or luxury amenities like, well, time, most entrepreneurs probably feel like they could be doing more productive things than telling their investors what they did last month.

Same goes for update e-mails. "Frankly, this company is duct-taped together and will be for quite a long time, and shit hits the fan just about every day. Just the fact that we're still here is a major accomplishment, but now we've got to write a rosey little story about how things are great." When stuff is actually bad, you need to find a way to say it without freaking everyone out--and in the grand scheme of things, does it really matter? Shouldn't we just mail you a check in a few years if it works, and let you know when it's a tax write-off if it doesn't?

Obviously, investors might have a few issues with that--for obvious reasons. But, why then, other than "Because we want to know what's going on," should entrepreneurs make investor communication a priority?

1) Good Investor Communication Saves Time

When you have some kind of consistant methodology--metrics you track each month, a meeting that is already booked, a repeat call scheduled, you actually take less time than dealing with individual investor queries one at a time. Investors are less likely to ping you with random stuff when they feel well informed on a consistant basis. So, from a purely selfish perspective as an entrepreneur, if you really want to deal with investors less, you'll setup a good communications strategy.

2) If Investor Communication is Too Hard, Perhaps Your Management Process is Broken

If answering questions and coming up with a review on how things are going feels like reinventing the wheel, perhaps you haven't built in all the management structures you really need to run the business from a well informed [...]

The Damaging Psychology of Down Rounds

The Damaging Psychology of Down Rounds Bothsidesofthetable May 5, 2013

Yesterday I wrote a post about “proprietary dealflow for VCs.” In the article I discussed the downside of raising capital at a too high of a price and referred people to a previous article I had written encouraging founders to…Read more ›