How To Make It as a
First-Time Entrepreneur

A few days ago, Facebook Co-Founder Dustin Moskovitz said that Y-Combinator’s “No Idea” round for entrepreneurs is “really wrong”.

He further says “the only reason you should become an entrepreneur is because that’s the only way the idea will come into the world.”

What’s funny is that had a young Mark Zuckerberg taken his advice, Dustin might not be a billionaire right now.

It’s not like Mark Zuckerberg dreamed up the idea for Facebook and then turned himself into an entrepreneur to make it happen. Facebook wasn’t Mark’s first project.

He had worked on a bunch of projects from building an algorithm that suggested the next song to play in your mp3 player to a site that compared pictures of people.

It’s not like these were unbelievable ideas that Mark simply had to put into the world. What he had was a passion for solving problems, creating interesting solutions. The skills he learned working on those projects prepared him for Facebook.

And, while some people take the jump into startups because they have an idea that they really want built, the idea itself rarely works.

What keeps them going is that they realize they have a passion for spotting large unsolved problems, creating crafty initial solutions to those problems, building things from scratch, defying the odds, refusing to fail, proving wrong those that doubted them, convincing talented people to help them, fighting off competitors, seeing millions of people use their solution, rewarding those that believed in them and ultimately changing how the world works.

It’s not about that one brilliant idea. Ideas come and go and often don’t seem very magical at first. It’s about your passion for taking an idea, running with it and building off of your progress.

And, so I thank Y-Combinator for helping to dispel the myth that to become an entrepreneur you need a moment of brilliance.

The last thing we need is people convincing smart and talented potential entrepreneurs that they should be waiting around for that brilliant idea.

Those ideas rarely come until someone starts walking down the startup path. And, even when an idea for the next big thing does come, it rarely looks like it.

Things first-time founders regret saying:

• “Don’t tell anyone we’re working on a picture sharing startup. We don’t want anyone to steal our idea.” (If your idea is any good, there are plenty of people working on it. You’re going to win because you out execute them.)
• “Stop the launch! The forgot password recovery email has a typo!” (Stop worrying about the little things and get the product out there. Small flaws like this will have zero impact on your initial success).
• “Our killer feature is that we’ve built every feature you can think of.” (Startups don’t take off because they have tons of features. They take off because they do one thing really well and then expand from there.)
• “Our passwords don’t need to be super secure. But, they should require at least two grammatical symbols.” (You shouldn’t do anything to get in the way of your users signing-up and, unless you’re collecting credit cards or super private information, don’t worry about super secure passwords).
• “We need to launch on mobile web, iphone, ipad, android, windows phone and SMS. But, lets hold off on Blackberry. I want to confirm people like our app first.” (You should just launch on one and iterate till it works before spending a ton of time porting it to different platforms.)
• “We should probably use one of those captchas on the sign-up page. Google uses them.” (Don’t compare yourself to Google, they have very different circumstances than you. You don’t have a spam problem. Don’t get in the way of your users signing-up)
• “We don’t need to talk to users. If Steve Jobs had, they would have asked for a mobile phone with a great web browser.” (You’re not Steve Jobs. Go talk to your users and try to understand their underlying problems.)
• “OMG. I finally came up with our domain name for our picture sharing startup. It’s awesome. It’s… wait for it… pics.com. Hope it’s not taken!” (Almost all good domains are taken. Don’t kill yourself on this. You can always change your domain later.)
• “We’re just like Pinterest but we make the pictures bigger.” (If you’re trying to compete against a heavyweight, the new product has to be 10x better or take a completely different approach.)
• “I would only maybe consider selling our company to Facebook. Maybe.” (Stop worrying about who you’re going to sell your company to and build a great product.)
• “We should never email our users. It’s annoying when sites email me.” (Email is one of the best forms of retention and it’s used by almost everyone because it works.)
• “We will never have advertising on our site.” (Unless you come up with a better business model, you will have advertising on your site but you’ll need a ton of users before it becomes meaningful.)
• “We have to stop using Gmail, Google Docs and Google Analytics. When Google tries to buy us, I don’t want them to see our data.” (The chances this happens are so, *so* remote. These tools are great. Use them.)

First-time reader? Get future posts by subscribing via email or following me on Twitter.

I remember reading the first few pages of Steve Blank’s book, Four Steps to Epiphany, and thinking two things:

• This is not exactly a page-turner
• This is a really smart way of thinking about startups

Soon after, I started attending the Lean Startup meetup in New York and reading Eric Reis’s writings. I was believer.

One of the main principles is to release an early prototype of your idea to potential users to get their feedback.

But, despite being all in on the Lean Startup movement, we didn’t do that.

Why Didn’t We Release an Early Prototype?

Our current idea, Yipit, would find all the deals happening in your city (sample sales, happy hours, retail discounts) and would send you an email with the best 7 based on your interests and your locations.

It would have taken us just a week to have launched an early prototype.

We could have measured success based on whether people opened and clicked on the emails. We could have manually created the emails with deals we found and used MailChimp to send them out. There was no need to build any tech infrastructure.

But, we came up with all sorts of excuses why we just couldn’t release an early version.

Six painful months later, we finally put out the product. It didn’t work which was okay. What was not okay was realizing that our excuses for not releasing earlier were all wrong.

The Excuses We Came Up With

The bright side is that, 6 months later, when we iterated Yipit into a daily deal aggregator, we learned to ignore the excuses and released a prototype in 3 days that took off right away.

Below are the excuses we had and how we realized they didn’t matter:

• It wasn’t good enough yet. We thought manually sending deals wasn’t good enough. We were guessing and didn’t really know. It turned out that six months later, the automated version full of features wasn’t good enough either. We could have learned why it wasn’t good enough 6 months earlier and spent that time actually trying to fix it. Instead, we just guessed why it wasn’t going to work and guessed wrong.
• We didn’t want to give a bad impression to those early test users. I can safely say that this doesn’t matter. Those early test users just don’t care. After we re-launched as a daily deal aggregator, we got exactly one email from a user saying they missed the sample sales. That’s it. In fact, many of those early users enjoyed seeing our product develop.
• It needed these extra features. We thought we had to have a web view, people had to specify where in the city they lived, it needed to have links to the source of where we found the deal. None of these were right. We were guessing. Had we launched in a week, we would have quickly realized these features weren’t going to make a difference.
• It was going to take us a few months to build the tech back-end. We shouldn’t have built it. We should have just used MailChimp to send the emails. For the next iteration of Yipit, we didn’t build the back-end. Users don’t know what your tech back-end looks like. Focus instead on getting the user experience right.
• It needed to scale to accomodate hundreds of thousands of users. No, it didn’t. We weren’t going to get hundreds of thousands of users. Not anytime soon. We should have just been worrying about getting our first 1,000 users.
• Someone will see what we’re doing and copy it. If our idea had any merit, then there would have been at least 10 other groups of people out there also actively working on it. In fact, there were many groups of people working on a daily deal aggregator. But, because we launched in 3 days, we were the first ones and got most of the press attention.
• A potential investor will see it. I’m not sure if an investor actually did see it. But, even if they had, it’s not a bad thing. Investors like to see the progress you make as a product and as a team.
• TechCrunch will write about us when we’re not ready. They won’t. We spent a bunch of time trying to get people to write about us and they didn’t. Also, in some crazy scenario where someone writes about our terrible prototype, I can safely say it won’t matter in the long run. Startups succeed because they have a good product and not because they got good launch PR.

First-time reader? Get future posts via my RSS feed, following me on Twitter, or subscribing via email. Hope you enjoy the posts!

One of the hardest decisions you have to make, as an entrepreneur, is deciding when to give up on your current struggling project. It’s made especially difficult because you always seem to have an exciting new idea rattling in the back of your head.

The difficulty of the decision is further exacerbated by:

• Conflicting accounts from previous startups. On the one hand, you hear about how AirBnB struggled for years before finally making it. But, then you also hear how the founders behind Stickybits, after struggling for almost a year, dropped the project and built Turntable.fm.
• Sunk cost. You’ve spent so much time on your current project, can you really walk away now? Do you want to tell your friends and family that you’re, yet again, starting on a new project? Do you want to admit you “failed” again?
• New ideas seem better than they are. Your new idea is in the “informed pessimism” stage. It probably has all sorts of complications you haven’t thought about.

What if you quit right before your startup was about to take off? What if that other idea in your head is your Turntable.fm?

You Need a Framework

With such an emotional decision, it’s best to try to be as systematic and rational about it as possible.

The key to making this decision comes down to: (1) quickly iterating the product based on learnings and (2) consistently measuring each iteration based on a defined success metric.

Since things like frameworks work better with examples, I’m going to imagine I had the idea for TaskRabbit, the app where you can post tasks for people to do at a price, and that I was just getting started with the idea and struggling.

Defining a Success Metric

There are many possible success metrics and it depends on your business.

One of the more popular generic success metrics is the net promoter score. Basically, the score tells you how likely your users are to recommend your app. If the majority of your users aren’t “promoters”, you’re not going to make it. For more on this metric, see Eric Ries’s excellent post.

Here’s the net promoter score of some well-known apps:

But, you can use almost any metric like:

• Conversion rate of people who, after clicking on a facebook ad, create an account after demo-ing your product
• Percentage of people that invite friends on your “invite” friend step after they’ve used your product
• Percentage of people that return to the site a week after signing up
• If you are selling something to consumers or businesses, then your success metric is percentage of people who agree to pay for the product

For my fictitious case study (TaskRabbit), I would go to craigslist and find people asking for help and tell them they should put their request on my new site TaskRabbit. My success metric would be the percentage of people who added the task and perhaps, after putting the task up, I would give them a net promoter score survey.

With my success metric defined, I’d be ready to start iterating.

Why You Need to Iterate

Where some entrepreneurs stumble is they are never willing to iterate their product. They have an idea for the product, they put it out, people don’t like it and they throw in the towel. It’s incredibly hard to get it right the first time. You have to iterate.

Other entrepreneurs believe their product will magically work after a while. Unless they are iterating, it’s very unlikely it’s just going to magically take off. You have to iterate, you have to do so quickly, and you have to make sure the iterations are significant.

The changes you need to make must address the fact that your project must not be delivering enough value to the user at the cost you are requesting of them. For example, your emails aren’t valuable enough for them to bother opening. They don’t like it enough to recommend to their friends. They didn’t like it enough to take time out of their day to check it again a week later. In my fictitious TaskRabbit case, it could be that just a few people on craigslist are actually putting up their tasks on TaskRabbit and my net promoter score is negative.

At this point, people will tend to think they have a marketing problem. Not enough people know about it. But, it’s almost certainly that you have a product problem.

Iterating

Before you go trying to fix your product, you should diligently note down where you currently rank your chosen success metrics. You need to make sure you get a big enough sample size to make sure your stats are accurate which can be hard to do by just talking to people in person.

Once you’ve noted your metrics, your goal is to find out why you have a product problem. You need to dig deep into the user psyche and pull out that reason.

You can give people online surveys to take, you can pay people $10 to get on the phone with you and, even better, you can bring in people to talk to you in person (via craigslist, buy their coffee at starbucks, etc.).

In my fictitious case, I finally muster up the courage to find out why TaskRabbit isn’t working. It turns out that potential users don’t trust the people who will be doing the tasks.

So, you go back to your apartment, implement a fix to the problem and release it again.

Compare Success Metrics for Each Iteration

Whatever methodology you used previously, you should do it again with new users and measure where your new product ranks on your chosen success metric.

You may find that your success metric is hugely improved and the product is taking off.

More likely, you’ll find that your success metric improved a little bit, stayed flat, or depressingly gone down.

Regardless, you need to get in touch with these new users and find out why they still don’t really want/need your product. You may find that you didn’t actually solve the problem you thought you were solving.

In the TaskRabbit example, I could have added a small bio next to TaskRabbits to make them seem more trustworthy. But, if the metrics didn’t improve, then I was wrong. I either didn’t actually address their concerns or there were other concerns that I didn’t know about. So, I could do something more dramatic like stating that all TaskRabbits have undergone a thorough background check.

Back to your apartment to iterate again.

Target States

With your various iterations, you’re trying to get to two potential states:

• Success metric takes off. Your product will take off along with it. For net promoter score, it becomes positive.
• Your success metric improvement stalls. You’ve iterated several times and, while they slightly improved your metrics, it hasn’t been enough. You’ve also run out of ideas on how to continue iterating. It may be that people don’t really have the problem you’re trying to solve. Or, the way you’re solving the problem is too demanding on the user and you don’t know how to make it easier for them.

It’s Okay to Start Something New

Hopefully your various iterations will take your project to where it needs to be to take off with your audience.

However, if you are iterating, your metrics aren’t improving and you’ve run out of ideas on how to address your users’s concerns about the product, it’s okay to throw in the towel and start working on a new project. You’ll have learned a tremendous amount from your first go around and will be in a much better position to make your next idea successful.

See discussion on Hacker News.

First-time reader? Get future posts via my RSS feed, following me on Twitter, or subscribing via email.

Hustling from our shared workspace cubicles

“So, what do you do?”

Ugh. I hated that question.

The truth was that we were trying to start a new venture but we hadn’t really made any progress.

But, instead of just muttering something, I would force myself to enthusiastically pitch our current struggling idea. They would nod along but the skepticism on their face was hard to ignore.

And, when I was done, they would sometimes hit me with: “So, is that your full-time thing?” Ugh. What that really meant was: you’re trying to tell me that you spend all your time working on that ridiculous idea?

The Grind

We left our finance jobs in the summer of 2007, and we worked really, really hard. By February of 2010, it had been over two and half years of hustling on no salary. What did we have to show for it? Nothing.

We hadn’t made a dollar of revenue. We had been rejected by every investor we talked to. We hadn’t been able to recruit anyone to join our team. We hadn’t gotten traction with any of our ideas.

We had failed to get more than 10K monthly unique visitors for Yipit for the last two years despite trying several ideas with it. We were going sideways:

On a personal level, my life savings was disappearing. I kept getting hit with late penalties on my credit card. Not because I didn’t have the cash to pay it, but because I just didn’t want to think about it. It was too depressing to look at my depleting bank account that I had worked so hard to build up. I remember withdrawing all the money from my 401K account and having to confirm that I did, in fact, understand the massive penalties I would incur for doing so.

In all honesty, I probably would have given up earlier. The only reason why I didn’t was out of loyalty to my co-founder, Jim, who had also quit his finance job. He had passed up many amazing job opportunities to work alongside me and I wasn’t going to quit on him.

Everything Changes

So, it’s now February of 2010, over two and half years since we started, and we have yet another idea: build an aggregator for the early but quickly growing daily deal industry. The idea was sound, timely and right up our alley since we had been doing local deal aggregation for the last 9 months.

And, in just three days, everything changed.

We launched the new idea in a three-day scramble, got some initial press, users loved it, and four months later raised $1 million from amazing investors. A year after that, we’ve raised $6 million, made real revenue, attracted hundreds of thousands of users, and recruited amazing people to join our team (we’re hiring! join us!). And, best of all, we’re just getting started.

So, what happened in those three days?

I’m convinced that if we had the idea for a daily deal aggregator back in 2007 or 2008 or even 2009, we wouldn’t have gotten traction because we would have messed it up.

But, after two and half years of failing and learning, we knew exactly what to do:

• Product strategy. We had become a part of the lean startup movement. I had gone to the New York lean startup meetups from the beginning, read Four Steps to Epiphany, and knew we just needed to build a minimum viable product.
• Coding the prototype.  I had taught myself web development over the last few years and Jim had taught himself front-end development. We didn’t need to find an outsourcer, we just quickly built it ourselves.
• Designing the user interface. We had already designed a bunch of prototypes. We knew how to design the landing page to collect user email addresses, the sign-up flow to collect preferences and to ask our new users to spread the message.
• Getting initial press. We knew how to craft our story in a way that would get journalists interested. We got featured on TechCrunch and Wired giving us a strong initial boost
• Getting investors interested. We had built relationships with many New York angel investors over the last few years and we were able to quickly drum up some interest based on our traction since they already knew who we were.
• Building buzz. We had become involved in the New York tech community and our friends in the industry really helped us build initial buzz for Yipit

Now that I look back, I realize that I was wrong to think that we had nothing to show for two and half years of hustling. While we didn’t have outward signs of success, we had learned something very important: the art and science of starting a new venture. It took us almost three years to know what exactly we had to do during those three days.

And, so, to everyone out there who’s struggling and feels like they have nothing to show for it, I hope this post keeps you going. You’re learning every day. And, when the inspiration strikes, you’re going to be ready to pounce on it.

Back in November of 2006, before NY Mag and TimeOut put startups on the cover, before the “tech bubble”, before Twitter and Foursquare were popular, before working at a startup in NY was considered a reasonable thing to do, I was a private equity investor for a $1.6 billion fund called Quadrangle Group.

It was just my third year out of college and I made a little over $250,000. For a Brazilian immigrant who spent most of his childhood kind of worried he would have to do physical labor, I felt like I had really made it. My job was challenging (making investing decisions always is) and I worked with some really smart and motivated people.

But, beyond “making it”, I was comfortable. After a year of private equity investing, I felt like I was good enough to do it for the long haul. While I’m sure there would be a few unexpected twists and turns, I sort of knew what the next 20 years of my life were going to be like and it looked pretty good.

There was only one little issue. It turned out that I didn’t really love money.

After 18 years, my mom had successfully passed along an immigrant guilt towards buying anything lavish for myself. So, my expenses weren’t really growing in proportion to my income. And, at least for me, I didn’t see money as a metric of success the same way Warren Buffet does. When it’s all said and done, I didn’t want to be measured by how much money I had accumulated but by what I had built.

But, when you’re making more money than you know what to do with, you tend to procrastinate on any big decisions. Well, at least until you’re reminded of what else is possible.

How I Woke Up

My company, Quadrangle, organized a private conference every year for the media and telecom industry. This was not just another conference, it was ridiculous.

I realized how ridiculous it was when I got an email with the list of attendees. Every major media company executive was coming. Brian Roberts from Comcast, Steve Ballmer from Microsoft, Jeff Zucker from NBC and media celebrities like Katie Couric, Jerry Seinfeld and Harvey Weinstein. While journalists weren’t allowed to cover the conference, Andrew Ross Sorkin, of the NY Times, was given permissions to write-up a quick blurb about the conference.

I was really excited and had barely slept the night before. The dress code was business formal and I walked into the Pierre Hotel wearing my best suit and power red tie.

I soaked in the scene for a few seconds trying to find the first person I was going to talk to. And, then, it hit me. Why would they want to talk to me? They were the heads of major media companies, I was a 25 year-old finance guy. They didn’t want to talk to me, they wanted to avoid me. I wasn’t doing anything important, anything that could impact their companies. They didn’t care about my suit or my power red tie.

So, for the next 30 minutes, I just awkwardly walked around the room trying to listen in on the conversations people were having. When the panels started, I took a lonely seat in the back.

After listening to a few panels comprised of 50+ year-old media executives, the audience was looking forward to the fresh perspective of the next panel on new media.

The two guests were in their 20′s. I almost couldn’t believe that two people roughly my age had been invited to talk in front of all of these important people. And then, even more shocking, they had all of their undivided attention. All of the 50+ year-old media executives were mesmerized, excited and scared of what they had built and what it meant for them. One was Chad Hurley, fresh off his recent sale of YouTube to Google, and the other, wearing sandals, was a still unknown pre-”The Social Network” Mark Zuckerberg.

When the panel ended, media executives came up to them to talk about working together, get advice on their business. I just stood in the background watching.

I was floored.

They were building something. They were changing how the world communicated. And, they had done it in just a few years without raising significant capital to get started. They willed their services into existence.

What was I doing? Could I do what they had done? Could I build something as significant as they had?

Yeah, right.

I had never built a tech startup. I had never even built a website. What did I know about product management, web development, and user interfaces?

I had a high-paying finance job. I was on my way. It was too late. I had no idea what it meant to start a company and the most likely outcome was failure.

On an expected value basis, the obvious decision was to stick with finance.

I was where I should be.

But, as the days went by, I kept thinking back to the conference. A scary idea started creeping into my thoughts: what if I could build something? Wouldn’t I always wonder? Wouldn’t I regret it? Wouldn’t it eat away at me over the years?

And, that’s when I realized that I didn’t actually know if I was good enough because I hadn’t really failed in life (at least not professionally). Most people don’t really fail. We tend to take the job that we think we’ll succeed in. We are hesitant to reach. And, if we do reach and succeed, then we don’t reach again.

The only way to know how good you might be at something is to fail trying it.

And, that’s when I decided it was time to test my limits. It was time to really reach. It was time to quit my safe job and walk straight into almost certain startup failure.

I had no idea how to start a successful tech company, but I was going to try. I was going to step into that arena. And, whether or not I triumphed or got knocked down, I didn’t really care much. I wanted to know the bounds of my abilities.

So, What Happened?

It’s now 4 years since I left Quadrangle. Did I fail? Hell, yes. I got knocked down many, many times. For the first 2 years, I had no idea what I was doing and was just swinging blindly. But, every time I fell, I learned why.

After two and a half years of failure, we launched the third version of Yipit and it took off. We’ve now raised funding twice including the most recent $6 million round this summer. Yipit is growing, we have a strong vision of where we’re going and we’re building an amazing team (join us!).

But, perhaps, one of the sweetest moments was that I was invited to the latest Quadrangle conference. Not as a panel speaker, we’re nowhere near that. But, as part of a session where three startups pitch Barry Diller for 3 minutes and then he grills you with questions in front of the entire audience of media executives. It was clearly terrifying but it went well. At the end of the session, Barry picks the startup he thinks is most like to succeed and he picked Yipit.

When I stepped off the stage, still kind of shaking from the presentation, media executives came up to me talk about what we were working on and how we might be able to work together. I couldn’t believe they were coming to me (and I wasn’t even wearing my power red tie).

How do you know if your startup idea is the next next big thing?

It’s easy. It isn’t.

Most Great Companies Started With Bad Ideas

Most great companies started off with very different ideas that were either not very good or impractical. Very rarely does a startup actually start with the idea that makes them the next big thing.

Here are just a few examples of successful companies that had very different and troubled initial ideas:

• Initial idea: Allow groups of people to band together to accomplish a goal called ThePoint
  • Eventually: Groupon
• Initial idea: HTML5 supported location-based service
  • Eventually: Instagram
• Initial idea: Web-based massively multiplayer online game called Game Neverending
  • Eventually: Flickr
• Initial idea: Compare two people’s pictures and rate which one was more attractive
  • Eventually: Facebook
• Initial idea: People to share photos and get grouped based on locations in an app called Color
  • Eventually: To be determined

At Yipit, our initial idea was a local search site focused on furniture in New York. Today, we are the leading aggregator of daily deals like Groupon, LivingSocial and the 485 others.

What Does This Mean For You?

When you stop expecting that your startup idea has to be the next big thing, you can draw some valuable conclusions:

• Stop waiting for the perfect idea. The perfect idea isn’t coming. You just have to pick a problem you are passionate about and start working on it. Over time, you will evolve your startup into the next big thing
• Your idea isn’t the real value, it’s you. The value lies in your ability to learn from potential customers, iterate based on those learnings. Those iterations will determine whether or not your startup will be successful, not the initial idea
• Don’t worry that your first idea will fall flat. It falls flat for almost everyone. Your idea is based on so many assumptions, it’s bound to be full of issues. Figure out what’s wrong and fix it.
• Get your prototype out there as soon as you can. Don’t spend six months releasing your first prototype. It’s going to fall flat. Instead, get a prototype into the hands of your potential customers as soon as you can. You need to learn as quickly as possible what’s wrong with the idea so you can fix it.
• Don’t write a business plan. Within a month, your business plan will be irrelevant. Instead of spending that time writing a business plan, spend it getting your prototype into customers hands.

Your initial startup idea isn’t the next big thing and that’s okay. Just get out there and start working on a big problem that you’re passionate about and you may eventually turn it into the next big thing.

Getting feedback on early versions of your prototype is crucial to a startup’s success. You’ll learn more the first day a user tries out your product than the previous 2 months you’ve spent thinking about it.

But, aside from getting user feedback, we really benefited from getting the chance to show Yipit to experienced entrepreneurs and investors.

We would often come back from those meetings and make major changes to our initial prototype plans.

But, it’s hard, especially as a first-time entrepreneur, to get their attention. Their time is their most valuable asset and they can’t meet with everyone.

Plus, even if they do meet with you, it doesn’t mean they will spend real time thinking about your product — the kind of time it usually takes to yield breakthrough product and marketing ideas.

So, how do you get their attention? Well, it seems like one answer is to get into TechStars.

TechStars Mentors

This is my first year helping out with TechStars as a mentor and they have been emphasizing that what makes TechStars different from other programs is their impressive list of mentors.

At first, I was definitely skeptical that the list of mentors was just that, a list.

I’ve come to see that the program, spearheaded by David Tisch, does a fantastic job of getting mentors involved.

They organize one-on-one meetings with the various companies in the program and get mentors to pick a specific startup to actively mentor.

I fully realized the power of the program when I get an email from one of the startups asking for feedback on their prototype.

I opened the email and the ”to” field blew me away.

When I had sent a similar email about the first version of our prototype, it was to five college friends, my brother and my mom. His “to” field included:

• Fred Wilson, partner at Union Square Ventures
• Andy Smith, co-founder of Daily Burn
• Michael Galpert, co-founder of Aviary
• Rachel Sklar, Editor at Large of Mediate
• Josh Stylman, co-founder of Reprise Media
• Nate Westheimer, NYTM organizer and formerly head of product at AnyClip
• Eric Friedman of Foursquare and former associate at Union Square Ventures
• Amish Jani, founder and managing directory of FirstMark Capital
• Matt Galligan, co-founder of SimpleGeo
• Jeremie Miller, inventor of Jabber

Seriously?! That’s a ridiculous list of people to send over your initial prototype.

Aside from getting great feedback from them (both on the product and vision), if some of them start using the product in ernest, they could bring many more additional users.

I wish we could have sent Yipit to a list like that.

The good news is that it’s easier than you think to get 1,000 people to try your site.

The bad news is that it’s really hard to get those people to turn into users, users that create an account, users that come back repeatedly and users that tell their friends about your site.

This post is about how to get 1,000 people to try your site so you can find out what isn’t working, iterate and keep trying to build a site that people, other than your mom, actually come back to. I’ll write a future post on how to retain those users.

Get Yourself a Domain Name and a Splash Page

You should set up your splash page today. Not tomorrow, today. In terms of the domain name, it’s okay if you don’t love your domain name; you can change it later though it’s always easier to pick a good one from the start.

Once you get your domain name, you should use a service like unbounce to create a simple splash page. You don’t need a programming background to create this page.

The goal of the splash page is to collect email addresses from visitors. How do you do that? The splash page tells a user very clearly what problem your site will solve for them. If the user submit their email address, you’ll give them early access to the site when it’s ready. For Yipit, the splash page said: “Get All the Best Daily Deals in Your City”. For Tumblr, it’s “The Easiest Way To Blog”.

Those email addresses become your early test users. When your prototype is ready to be tested, you’ll email a portion of these users and get them to test-drive your prototype. You’ll iterate and invite more users from your list till the product works.

Now, how do you get people to visit your splash page?

How To Drive People to Your Splash Page

There is no shortage of ways to get people to your splash page. The following are things we at Yipit did and things we’ve seen our friends do:

• Add Link to Your Email Signature. Seems obvious, but most people don’t do this. You should have your value proposition at the bottom of your email with a link to your splash page. For us, it was: “Get All the Best Daily Deals in Your City: http://yipit.com”
• Add Link to All Your Web Profiles. Add a link to your splash page on your Facebook, Linkedin, Twitter and every other account you have. Now you might see why it helps to be a high profile social media user.
• Create a Demo Video. Even if your prototype isn’t ready, create a demo video of what your prototype will be doing. Dropbox did this and their video appeared at the top of Digg giving them 100,000 email addresses wanting access to their site. You can also add this video to your splash page to help increase conversion of people submitting their email addresses
• Be Full Entrepreneur. When I went to tech events, friend’s drinks, family gatherings, I would pitch everyone on Yipit. Painful, yes. But, it got me good at pitching Yipit and those people would go home and sign-up to check it out.
• TechCrunch and other tech blogs. It will be hard to get press for your site if you can’t give the blogger a prototype to use. But, if you do have a working prototype, this the easiest way to get people to your splash page. For all three of our projects, 140it.com, UnHub.com and Yipit.com, we were able to get TechCrunch to write about us just by submitting it to through their news submission form. If you can give the bloggers some beta codes for their readers, that makes it more likely they’ll write about your site. Just make sure you’re ready for it. If you have a very good demo video, they might be willing to write about you without the prototype.
• HackerNews. HackerNews is a great community of entrepreneurs who are willing to give you good advice on your startup. You need to have a working prototype and let them look at the site directly, though. Here’s some great advice on how to submit to HackerNews.
• Facebook Ads and Google Adwords. This is actually really hard and often pretty expensive. We were never able to really pull this off despite several attempts.
• Start a company blog. The blog should be focused on providing helpful advice on the problem you are helping consumers solve. Kissmetrics, a startup focused on helping websites with analytics, runs an excellent blog on helping startups think through user acquisition. This strategy involves a lot of work so only do it if you have a really good idea for the content you want to create and think that users will appreciate it.

Some final tips and notes:

• Your list will get stale. The longer you wait to invite people to your prototype, the smaller the percentage that will respond to your invite email. You can try to keep the list active by sending them occasional updates on the product.
• I recommend you give the users a survey after they submit their email address where you collect information from them regarding what they are hoping your site will accomplish for them. I have heard good things about surveymonkey
• Encourage users to tweet, share on facebook, or email your site to their friends. One way people have done this successfully is to promise the user earlier access to the prototype if they invite 3 friends.

Now that you know how to get people to your site, I’ll write a future post on what you need to do to make sure those 1,000 people actually stay on your site.

If you have employed any other techniques that have worked well, comment below and I’ll add them to the list.

As a current or aspiring entrepreneur, you should be meeting with a ton of people (potential customers, investors, biz dev partners, employees, journalists).

You will often get introduced via email or you are cold-emailing them.

You are probably excited to meet with them and correctly assume that they are busier than you.  So, like the nice person you are, you want to be as flexible as possible.

And, that’s when you make the mistake of saying: “I’m pretty free the next two weeks, let me know when works for you.”

You may think you are being nice and flexible; but, you’re actually frustrating them.

What you actually just said: “Hey, why don’t you spend some time going through your schedule, pick out some times that work and email them to me. I’ll then sit back and pick one that I like.”

If you really want to be respectful of their time (and you should), your goal is to have them do as little work as possible to get the meeting arranged.

Eric Friedman made some good suggestions on how to most effectively set up an appointment and I’ll reiterate them here with some additional tips based on my experience.

You should do this from the very first communication to reduce the back and forth.

Suggest Possible Times

Go through your calendar and suggest possible days and times that work for you. For instance, I do the following:

The following dates/times (EST) work for me:

Monday, 1/24: 11am – 12pm EST; 2pm – 3pm EST

Tuesday, 1/25: 2pm – 4pm EST

Friday, 1/28: 10am – 12pm EST; 2pm – 4pm EST

Some additional tips:

• The more time slots you suggest the better
• Make sure you specify your time zone (people will assume they are in your timezone)
• The busier the person is, the farther out your suggested time slots should be

Suggest Meeting Location or Phone Number

If it’s a phone call, I always say: “My number is 212-555-0001 but I”m happy to call you.” If you’re trying to set up a meeting with several people, you should get a free conference call number and include the dial-in information.

If it’s an in-person meeting, you should suggest going to their office (confirm their office address in the email) or picking two coffee shops or restaurants (if it’s a breakfast or lunch meeting) that are near their office.

If you do all of the following, not only will the meeting get quickly arranged but, by making it less frustrating for the person you are emailing, it also increases the chances of getting the meeting set up in the first place.

Update: Great comments over at hacker news including another reason to do this is that it suggests you respect your time. I know that sounds like a bad excuse but, unfortunately, appearances do matter.