Wednesday, December 21, 2011

11 Things I Learned in 2011: Part I

2011 was a crazy year. In the last 12 months, I've had three jobs, launched a tutoring service, started an internet company, hired my first employee, learned to snowboard, visited 8 countries and been sky diving twice.

My current company, InstaEDU, is preparing for an Alpha launch in January. As I think about all the crazy things I expect to learn in 2012, I can't help but be stoked about what I got out of 2011.

There are tons of entrepreneurs out there that can offer far better advice than I can, but here are some tidbits I've learned, both from the early stages of entrepreneurship and from life as a 24-year-old. I'm writing for personal reflection more than anything else, but hopefully someone will find one or two of my observations useful.

1. It's okay - even good - to start small.
My brother Dan and I took an unconventional approach to starting InstaEDU - primarily because we had no idea that we wanted to start InstaEDU; we just wanted to start something. Knowing a little bit about the market, we launched a tutoring company called Cardinal Scholars with our free time. (At this point, I was working at Google.) We paid a freelancer in LA $600 to build a 1995-esque website and hired 14 tutors from Stanford.

Nine months later, we'd done six figure sales, expanded to two new cities, and most importantly, learned a shit ton. We never wanted to build a brick and mortar business, but the experience proved invaluable. From a business perspective, we learned many of the nitty gritty details that come with running a business - incorporating, working together, hiring, customer acquisition, salesmanship, financials, etc. From a market perspective, we had exposure to the needs and wants of hundreds of tutoring customers. We noticed huge holes in the current tutoring landscape, and from there, InstaEDU was born.

While starting two separate companies may not be the best path for everyone, I highly recommend (1.) Working on a project with your cofounder(s) before jumping into a full-blown company and (2.) Getting to know people who fit your target customer profile before building anything.

2. It's not about who you know; it's about what they know.
There are tons great resources out there on entrepreneurship, but nothing compares to being able to pick the brains of those who have recently faced your challenges. I am incredibly fortunate to know a number of very smart and often successful entrepreneurs, all of whom have been generous with their advice when asked. I'm far more confident about raising money after finding out why someone chose convertible debt over equity (and vice-versa), hearing actual questions that investors asked in meetings, and having our deck critiqued by numerous investors and entrepreneurs.

I have the added benefit of dating an entrepreneur who has more experience than myself. Besides being a constant source of advice and knowledge, he's someone outside of the company who understands it well and can bounce ideas around with me.

I would strongly recommend that anyone starting their first company buy a drink for every entrepreneur, investor and mentor that they have a connection to. (I'm quickly learning that there are very few people in Silicon Valley who will turn down a beer.)

I'm not going to recommend replacing your doctor girlfriend/boyfriend with a techie, but going to some events and making a few more friends in the industry certainly couldn't hurt.

3. When you can't hire great people, copy great people.
Ideally your company will have all the engineers your heart desires, a stellar marketing team, witty PR, great product managers and inspired designers. Unfortunately no early startup has every resource.

When I first started working at Nextdoor, we needed a landing page but didn't have a designer. One of the cofounders asked me to take a shot at it. I had never designed anything before and my first attempt was horrific. (Art has never been my forte.) She then gave me a great piece of advice: if you don't know how to do something, just copy those that do.

I found a homepage that I liked (Mint) and put together a landing page with very similar elements. It was certainly no masterpiece, but it worked and it went up on the site. (It's since been redone by a kickass designer.)

This can be applied to all sorts of things. Get inspiration from another company's job description. Look up which API's similar websites use. Instead of paying a lawyer, edit a friend's employment contract.

4. A lot of entrepreneurship is tedious.
Every entrepreneur warns that starting a company is the most stressful thing imaginable. But hey, at least it's exciting - you're innovating, doing new things every day, changing the world as we know it...

What people mention far less often is that entrepreneurship is also tedious. When you're a big-shot CEO, you have employees and assistants at your beck and call. When you're two people trying to get a website off the ground, it's far less glamorous. When I was a marketing manager, I got to focus writing compelling copy and strategically acquiring users. Shortly after starting a company, I was in a dark office, alone, reviewing our terms of service and adding line breaks in the HTML.

I have no advice here. Just know that entrepreneurship is not all product vision and launches and be ready to get your hands dirty. Even when everything is going great, you still have contracts, Excel sheets and expenses due.

5. Working alone sucks.
Some people can pull this off. I quickly learned that I cannot. When I finally quit my day job and went to work for myself full-time, I worked out of my apartment for about a month. (At this point, Dan was back at Stanford.) At first, it was kind of fun - I could go to the gym in the middle of the day. But then I slowly started to go crazy from not having anyone else around. I began working all day at coffee shops just to have people near me. I actually broke down into tears one night for no reason at all. (I am generally not a very emotional person.) As soon as we hired our first employee, I snapped out of it and became a normal person again.

Geographically dispersed founding teams cause enough challenges for new companies. If you do find yourself working solo for a while, I strongly recommend coworking spaces. That will also give you another place to bounce ideas off of people. Better yet, find a way to work together more often - for the sake of both your company and your sanity.

6. Building a company is all about learning on the fly.
The first tech startup that I worked for was Box. At the time, Aaron Levie was 21. As a lowly intern, I thought he had it all figured out. Looking back now, I can see that he was just a smart guy who worked hard and had the tenacity to try things until he found something that stuck.

Since starting my own company, I've had more than one freakout. Suddenly, I realize that there is a ton to do and I'm in way over my head. I've worked for several startups, but there are so many things I've never done before. I've never pitched an investor. I've never built out a team. I've never figured out how to scale a product.

I finally calm down when I remember that there's no way that other 20-something entrepreneurs were born knowing which clauses to negotiate in a term sheet and which payment system is best for an online marketplace. When you're an early-stage entrepreneur, one day you're a lawyer and the next day you're a designer. You're not going to be perfect, but hopefully you're going to figure it out. This is why people say investors often care about teams more than products.

Continued in 11 Things I Learned in 2011: Part 2

You can follow me on Twitter at @ajalison


  1. Very Good. Looking forward to the next post

  2. Sick post! Need to know the next 5!

  3. Great read Alison.

    You mentioned you had experience working with a startup prior to getting your own off the ground. I'm a recent grad (business) and it seems like everybody wants the industry expert with 5+ years of experience years and no one is really willing to trust a newbie grad, esp a non-technical one. I was just wondering if you had any advice on how I can convince a startup to bring on an extra set of hands.


  4. Awesome post. Also in the startup pre-launch phase and can relate to the "alone in a dark room adding HTML breaks" comment. It is still completely awesome to be building something that will matter.

    Keep it up!

  5. I too noticed myself missing co-workers when I quit my job and went full time with my business. I found that going to meetups helped some and some of the time I spent just working from Starbucks.

    Great insight. Thanks for sharing.

  6. I can relate to this as well as a startup founder. I remember those days (and they are still now) doing those line breaks type stuff, reading legal documents and trying to acquire customers. Its not glamorous and rather tedious, and you require an internal drive to keep going. But I believe the things that you learn every day and those tiny glimmers of satisfaction are worth it!

  7. Thanks for the comments all!

    Ammad, I haven't been in your situation before (I had the advantage of starting out as a practically free intern in college) but I think the two most important things are proving that:
    - you're the type of person who can figure stuff out on your own
    - you understand the basics of the tech industry
    Before reaching out to a company, learn as much as you can about their space and their competitors.

    Ask around; I'm sure other people have much better advice. Good luck!

  8. Ammad, are there any of those "build a startup in a weekend" type events in your area?
    If you can attend a couple of them. It's a good way to actually do stuff, rather than learning about theory. As a seconadary benenfit, there is a *VERY* slim possability that the team continues into a startup.

    It is also a great way to see what each "skill profile" does, and possibly find a co-founder. You also get to see what happens; if there is no clear leader, there are multiple leaders, shortage of a particluar skill etc. as each team will form in only an hour or two at the start of the event.

  9. Thanks for the feedback guys.

    Mike - I had a chance to attend Startup Weekend and I'm hoping on attending The Lean Startup Machine later this month. I definitely agree that being hands on is a much better approach. So far that's the only two i've come across here in Toronto, but feel free to email me (ammadshaikh at gmail dot com) if you have any that you recommend.

  10. thanks for this sharing, Alison! Your observations are very useful for me! I also dream to become a great entrepreneur someday. I would also like to meet successful entrepreneurs like Yuri Mintskovsky or Mark Zuckerberg. They are great role models! We can learn so many important things from them!

  11. Few years late but i must say, I took some inspiration from Mint as well for my start-up