How To Make It as a
First-Time Entrepreneur

How to Make it as a First-Time Entrepreneur

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

After about 6 months of struggling to get something off the ground, I realized a sobering truth: I had no idea what I was doing.

My startup instincts were terrible.

So, I went on a mission to learn from others.

And while “saved our startup” may seem dramatic, it really isn’t. Each of these books has a significant impact on how we approached a key area of our startup.

I honestly don’t think Yipit would be where we are today had we not learned their lessons:

  • Never Eat Alone – I used to hole myself up in my apartment thinking that an hour spent working was always better than an hour spent meeting someone else. This book convinced me I was wrong. I started getting coffees, breakfast and dinners with other founders and potential investors and I was consistently amazed by how much a single 30-minute conversation could cause us to completely re-evaluate our strategies.
  • Influence: The Psychology of Persuasion – So much of startups is getting your users to take certain actions. Getting them to sign-up, share a link, try out a product, etc. Constantly improving the conversion rates of each of these actions is at the core of what most startups do. This book laid out 7 key principles that will help you increase those conversions. Once I read this, I started seeing how every successful company uses them. These principles don’t replace a good product, but they can make it so that more people give your product a chance.
  • Getting Real – Like most other first-time founders, I could get lost in all the potential problems and corner cases our product would struggle with. This book taught me to ignore that instinct. A passage that really struck home with me was that 37Signals launched BaseCamp without billing because they figured they had 30 days to get billing done. While it seemed insane, it both allowed them to focus on problems they currently had and forced them to build a very simple billing system.
  • The Lean Startup – I think of our startup’s journey as pre- and post- learning about the Lean Startup movement. It completely changed how we approached our startup and I owe much of our success to its teachings. Plus, not only did it help us when we were getting off the ground, it’s helping us today as we apply the strategy to new products at Yipit.
  • Don’t Make Me Think – This is an old book, even when I read it four years ago, but it really taught me to put myself in the shoes of our users. It taught me that if the user can’t figure something out, it’s my fault not their fault. It taught me about simplicity and calls to action and re-using existing user interface design patterns.
  • Django Book – I’m not sure this is still the best way to learn Django anymore. But, when I decided to teach myself to code, this online book showed me how easy it could be to build web prototypes. I couldn’t believe how powerful a framework Django was and, within months, we were building and launching our own prototypes. This was the single biggest step-function change for our startup.
  • Startup Metrics for Pirates – Lastly, while not a book (though it should be), Dave McClure’s framework for thinking about startup metrics is brilliant. I found a video of him online giving his talk. Despite it’s terrible recording, I watched it twice, back to back– it was that good.

And, while you may think that reading a whole book about these concepts may not be a good use of your time, keep in mind that the challenge isn’t just finding out about these concepts but absorbing them.

Sometimes you just have to read 100+ pages to finally stop stubbornly following your misguided instincts, I had to.

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

  • cabhishek

    Nice list. I am done with 3 of them 🙂

    • Vinicius Vacanti


  • Sean

    Django Book link is going to “Don’t Make Me Think”

  • David

    good list but think Django Book link is incorrect

    • Vinicius Vacanti

      fixed! sorry!

  • Jason Fried

    Thanks for including Getting Real on your list.

    • Vinicius Vacanti

      Thank *you* for sharing the lessons you had learned. Had a huge impact for us.

    • thumma19

      Jason.. Getting Real help us (AwardedMe) team to reduce more than 50% of the work. We stripped out a lot of features that reduced our go-live for beta version  by more than 6 weeks.

  • Hardik Patel

    Good article. Please correct link for Django Book.

    • Vinicius Vacanti

      fixed! sorry!

  • Steve Mieczkowski

    These are all great suggestions, thanks for sharing.

  • Sunwoo

    I just started to teach myself to code(ruby on rails) around 6 months ago and I’m having a lot of trouble.  I want to be able to go into the city and talk to my prospective customers, but I don’t have a job and I don’t seem to have the technical capability to become a junior level developer in a startup(aka no money).  Should I concentrate on learning to code – getting a junior developer job – Learning to code some more at work – then working on my idea part-time?; or should I get a random part-time job – continue learning to code by myself – and work on my project when I’m not working? Thanks for anyone’s advice!

    • david payne

      I would suggest you to build your own product or something, just v1 prototype of it in ruby on rails and then go meet some potential co-founders or investors.

  • madoublet

    It is a good list, but a serious questions…how are you using the advice in these books?  I went to, selected my city, then bailed when I saw that you needed my email to see deals.  I was not at all persuaded to continue because I had not yet gotten anything out of your site.  And, if anything, you made me stop and think “do I really care enough to go through a registration process?”  

  • Daniel Wayne Armstrong

    Interesting list! I found “Lean Startup” valuable and am currently working through the ”
    Build. Measure. Learn. Lean Startup SXSW 2012″ series of videos on udemy.

  • Ernesto Tagwerker

    Hey Vinny! Cool, I’ve added Influence and Never Eat Alone to my list. What about “4 steps to the epiphany”? I’d expect it to make it to the list. Just wondering why you didn’t find it so crucial.

    • Vinicius Vacanti

      It was important in that it got me thinking about Lean Startup but the book is so tough to read that I don’t really recommend it

      • Ernesto Tagwerker

        Makes sense.

  • paramendra

    Nice list.

  • Maria

    You really are an inspiration. Especially for being able to persist in the face of adversity (something which I am horrible at, I tend to quit very easily).

    • Vinicius Vacanti