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.

Since going down the startup path, I’ve made so many mistakes, struggled so many times, failed in almost every way you can.

But, we turned the corner after a few years of hard work. We’re now 25 people (we’re hiring!), raised $7.3 million, and just had our best month ever.

I often fantasize about going back in time and giving myself advice based on what I’ve learned over the last 5 years.

I probably wouldn’t have listened but here’s what I would have told myself:

  • Teach yourself to code. After a disastrous experience outsourcing, you’ll eventually make this decision. I just want you to make that decision today. Of all the things that will happen, this is the single biggest step function change you’ll experience. Also, I know your outsourcers used Perl but please do not teach yourself Perl. Teach yourself Python/Django or Ruby on Rails.
  • Stop holing yourself up in your apartment. You think that an hour spent working is more productive than grabbing coffee with another founder. The problem is that you don’t yet know what to do in that hour. Talking to other founders, you’ll get some valuable advice that will help you save weeks of time. Plus, those founders will eventually introduce you to new hires and investors.
  • Don’t be afraid to talk to potential investors. You keep avoiding it because you know you’re not yet ready to raise funding. While you’re right, you should still meet with them to get advice. Investors want to have a relationship with you and not just shotgun fund you. When you finally do raise a round of funding, it will have been with investors who had already gotten to know you.
  • Stop worrying about PR. You spend too much time thinking about it. Your startup won’t take off because you got great PR. It will take off because you built a great product. PR is a good way of getting some early test users. It’s not how your company will take off.
  • You’re not supposed to know what you’re doing. You keep trying to rely only on your instincts. The truth is, your instincts are terrible. You don’t know what your’e doing and it’s okay. You’ll realize this at some point and go out and get advice. You’ll eventually stumble into the Lean Startup movement. I just want you to do this sooner.
  • Celebrate the small victories. That feeling that you’re not quite where you want to be won’t go away. The way you feel now hoping to get your first 1,000 users, you’ll feel the same way when you’ve raised $7.3 million and have 25 people working on the team. You’ll never be satisfied with your progress so take time to celebrate the milestones.
  • Don’t worry about all the problems you don’t have yet. Focus on the one big problem in front of you. There’s a good chance the other problems you’re worried about either will get solved on their own or won’t be as a big deal as you think.
  • Build your prototype in weeks, not months. You’re going to get lots of ideas. Don’t spend months trying to build a prototype. Build something simple to test out the core assumptions of your idea. In a few years, your prototypes will be built in days.
  • Your first few prototypes are going to fail. You’re going to work really hard on your first few prototypes only to find out that they don’t work. That’s okay because you’ll learn so much that it will make you more likely to succeed with your next prototype. But, what’s not okay, is spending months and months building those prototypes.
  • Lastly, I have an idea for you. When the iphone comes out, build a photo sharing app where you help your users make their photos look better by adding filters. Call it “Instagram”. Trust me.

While I have yet to figure out how to go back in time, I hope others who are just starting out can benefit from the advice above.

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.

  • Fnord

    Looooool: Lastly, I have an idea for you. When the iphone comes
    out, build a photo sharing app where you help your users make their
    photos look better by adding filters. Call it “Instagram”. Trust me.

    • Vinicius Vacanti

      I probably still would have messed it up.

      • Tony Yuan


    • DWF

      “Better” is debateable.

  • philippevdhd

    Thanks for sharing this! Thanks to your blog I’ve been teaching myself how to code instead of looking for an awesome technical co-founder (which is extremely hard to find).

    • Vinicius Vacanti


  • Mike OK

    What’s wrong with Perl?

    • Vinicius Vacanti

      For modern web development, Perl lacks a great framework like Django and Rails.

      • Mike 2

         That might be your opinion but it’s not universally true.

        • mbrameld

          Help us out then, give us a link to a Perl framework similar to Django or Rails.

          • Matthew Shopsin
          • Moosa

            How about Catalyst, Mojo or Dancer?

      • Fred Moyer

        Catalyst. Mojolicious. Dancer. CGI::Application. Poet. Apache::Dispatch. Jifty.

        As a sidenote, you don’t need a framework to make a prototype. Framework wars are one of the reasons prototypes take 10x longer to build than they should.

        • PJ Brunet

           Funny how a guy who just learned to write code 10 minutes ago thinks he can lay to waste decades of code, Perl, the “duct tape” of the web 😉

          • Vinicius Vacanti

            I didn’t intend to disparage Perl. I meant that, for someone trying to teach themselves, I would focus on Python/Django or Ruby on Rails.

  • Eric Clark

    Great advice, Vinicius! Thanks for sharing. Your first point hits home as I’m coming to that realization myself. I know enough to be dangerous (wouldn’t really call myself a programmer), but struggle to know if I’m learning to code the “right” way. Any advice on learning to code?

    • Vinicius Vacanti

      here’s what my friend @innonate when through which I think is great:

  • Your name

    Dear Vincent, if I would dare to give you advice 5 years ago, I would say please stay in touch with friends that you cared about before becoming this big-shot big-star you are right now.

    • Vinicius Vacanti

      Ha. Not a big-shot and, like everyone else, value holding on to friendships.

  • nXqd

    Thanks for your great blog post. I love most of your points but perl was good but not as good as ruby.
    Your decision was not wrong but because ruby is good, with rails it is more complete and become amazing. It helps us create real product fast and ruby on rails has inspired a lot of framework in difference languages, this is too good 🙂

    As a young and passionate developer, I enjoy your post a lot. One day, I hope I can write same lines like yours 😉

    • Vinicius Vacanti

      Definitely don’t recommend learning Perl while trying to build most prototypes.

  • Brett Hardin

    I completely agree with you. I feel like there are wise people (those who learn from others) and smart people (those who learn from their own mistakes). Each one of the points, except the last, is incredibly valuable.

    • Vinicius Vacanti

      Being able to learn from others is a very valuable skill.

  • Song Zheng

    Great Article! I could really use #2. Sometimes I go out but all I can think of is that couple of lines I could be writing to get that new feature out. 

    After coding for a few hours it’s great to go out and get a breath of fresh air.

    • Vinicius Vacanti

      ha. I remember being there.

  • Gordon Bowman

    Great post. Especially like point #2. Getting out of your apartment and talking with other founders helps you flush out your ideas. Better still is finding ways to talk with actual customers. Both help to aim the prototypes and experiments that you build later. And more importantly, give them a better chance for success. 

    • Vinicius Vacanti

      Definitely. Talking to actual customers, especially ones actually using your prototype gives you so many ideas for product improvements.

  • Ben Hebert

    I started learning to code last week and settled on python / django to start. I’m happy to see an entrepreneur recommending that as a place to begin. All the best!

    • Vinicius Vacanti

      I’ve had a great experience with it. Make sure to deploy using Heroku so you don’t have to worry about all the server admin stuff.

  • egranata

    Great post! It reminded me of how inspiring your talk at SXSW last year was. Boy, if I could go back in time, I wouldn’t have let the CodeWarrior C++ Starter Kit intimidate me as much. But after tooling around in HyperCard, it was quite a leap.

    • Vinicius Vacanti

      Glad you liked the SXSW talk! Don’t be intimidated!

  • Guest

    buy Apple stock

    • Vinicius Vacanti

      ha. yes.

  • Moisey Uretsky

    I think a couple of the points touched on this but I’d also say having a great board of advisers early on can be invaluable in getting your startup on the right path.

    We’ve certainly benefited a huge amount from some AMAZING mentors in TechStars like Jason Seats and JP O’Brien.


    • Vinicius Vacanti

      That’s good advice.

  • Mukund

    Good post. What about exercise and keeping healthy?

    • Vinicius Vacanti

      Great point. Would have suggested that as well.

  • Frantzdy Romain

    Nice. I love this one. We took Paul Graham’s advice for launching often and early for and the early feedback was critical to making our product better although we failed hard with the first prototype.

    • Vinicius Vacanti

      it’s rare someone doesn’t fail hard with their first prototype.

  • Look Ma, no hands!

    “Teach yourself to code”  Good idea, its like, you know, having a skill that is valuable to others that you can use to participate in trade? 

    Me, I’m going to make my money from the railroad.  Have I ever driven a train?  Nope.  BUT I have some great ideas on how to drive trains.  Now if I could only find that awesomely talented train driver that doesn’t have his/her own ideas and wants to do my ideas (because after all I am an entrepreneur, and I am an expert in ideas).

    Good luck lasting another 5 years when the investors wise up and stop investing in vaporware.

    • Vinicius Vacanti

      While I see where you’re coming from, the goal isn’t to become a technical co-founder or a long-term contributor of the codebase. The goal is to get enough momentum so that you can recruit great developers that will turn your vaporware into a strong codebase.

      • mrconnorobrien

        I was about to write almost exactly the same thing. The train driver analogy doesn’t hold up here. Knowing how to drive a train expertly isn’t the core skill necessary to start a new railroad. The core skills required to start a company aren’t necessarily the same as the skills required to build or maintain the product or service the company will come to produce – though knowledge of those underlying skills is a definite plus.

        • Look Ma, no hands!

           I guess if your in business for the sake of being in business, then you both are correct.  I feel we have lost the tradition of apprenticeship in the USA and in the technology sector.   The line of reasoning you put forth is the same that Harvard MBA students profess: “I only have to know how to manage, I don’t have to know what I am managing.”  As a great software engineer (IMHO 🙂 ), I say that I don’t need you (i.e. the non-technical co-founder).  In today’s world of bootstrapping by a shoestring, if you don’t have a core competency that is central to the business, then you are just dead weight (and you are probably making the “wrong” business decisions often because of your lack of experience).  So Vinicius, your advice was good: If you are selling software, learn how to write software.

          • Vinicius Vacanti

            Unfortunately, for most new products, when you’re trying to get something off the ground, the challenge isn’t the software development but knowing what to build. That knowhow is product tactics which takes years to develop. 

            The real technical challenge develops later when you have to scale it.

  • Simon Stewart

    Awesome advice, thanks.

    • Vinicius Vacanti

      Glad you liked it!

  • Mememe

    Instagram makes photos look better? HAHAHAHA, Instagram makes them all look like old crap. it’s the most useless app ever

    • Vinicius Vacanti

      So far, seems like millions of people have been finding use out of the app.

    • a_w_young

       Completely subjective. I think a lot of images look better with the pushed colors. Some look unnatural though. I say this as someone who spent a year bitter about it because it mimicked a collection of film cameras and techniques I spent a lot of time and money on previously and didn’t want a bunch of punks thinking they were “artists” by pressing buttons on their iPhone. I’ve since come to the conclusion that it’s just FUN and sometimes you get pretty pictures out of it. Instagram hate is the “most useless app ever”.

  • a_w_young

    When you learned how to code, did you have any previous programming experience at all?

    It’s my most daunting obstacle in things I want to do right now. I understand the principles of programming and have gotten through some of the basics when I was younger (It’s always been around, I wrote simple BASIC games from the age of 3) but I’ve never mastered anything enough to do anything useful at a production level and most modern languages are rich with functions way beyond that of anything I learned over the past couple decades.

    • Vinicius Vacanti

      start with a very simple project. like a website that just says “hello”. you’ll be shocked how easy django and rails + heroku make it.

  • giffc

    great advice as always Vin. The only point where I hear so much conflicting advice about is #3: “Don’t be afraid to talk to potential investors.”  

    The alternative view is that you can waste a huge amount of time talking to investors and it won’t make a difference. If you get hot, they want in. If you don’t, they won’t. So ignore them until you are ready to play the momentum game.I guess I find myself in the middle. There are a few people who’s opinion I respect and I enjoy getting their feedback early, but I wouldn’t canvas too broadly. There are also so few investors in New York that are actually leads.

    • Vinicius Vacanti

      Hmm. I think I agree with your position. Go talk to the people you respect as opposed to just anyone who does investing. The only thing I would say is that I’ve found some younger VCs to be super helpful.

      • giffc

        re: younger VCs, me too — when I was doing Aprizi back in 2010, I got a lot out of talking to Phin Barnes and Sarah Tavel in particular. So there are different conversations — those that can get you funded, and those that make you think better about your business. They are inter-related but different.

  • Nathan

    So what’s the best route to take when learning to code? I realize how important it is but get confused with all the languages, opinions, and complications involved in setting up an IDE etc.

    • Vinicius Vacanti

      I would follow this:

  • Miguel

    thanks for the advice and good timing! 🙂

    • Vinicius Vacanti

      Glad you liked it!

  • SeedStager

    Great post Vini! I wonder, if you would recommend to go with Py/D or RoR for beginners and why?

    • Vinicius Vacanti

      It doesn’t really matter in the end. If you have a friend that knows either, go with that.

  • Chris Kong

    We are building a B2B product. I would also add…getting feedback and some validation from all the business customers are important.  Getting them super early even during product development stage. There is so much you can learn about your idea/product based on their initial thoughts and all the problems their businesses are facing.

    • Vinicius Vacanti

      Definitely. Should have had that on my list!

  • Tray

    Refreshing to hear an honest talk with yourself from 5 years ago.  A couple of points hit home with me.  Instead of thinking about a conversation from 2007 what if today was the day you came back from 5 years in the future, from 2015? What would you say to yourself today?  I pose this question not to try and predict which language would be best or other unknown variables but more of a mindset. 

    For me it is the way of looking at situations that needs to be changed.  Once I get better at this, the variables will not matter so much.  I will have a better chance to do the right thing regardless of what set of options are possible at that point in time.

    A way to future proof myself?

    • Tray

       Maybe one of things I would say to myself is proof your writing better.

      Make that 2017 🙂

      • Vinicius Vacanti


  • Dluquetta

    Why do you say python/django or ruby on rails versus other languages?

  • Jonathan Chambers

    Awesome Post it reminds me a lil bit of myself right now..LOL Thanks a lot for the advice.. Let me know if there’s any way I can help you…

  • Huasongchang808

    very  good!

  • Tyqoo

    Hi, I’m a college studentI love this post. aspecially the first point of view- coding. I’m not a camputer science student and never have learned about coding , but I really want to learn some. Which one of them should I learn, Python or Ruby. And how should I start.

  • Tyqoo

    Hi, I’m a college student. I love this post! Especially the first point of view-coding. I’m not a camputer science student and never have learned about coding. Which one of them should I learn, Python or Ruby. And how should I start?

    • Vinicius Vacanti

      Doesn’t really matter which you pick. If you have a friend that knows one or the other, go with what your friends knows so you can ask them questions.

  • Andrew

    Great advice, and no doubt applicable to many fields of endeavour.

  • michael beattie

    great thoughts…i liken the learning to code point to being a baseball coach…it’s going to be a lot easier to lead a successful team if you’ve got a background in the game…

  • Steven

    Why don’t you suggest learning PHP over Python/Rails?