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.

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).

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.

  • http://www.frankdenbow.com Frank Denbow

    Great to hear things have come full circle after these years of working towards it. Congrats! I am just getting started again on this path and appreciate all that you share with us about your journey.

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks Frank!

      • Irrakio

        Please tell your experiences, teaches a lot. Ever been told, you’re crazy as you leave your job, your security and future. Ever felt that his ideas were completely opposite to most people. That was to deal with these personal questions.

  • http://twitter.com/schuylercbrown Schuyler Brown

    You got balls kid. Failure sucks, uncertainty is nerve wracking, but the pride you get from fighting like hell to achieve your dream is something money just can’t buy. Life in the startup trenches is not for everyone, but for everyone who is in it, trying like hell to build something and make that stage, you’re a true inspiration. Congrats.

    Schuyler

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks Schuyler.

  • Jacobespa

    In the trenches now and needed to hear this one. Thank You.

    • http://viniciusvacanti.com Vinicius Vacanti

      Single-handedly makes writings this post worth it. Good luck.

  • http://twitter.com/ejengstrom ejengstrom

    Congratulations on completing your four year education. Good luck to you and Yipit.

    • http://viniciusvacanti.com Vinicius Vacanti

      Definitely felt like an education.

  • http://christainnewyork.com Christa Avampato

    What an inspiring and honest story! Bravo to you for having the guts to start Yipit and to write about it so clearly. Thank you!

    • http://viniciusvacanti.com Vinicius Vacanti

      Just hoping to motivate others and support those in the process.

  • http://www.facebook.com/desikid Vipul Sharma

    I dont think there could be anything more inspiring than this!!

    • http://viniciusvacanti.com Vinicius Vacanti

      Ha. There definitely are but I’m glad you enjoyed it.

  • http://twitter.com/JGailor Jeremy

    One interesting thing about your situation that I think definitely gave you a leg up, having gone through the process of building my own company, is that you seem to have built a large amount of cash reserves from your finance position that you could use to give yourself the freedom to think only about Yipit.

    How much of an impact do you think that had on your ability to fail, learn, and interate repeatedly until you got it right?

  • http://twitter.com/JGailor Jeremy

    One interesting thing about your situation that I think definitely gave you a leg up, having gone through the process of building my own company, is that you seem to have built a large amount of cash reserves from your finance position that you could use to give yourself the freedom to think only about Yipit.

    How much of an impact do you think that had on your ability to fail, learn, and interate repeatedly until you got it right?

    • http://viniciusvacanti.com Vinicius Vacanti

      That was huge. Definitely built up some savings but I could have also learned a lot faster than I did.

  • http://seoagencies.com seo agencies

    The thing to remember with entrepreneurship is that it’s never an overnight success. For every overnight success you read about in the media, you can look back and see the 3-4 years of grinding thankless work, that went into getting there.

    The key is to keep trying and failing, because sooner or later, you’ll get that perfect combination that’ll make all those early years worth it.

  • http://seoagencies.com seo agencies

    The thing to remember with entrepreneurship is that it’s never an overnight success. For every overnight success you read about in the media, you can look back and see the 3-4 years of grinding thankless work, that went into getting there.

    The key is to keep trying and failing, because sooner or later, you’ll get that perfect combination that’ll make all those early years worth it.

    • http://viniciusvacanti.com Vinicius Vacanti

      Great point. Rarely is a startup an overnight success.

  • Jijoy

    Thanks for sharing this  . Inspiring , it is . 

    • http://viniciusvacanti.com Vinicius Vacanti

      You, I thank.

  • http://www.tanayj.com Tanay

    Great story. Sort of related question: Do you think the couple of years in finance helped you in terms of making you better prepared to succeed in the start up world, or would you recommend one starts something right out of college?

    • http://viniciusvacanti.com Vinicius Vacanti

      If you don’t feel your ready, I would recommend working at a startup and doing things on the side. Teach yourself to code, learn about user interfaces, lean startups. Go to hackathons.

  • Anonymous

    vin, you rock. this is so inspirational

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks Lexi!

  • http://about.me/andrewoved Andrew Oved

    This is awesome. I have a similar question to Tanay- do you wish you had tried to start something earlier, or was the finance experience a crucial part of the path to your success?

    • http://viniciusvacanti.com Vinicius Vacanti

      Wish I had started earlier. Finance experience was good but not tall that relevant. It did give the funds to keep supporting myself while I struggled.

      • http://about.me/andrewoved Andrew Oved

        Good to know- thanks! Rooting for you and the yipit team

  • http://www.facebook.com/hsparikh Harshil Parikh

    Almost to the day two years ago, I remember exchanging emails with you and Jim regarding my Yipit signup link – it didn’t work! I have been following Yipit’s progress loosely since then, and its truly inspiring to see how far you guys have come. 

    Funnily enough, I too quit my job in finance and moved from NYC to Mumbai ten months ago to build something of value, and here I am learning Django, html, css, and javascript to build an MVP of my site (no tech cofounder ftw!).

    Its stories like these that keep me going when doubts start to creep in from time to time about what I am trying to build and if it will ever see the day of light. 

    Thanks for writing!    

    • http://viniciusvacanti.com Vinicius Vacanti

      Love the idea of going to another country to start a company. Kind of wish I had gone back to Brazil.

  • http://technbiz.blogspot.com paramendra

    Congrats on getting featured on TechMeme. That is where I found this blog post. 

    • http://viniciusvacanti.com Vinicius Vacanti

      Ha! Yes. Never thought I would get on techmeme.

  • http://twitter.com/dennyferra Denny Ferrassoli

    I’m also a Brazilian immigrant (well I was a year old when we moved here) and working in the startup space. Great to hear your story, please continue to share more!

    • http://viniciusvacanti.com Vinicius Vacanti

      Lots of Brazilians immigrants out there. One of the instagram founders is Brazilian.

  • nigel

    What a fantastic article! I really enjoyed it. You made my day.

  • http://www.facebook.com/kennygrant Kenny Grant

    awesome, thank you

  • http://giffconstable.com giffc

    Vin, this is one of my favorite posts of yours. And I can sure relate (although private equity pays a lot more than M&A). Startup life has given me plenty of scars but there is nothing like it and I’m rooting for Yipit 1000%.

  • http://www.thesharedweb.com Kareem Amin

    Very insightful post, thanks for sharing this, very motivating.

  • ChrisG

    Thanks for this post Vinicius. I’m an aspiring entrepreneur/kid from Seattle and found this post so moving. I feel like I share many of the same qualities/beliefs as you, and really enjoyed hearing about your success(and failure!) on your journey. If/when I get off stage one day, i’m going to reach out to you and reference this post as my inspiration. Best of luck!

    • http://viniciusvacanti.com Vinicius Vacanti

      Awesome. Best of luck!

  • Anonymous

    Wow… very similar to my experiences very recently… I am currently in a stage where I have been seeing people achieve things which I know I can achieve… but somehow I am not having the balls to leave my well paid job to start up…. As you pointed out… Only time will test my limits…. 

  • http://twitter.com/TailgaterApp Tailgater

    Really enjoyed this.  More ammo, check.

  • Anonymous

    Awesome, Inspiring Story. 

  • http://technbiz.blogspot.com paramendra

    What motivates people? Not money. Recognition does. 

  • LJ

    Hey Vin, great post!  Do you have any advice for fellow business folks (who have no tech experience/knowledge) who want to get in the social/digital/tech game?

    • http://about.me/andrewoved Andrew Oved

      Read a LOT. Read Vin’s entire blog, as well as Fred Wilson’s, Chris Dixon’s, Mark Suster’s and Eric Friedman’s for starters. (if you don’t have time to read their entire blogs, at least revisit each of their last 20-30 posts). There are a ton of more resources out there, but those are my favorite.

      Also, this may not be applicable to you depending on where you are, but I recommend going to some tech events. If you’re in NY, this is very easy. There are multiple events a day. But if you’re somewhere without a tech scene, it may be tough. Either way, reading is always available so that’s my #1 recommendation.

      • http://twitter.com/DC_Alm DC Alm

        Great Andrew. Reading is the most precious asset that a founder have when he/she is alone or outside of a tech-scene. I suffer this problem but, as you said, Read a LOT!

        Thanks

  • Anonymous

    Brilliant and inspiring article for those of us starting on that path

  • Niraj Shah

    Great post.  I was in a similar situation where I left my cushy high finance job to do what I really loved… create something.  It’s amazing to see your vision working and solving a problem… small or big.

  • Yong Park

    I just started doing strategy for TwoSides.co. 

    I really needed something to inspire me and keep my doubts in check. Thanks a bunch. 

  • http://twitter.com/WebThinker Jig Shah

    Great.

  • http://www.lawschoolrequirements.info Sam Timmins

    I walk into work each day with that same thought process about leaving a mark. Not sure I have the guts to make the jump but this definitely provides the motivation to keep plugging away in my spare time. Thanks for sharing.

  • http://pulse.yahoo.com/_KVENBUWVJS34A75QIFRGGXJGLA Blake

    Beleza, cara! Makes me want to give a digital high five to everyone in the room. 

  • Harsha

    It would be so unwise to just read such an amazing post and leave with out actually congratulating. Congratulations for whatever you are now! Just makes me realize that money is not the motivation for success, recognition is the key! 

  • JoeHobot

    Great story, almost similar to what I have been through (from Bosnian war), except that I was two times clinically dead? :)

    Keep’it going…you did great…

  • Take-A-Chance

    Fantastic story.
    While my situation is not about starting a start-up, but joining one, I had similar feelings throughout the process. Out of college, got a secure job in a cubicle with at&t. Was there for nearly 6 years before the glamour of young start-ups became attractive enough for me to loosen my grip on my safe corporate job and just jump into a company of less than 20 people; with a pay-cut! This was back in 2007. Today, everything is going better than I hoped and I’m glad I took the leap of faith. Anyone out there, if you really feel the desire deep inside, don’t ignore it. No matter what failures may lie ahead, it will never be worse than the feeling of regret 10 years down the line – when you say to yourself “What if I had did that thing back then….”.

  • http://www.clipik.com Pablo Lema

    This is a great post and glad to hear someone with some gravitas mentioning it.  Many of us who went into finance realized, maybe a bit too late in life, that we wanted to do something else, something more ground up.  Too many people in the valley plaster the label of finance/consulting on people and assume they could never be an entrepreneur. That type of generalization is childish.  I wish I had chosen to get a CS degree a while back but I didn’t, I don’t regret it, and now I’m “in the trenches” as Jacobespa said. 

    Valeu Vinicius!
    Pablo

    • -A

      Hey Pablo, my situation kind of resonated very well with yours. I didnt have a CS degree in my Engineering but invested much of my personal time in learning programming. I was held in high regard as a programmer even by the CS class-maters. Then I got job a programmer with a wonderful start-up and then with one of the top product companies. I love technology a lot. But somehow got herded into going to B-school (the top-most in my country) after 3 years in technology industry. Since I got admit to #1 B-School, I was pressured even from peers to take it up though my mind was struggling between choosing a technology vs MBA career. By some stroke of luck, I ended up into a PE firm after B-School. More golden handcuffs. :)

  • http://www.facebook.com/profile.php?id=1104051 Michael Zhang

    Vin – great point on how many years it took to get to where you are today. Nowadays, entrepreneurship is the hot thing to do, but it’s also inflated expectations and shortened timelines. Too many guys expect to just have an idea and close a round in a month – otherwise they get frustrated and fall into despair when there’s no traction and they can’t quite learn to code. Sometimes it take a while, and this is an awesome example of how perseverance is incredibly valuable.

    Here’s one question I have for you: if you were in the shoes of someone making $50k instead of $250k, how would you have approached it? From the looks of it your frugal nature and your high salary gave you the freedom to provide living expenses for several years. Many guys I know don’t have that luxury at such a young age.

    • http://twitter.com/danelbert Dan Elbert

      Seconded – would love to get your thoughts on this, Vin. Either way great post.

      • Anonymous

        Thirded. 
        Call me cynical, but it doesn’t seem like much of a trial to succeed in any endeavor, when you’re already sitting on a pile of cash and connections. Is the key to success risk-taking and hard work, or is it really “pick the right school at age 17, get the right connections by age 21, and earn 5 times the median salary in the US by age 25?” 
        There are a lot of people for whom failure would be more than being embarrassed in front of your peers – it would be telling your kid there’s nothing to eat tonight, again.

    • http://viniciusvacanti.com Vinicius Vacanti

      This is a great point. I was able to save a ton of the money I was making and I basically had three years of living expenses and and I almost needed all of it.

      If I hadn’t had the savings, I would have instead tried to learn by taking a job at a startup and learned as much as I could during the day. I would then go home and spend nights and weekends trying to build prototypes.

      • Ankit

        Another question Vin I would like to ask is if your work ex in any form helped you in your enterprise or to put it this way, will you recommend someone straight out of college to start and not to make some money in finance ?

  • Anonymous

    Just curious, how much savings did you have when you quit to start a company? If you’re uncomfortable giving a dollar figure (the way people usually are when the number is high) then can you just say how many months of living expenses it was?

    • http://viniciusvacanti.com Vinicius Vacanti

      I had almost three years of living expenses in New York.

  • Perttu Laurinen

    Great and inspiring story! keep up the good work!

  • http://www.migrationbox.com EduardoF

    Inspiring post, thanks!

  • http://twitter.com/rohi81 Rohit Nallapeta

    Truly inspirational. What I liked the most in the entire post is “After two and a half years of failure, we launched the third version of Yipit” and “They willed their services into existence.” and  never once did you say PIVOT (puke).

    • http://viniciusvacanti.com Vinicius Vacanti

      Yeah, too bad the word pivot has gotten away from us.

  • http://twitter.com/jimhirshfield JimHirshfield

    Way to go Vin!

  • SantiagoT

    Very inspiring post. A source of encouragement for someone who also recently left a comfortable corporate job. Thanks for sharing your story Vin. Congrats and continued success!

  • http://twitter.com/DC_Alm DC Alm

    “I knew it! I knew it!” It was my wife’s words a few hours. Yeah, she really knew that you’re a brazillian because of your “odd” name for a american standard at least.
     Wow, we had RSS subscribe your blog more than 6 months and I have never commented before in any blog or forum. But this time is different. Your history it is so similar of our story. We had a successful brazillian hedge-fund and we opted to close it 2 years ago to start a startup (my wife with a unique ecommerce model for a branded baby clothes and toys, and I with terrible idea) in Brazil. I’d personally failed two times when she had success!!! She had to learn Joomla, CSS, HTML, to create a MVP and I forced my lawyer to study together HTML, CSS and PHP. Now, I pivoted in third time and now preparing to beta test in USA and I have garnered the angel investment of 2 american investors.
     Hey “Vin”, I really believe that Yipit will capitalize that deal wave because of your unique position to got it earlier and the strong motivation that you and your partner has demonstrated.
     Congrats! And thank you very much for all your blog posts.

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks! And, yes, my name definitely gives away my Brazilian background. Good luck to you and your wife though sounds like you’re already on the right path.

  • http://twitter.com/mburgercalderon Miguel

    great job Vin!

  • Anonymous

    This was definitely inspirational and provides me with encouragement for making a similar decision I made. I hope my payoff is even fractional to yours!

    Thank Vinicius

    • http://viniciusvacanti.com Vinicius Vacanti

      best of luck!

  • Linda

    Thank you for this post! I’m a recent grad who didn’t major in CompSci but has an urge to start pushing specific-interest social networks and website designs out into the net. I’m good with HTML/CSS but I’m just getting started with Javascript, JQuery, PHP, SQL, and Python… 

    • http://viniciusvacanti.com Vinicius Vacanti

      HTML/CSS is a great place to start and then slowly move yourself down (or up) the stack to javascript, python/ruby

    • Kaitian521

      python is great

  • Anonymous

    Great story!  Congrats and inspiring

  • Alwin

    This post came very timely… love it!

  • Mike Reed

    Very inspiring… Thanks.

  • Sean

    I came from a similar immigrant background and I walked away from a great paying job to ‘make a dent’ myself.  Thanks for writing about your story.  Fair winds & following seas!

    • http://viniciusvacanti.com Vinicius Vacanti

      Best of luck to you!

  • http://twitter.com/karan6259 Karan Arora

    This is awesome! Thanks for sharing your story – truly inspirational!

  • http://twitter.com/karan6259 Karan Arora

    This is awesome! Thanks for sharing your story – truly inspirational!

  • http://twitter.com/karan6259 Karan Arora

    This is awesome! Thanks for sharing your story – truly inspirational!

  • http://twitter.com/karan6259 Karan Arora

    This is awesome! Thanks for sharing your story – truly inspirational!

  • http://twitter.com/karan6259 Karan Arora

    This is awesome! Thanks for sharing your story – truly inspirational!

  • http://twitter.com/karan6259 Karan Arora

    This is awesome! Thanks for sharing your story – truly inspirational!

  • http://www.facebook.com/vik.venkat Vikram Venkatraman

    Awesome post. Helps reassure that with the right attitude and the right moves, the light at the end of tunnel stays on. Keep crushing it!

    Vik

    • http://viniciusvacanti.com Vinicius Vacanti

      There’s always a light at the end of the tunnel.

  • http://www.facebook.com/profile.php?id=6011922 Victor Lin

    Strangely, this article is very relevant to me right now. I felt the same way you did before you quit your day job and I put in my notice last Friday. I too had been “successful” in my career, culminating with working for a major sports sunglasses company, which was my dream. But I had ideas for startups and there were people getting funded for very similar ideas. So I decided now’s the time to test myself and see how far I can go. It’s a bit scary not having the comfort of a job, but like you said “The only way to know how good you might be at something is to fail trying it.” 

    Thank you for writing this! 

    • http://viniciusvacanti.com Vinicius Vacanti

      Best of luck! Hardest step you’ve done. It’s not going to work out perfectly, just make sure you learn and keep getting back up.

      • Anonymous

        Great article Vinicius, we copy Yipit model in Singapore and doing it very well, we would like to know what is yipit’s medium/long term plans?

  • Raykoh

    Love this and experienced the same ..

  • http://www.guidingtech.com Abhijeet Mukherjee

    Vin, did you learn to code once you took the plunge? If not, I’d be really interested to know how you managed to find the right tech team and get started.

    • http://viniciusvacanti.com Vinicius Vacanti

      Tried to find a tech team and couldn’t. So taught myself. I’ve talked about that process on this blog.

  • http://twitter.com/financialsamura Financial Samurai

    Great stuff!  First of all, THANKS for showing that many of us in our mid 20s make over $200,000.  In your case, it was $250,000 at age 25.  There are so many people who think this is not possible, and they have no idea.  Making 6 figures is pretty straight forward and common place.

    Second, excellent to take a leap of faith and go for it yourself as making your own future is what it’s all about!

    Best,

    Sam
    The Yakezie

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks! And, yes, lots of jobs paying into six figures.

  • http://www.sooverdebt.com Andrea @ SoOverDebt

    Congrats on your success! This post reminds me of my favorite movie quote from Meet the Robinsons, which I use often on my site: “From failure, you learn. From success? Not so much.”

    • http://viniciusvacanti.com Vinicius Vacanti

      No shame in failing if you learn why it happened.

  • Anonymous

    Great post. Here are a couple other “why I quit my job to start a startup” stories. One is written by my friend Robert Shedd, who left a comfy consulting job at IBM to do it:

    http://blog.shedd.us/why-i-left-ibm/

    The other one I wrote, about my experience from college to full-time work on Wall Street to founding Parse.ly.

    http://www.pixelmonkey.org/2010/10/16/what-one-does

    Cheers!

    • http://viniciusvacanti.com Vinicius Vacanti

      Those are great posts. Thanks for sharing!

  • David Sandusky

    Very cool story. Congratulations on your decision. Not everyone needs to start a business to realize your great lessons, but embracing the “why” yields a great life. Fail fast, lead.  “The only way to know how good you might be at something is to fail trying it”

  • fteter

    Exactly the inspiration I needed today.  Thanks for the recharge!

  • http://www.facebook.com/sahan.pitigala Sahan Pitigala

    I’m considering quitting my “safe” government job to tackle a start-up as well, and this post validated all my reasons for wanting to do so. Congrats and thank you.

  • Chris K

    Fantastic post. This really hit the spot. Gives me a vector for how to tackle my upcoming military to civilian conversion.

  • http://www.facebook.com/amit4uall Amit Saxena

    Got my hands dirty, and haven’t achieved anything worthwhile till now…….this post provides me with enough fuel to keep going for a few more months :)

  • Kothaarianuuj

    Congratulations! Very inspirational! Keeps me going!

  • Michael Huber

    Vinny, nice post. Fascinating to read and glad you shared it. 
     

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks Michael! Hope all is well!

  • Satheesh Babu Vattekkat

    This beats any motivational speech/textbook hands down. Thank you.

  • Stelleo Tolda

    Vinicius, thanks for sharing your story – it reminded me of my own experience. I was a Brazilian working in finance in NY twelve years ago, but decided to leave it all to join a startup in São Paulo. I couldn’t be happier with my decision. Congratulations on Yipit’s success! Vai fundo, cara. Abs,

  • http://edpin.com Eduardo Pinheiro

    Great story Vinicius. Truly inspiring and motivating, and as an added bonus from a brazilian compatriot. Best of luck to you and please keep on sharing.

  • Muhammad Samir

    very motivative. Thanks a lot.

  • Pooja Bhatia

    Although ours is not a tech start-up we have faced a gazillion hurdles. We did not back ourselves financially in terms of having atleast a year’s living expenses on us, but we were lucky that our friends and family backed us. Although we are still not where we want to be, we are hoping to get there one day and this post really reinstated the belief that you need to experience failure for truly basking in your success.

  • Wanderson

    Thanks for sharing such inspirational history. Nice to see a brazilian getting things done abroad!

    PS.: Now I’m curious about Yipit! Thinking about applying for a job :)

    Congrats and good luck!

  • http://www.facebook.com/khullar.puneet Puneet Khullar

    Superb Really inspiring fact….

  • Junaid K

    This post gave me indescribable clarity. I work in PE, and been having similar self reflection experiences.  I love your honesty, thank you.

  • Francisc

    Well done, happy to hear it worked out for you. I’m in the same situation you described at the beginning of the article. Wish me luck.

  • Anonymous

    Great article Vin.  I am trying to build my own empire too.  This is attempt no. 2 for me.

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  • Tobyd

    As a CEO (out of Bain) sitting late in the office doing another VC deck for my investors this post made me feel fantastic – thank you…

    • http://viniciusvacanti.com Vinicius Vacanti

      Thanks for the nice words. Makes the post worth it.

  • http://www.johnexleyonline.com JohnExley

    Holy Motivation, Vin. This post is up there with @Arrington and @cdixon’s posts on ‘the man in the arena’. 

    Thanks for writing this man. We met (briefly) at TechStars/Pivotal Labs over the summer while I was interning for Hashable. I remember you saying that Yavo was the real deal and to focus on learning as much as I could from him. I appreciated that.

    Good luck continuing to build Yipit and congratulations on the new officespace and new digs in the LES (read about it in NYT earlier tonight)!

  • HanGu

    For those of us who are still on the fences about our own ideas and where to go, this is just what we needed. Thank you.

  • AspiringEnt

    amazing story! thanks for sharing — truly inspirational. Yipit is kick-ass and you deserve all the success you get! 

  • Null

    第一:别人只在乎你的能力和贡献,换句话说,你的着装和别人对你的期待没有多大关系;(,其实很多时候这是一种自信的体现!往往有自信的人才不在乎自己的衣着,因为他相信自己的内心和能力足够强大)
    第二:每个人在乎的只是利益(也许过激,但现实的社会不先保护好自己,结果很明显),你成功了,别人也来从中寻找利益,但重要的是确定好自己的目标,一直走下去。

    • http://viniciusvacanti.com Vinicius Vacanti

      Here’s the translation of this comment (Via google translate)
      First: people only care about your ability and contribution, in other words, yourdress and others not much is expected of you; (In fact, many times this is the embodiment of a sense of confidence is often self-confident people do not care about their ownclothing, because he believed that the heart and is strong enough)Second: Everyone cares about interests (perhaps extreme, but the social realities we do not first protect themselves, the result is obvious), you are successful, others to find the interest, but it is important to determine their owngoals, has been go on.

  • http://geexhq.com/ magesh

    Thats amazing! Thanks for sharing your experiences!

  • (^o^)/~

    ENGLISH IS SO HARD ,不懂英语的孩子真心伤不起啊

  • Chimera Swa

    I have been working for 15 yrs in software and only last year I woke up from my slumber and decided to try to build something of my own… as a fellow immigrant from India, I understand the plight of ‘save as much as we can’ mentality :D

  • http://www.facebook.com/people/Note-Suwanchote/100000266637447 Note Suwanchote

    Hello
    I was wondering how you found your team to help start your company?

  • http://www.theroadtosiliconvalley.com/ Ernest Semerda

    Thank you for sharing your story. It is an inspiration! Freeing one self from the confines of a job and walking on own feet is definitely the only way to truly learn about one self and what one is capable of. As one Persian Prophet said “It is in the darkest times of the night that you can see the stars.”.

  • http://www.grassfedpal.com/ Bill Masur

    Just found your blog.  I quit my job in March to start my own company, it’s been a heck of a learning experience.  I needed to hear this.  Loving your posts.  Thanks!!

  • http://vabulous.com/ Vania

    Love it! great story!

  • Siri

    Awesome !!! I will do the same and I already left my job .. nothing to afraid off as you said , we will learn from our success and failure , never give up … I will let you know the day that I can make my million $ , thanks for the great story …very inspiring !!!