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Why I Didn't Start Instacart

Instacart recently announced a $271 Million funding round, and Sergei is reminded about a very similar concept he wanted to start around the same time that Apoorva Mehta started Instacart in 2012. The only difference was that Apoorva had a way to execute immediately, and Sergei did not. That's why the idea didn't matter, in that case, as much as the immediate ability to put something into market, and see if it's viable. And that's exactly what Apoorva did. Listen to this edition of the 5...


Teespring's Meteoric Rise And What Happened After They Raised $65 Million, with Evan Stites-Clayton

How do you know if it's the right move to give up on a business you've been working on for over half a year? When Evan Stites-Clayton was approached by his co-founder Walker to give up on their business, a job site for college students, to work on a completely new product, a t-shirt company, he had to make this difficult decision. While throwing away months of hard work was painful, the new project was difficult to ignore. It had generated thousands of dollars after just one weekend of work,...


5 Minute Pick Me Up - The Shark Tank Episode That Almost Never Aired

The company I had been advising was just served a cease and desist order from a major brand to change their name, and it was about to put at risk their chance of having the Shark Tank episode air that would likely make the difference between success and failure for their fledgeling startup. It was the Friday night before the Monday deadline by which the startup had to have this issue resolved, that in a last ditch effort I decided to cold email an executive in the brand that held the...


Becoming A Top 100 Comedy Podcaster With Jared Freid

Performing alongside Jim Gaffigan and Dennis Leary at The Boston Garden would be a massive accomplishment for any comedian. For Jared Freid, it felt like a bar mitzvah. It was clearly a new milestone in his life, but it was also just one night - a fleeting moment that would mean nothing without continued focus and dedication to his craft. Since leaving his job in insurance to pursue comedy full time Jared has treated his career like a business, constantly putting out new content while...


5 Minute Pick Me Up - How You Can Build Entrepreneurial Skills Through Community Work

The upcoming election on Tuesday inspired us to talk about our first ever entrepreneurial pursuit in High School that ended up teaching us many lessons that we still use when starting businesses. As sophomores, we found out about a political debate club, Junior Statesmen of America, that taught kids how to debate real issues in congress style debates, and decided to bring it to our school. The only problem was that our principal decided not to sanction the club. That meant that we had to...


Growing An Alcohol Delivery Marketplace To 40 Cities With Lindsey Andrews Of Minibar Delivery

As a first time entrepreneur it's easy to doubt yourself, or come up with excuses for why something will not work. Maybe you don't know the industry well enough, or you can't find a technical co-founder, or you've never done sales. When starting Minibar, Lindsey Andrews and Lara Crystal didn't have experience in any of these areas, but they saw a massive opportunity and simply focused on execution instead of letting doubt consume them. Four years later they're in 40 states, servicing 90% of...


5 Minute Pick Me Up – How To Make Decisions Like A Fortune 500 CEO

Busy leaders have to make dozens of important decisions on a daily basis. While everyone’s process is slightly different, there are some common practices that almost every successful CEO and leader follows. In this episode we talk about: 1) Removing unimportant decisions from your day 2) Practicing being uncomfortable 3) Why meditation can help you avoid acting on impulse …including stories from successful comedian Bill Hader and former President Obama.


The Three Books That Will Change Your Life

It's not often that a book can change the way you approach your day to day life or impact some of the most important decisions you make. Once in a while you come across something so timely that it feels like it was written just for you - just for this exact moment in your life. In this episode we discuss three incredible books that shaped our outlook on life and the way we approach our businesses and careers. We start with Dale Carnegie's How To Win Friends and Influence People, which taught...


5 Minute Pick Me Up - The $30,000 Side Hustle

This week we met an entrepreneur who told us about a side project he did that ended up making him and his partner $30,000 in just 2 months. The story is about how one young entrepreneur started an exotic car meet up in his home town that ended up growing to a sizable community, and how he eventually found a business opportunity in shooting high quality car videos for businesses.


Becoming A Venture Capitalist With Diego Berrio

How do you become a venture capitalist with no previous VC experience? Our guest this week, Diego Berrio, was able to create a venture career for himself with no previous track record as an investor. When he realized he wanted to leave the world of traditional finance to become an investor after years of running finance at an education software company, he did what any savvy entrepreneur would do and created the opportunity for himself. In this episode we dive into Diego's early career, and...


5 Minute Pick Me Up - The Making of Jackie Chan

Jackie Chan is well known for breaking every single bone in his body throughout his successful career as a martial arts actor, but in this episode we talk about the little known story of the rigorous upbringing that turned him into the most daring stuntmen in the business. If you're facing difficulties in your life, your ability to be disciplined enough to push through is what will ultimately bring success your way. Jackie's entire career was fraught with ups and downs but he always kept...


From Trading Stocks To Building A Pet Care Startup, With Throw Me A Bone

Getting Sting and the CEO of Goldman Sachs to trust your business with their dogs is a pretty positive indicator. When the Great Recession hit in 2008, Mike Lavora and Adam Light were working on Wall Street. Within 12 months after being forced to leave their jobs, they were doing six figures in revenue with their new dog walking business. What started as a simple services company has now grown to 45 employees, and 7 locations across New York City. Turns out the market for pet care services...


5 Minute Pick Me Up - The Email That Got Us The Meeting

This episode is a follow up to Episode 39 - Starting a Revenue Generating Training Business in 3 Weeks. Here we read you the exact email we used to get 10 meetings with coding bootcamps, to ultimately close our first contract just weeks later.


The Reality of Fundraising and How Most Entrepreneurs Get Capital

Most founders will never raise a single dime from investors. This has nothing to do with your capabilities as an entrepreneur. It's simply the reality of venture economics and the fact that most businesses don't fit the requirements of a professional investor. The good news is that 95% of business are able to find capital through other means. In this episode we describe how most entrepreneurs raise capital through four main channels - credit card loans, bank loans, money from friends and...


5 Minute Pick Me Up - Creating Your Own Daily Routines

There is no one size fits all solution that makes everyone productive. To accomplish your goals, you have to find what works for you, and create your own set of daily routines and rituals. The key is consistency. This episode was inspired by the book "Daily Rituals" by Mason Currey, and an article by Pia Silva entitled "9-5 Is Out. Try The 1-6 Instead." In this episode you will hear: 1. How George Orwell changed his life at 31 to be able to work on his writing and support himself. 2. What...


The Importance Of Saying Fu*k It

Woody Allen famously said that eighty percent of success is showing up. Often times the most effective way to consistently get yourself to show up is to simply say “fu*k it”. This means putting insecurities and doubts aside. It means ignoring the voice inside your head that incessantly tells you why something might not work out. It means removing all expectations and letting things simply play out. In this episode we talk about how we were able to get fast and incredibly impactful results...


5 Minute Pick Me Up - Update to Testing A New Idea Episode

This is an update to episode 41, the recent episode about a new idea that we decided to test.


Turning a Gelato Shop Into a 16 Store Franchise, With Frost Gelato

Is it possible to build a successful business with your best friend? Stephen and Jeffrey of the Frost Gelato Shoppe franchise seem to think so. They’ve been friends since second grade and credit the deep trust that they’ve built up over their entire lives to helping them survive over 13 years of being in business together. But how do you go from never starting a business, to opening a Gelato shop in an underdeveloped part of Tucson Arizona and franchising the business within just three...


5 Minute Pick Me Up - The Case For Doing Door To Door Sales

Often, as a founder, you have to be willing to do things that others aren't. In this 5 Minute Pick me Up episode we talk about why seemingly antiquated techniques like selling door to door, are a great way to get business in the early days. We also tell the story of 2 founders that we worked with who came up with an idea for a product that would be great for restaurants, and validated that it had a huge potential market by talking to 80 restaurant owners in 3 weeks.


How Kyle Bergman Sold 6 Figures In Sweatpant Overalls While Working Full Time And Going To School

Most apparel startups don’t generate 6 figures in gross profit within 1 year of launching. But then, most apparel companies aren’t run by a solo entrepreneur who until recently was balancing working on his business with a full time job at Birchbox, pursuing his MBA at NYU, working part-time as a physical trainer at Orange Theory, and playing for the Israeli National LaCrosse team. If that wasn’t enough, he’s also a photographer and videographer on the side and occasionally works with major...