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Best of Bootstrapping: SproutLoud CEO Bootstraps to $30 Million from Florida

Posted on Saturday, Aug 3rd 2019

Jared Shusterman bootstrapped his company with his bar mitzvah money. Read his wonderful story!

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jared Shusterman: I was born in Miami, Florida. I’m one of the few South Florida natives. I grew up in a middle class family that had a very heavy focus on education. After I graduated high school, I went to the University of Virginia. I got a Bachelors degree with a concentration in Finance and Marketing. Shortly after that, I moved out to San Francisco and worked for an investment bank in the online media practice. That’s the quick summary of my initial upbringing.

Sramana Mitra: How long did that stint with the investment bank last?

Jared Shusterman: It was a little over a year or thereabouts. I actually started, what was then, TargetMailers. Now it’s SproutLoud. When you’re a financial analyst, you’re putting in very long hours. I had a family emergency where I wanted to get back to South Florida. That prompted me to figure out what it is that I was going to do. I had the opportunity to speak to a person who’s now a partner in the business.

He was talking about these small business marketing tools that were coming up to help small businesses with limited budget, know-how, and resources do advertising. There was an idea early on to create a product for jewelry retailers to do small business direct mail marketing. It was a very small program with 200 pieces around specific lifetime events or occasions, like a birthday or anniversary.

Shortly after leaving Thomas Weisel and trying to figure out what I wanted to do next, I had the opportunity to go out to the JCK show in Las Vegas. It’s one of the largest jewelry retailer and manufacturer conventions in the world. We created some marketing pieces and we tested the idea and validated whether jewelry retailers would buy into these programs. You’d sign up for a few months and commit to a specific amount of budget and we would just do the marketing for them.

What we learned coming out of that was, there was a real appetite and a lot of these small businesses needed help. It was then and there that I committed to coming back and starting this venture, mainly because I was 23 or 24 years old at that time. I didn’t have a family of my own. I didn’t have a mortgage. I felt like if I ever wanted to do something, now is the time to do it because my risk profile is probably the lowest it will ever be. I figured that if I’d go into it and fail, it’d be a really good education.

Our conversation continues here.

This segment is a part in the series : Best of Bootstrapping


. Bootstrapping to an Exit
. Why is Bootstrapping Important?
. How Can You Play this Low-Probability Game Intelligently?
. Do NOT Go to VCs as Beggars - Go as Kings
. Excess is NOT Required for Success
. Bootstrap First and Raise Money Later
. Some Bootstrapping to Exit Case Studies
. The Buy Side of Bootstrapping to an Exit
. Blitzscaling vs. Bootstrapping
. Bootstrapping to Unicorns
. Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million
. Mailchimp Bootstraps to $600M Revenue
. Bootstrapping from Arizona to $10 Million
. Bootstrapped Basecamp Executes a No Nonsense Strategy
. How Under30Experiences Bootstrapped to $5 Million
. Bootstrapping with a Paycheck
. How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan
. Seed Investors Who Like Bootstrapped Businesses
. How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million
. Bootstrapping with Services
. How The Intern Group CEO David Lloyd Bootstrapped to $13 Million
. How Passageways CEO Paroon Chadha Bootstrapped from Indiana
. How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million
. Death by Overfunding
. How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+
. How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck
. TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage
. The VC-Entrepreneur Compensation Disbalance
. BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering
. Tremend CEO Marius Hanganu Bootstraps from Romania
. Gesture CEO Jim Alvarez Bootstraps to $10 Million
. SproutLoud CEO Bootstraps to $30 Million from Florida
. Tuft & Needle CEO Bootstraps to Over $100 Million
. Co-founders Bootstrap Linguamatics to Over $10M from the UK
. Ownership Matters
. Vainu Co-founder Mikko Honkanen Bootstraps from Finland
. Entrepreneur Couple Bootstraps to $10M from Colorado
. Power2Motivate CEO Bootstraps to $80M from Canada
. Financial DNA CEO Bootstraps to $10M+ from Australia
. Big Barker CEO Bootstraps a Niche E-commerce Brand
. PrecisionLender CEO Bootstraps to Over $10M from North Carolina
. Master Bootstrappers with Over $1B in Exits
. Ultra Mobile Founder Bootstraps to Over $100 Million
. Bootstrapping a Two-Sided Marketplace to $10M
. Can You Bootstrap a Virtual Company to Over $5 Million?
. Capital Efficient Entrepreneurs Turn $1M into $80M
. Discussing the Journey Through Failure to Success
. From a Small Town to $12 Million
. Bootstrapping to Y Combinator and $10 Million Series A
. Bootstrapping a Marketplace to Over $10 Million

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