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Best of Bootstrapping: Bootstrapping with Freemium and Free Trials to $13M

Posted on Friday, Jul 24th 2020

SurveyGizmo CEO Christian Vanek has bootstrapped SurveyGizmo to $13 million from Boulder, Colorado. He has experimented with both freemium and free trial, and has managed to monetize nicely. Read more about the strategies that have worked for him.

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?

Christian Vanek: I’m from upstate New York originally. I was born in 1977. Honestly, I moved around quite a bit. I never went to the same high school for more than a couple of years. In the end, I ended up in Massachusetts. After high school, I had no idea what to do with my life. I was not the best student ever. The beginning of my journey was probably when I decided to do a year of service for AmeriCorps as part of an urban peace corps that had started in Boston and spread around the United States. Through working in the homeless shelter there and building a software package to help manage clothing and service distribution, I got my hands dirty and started getting the bug of building software for other people.

Sramana Mitra: When was this happening?

Christian Vanek: That was 1995. I was 18. I wanted to take a gap year before college. AmeriCorps gave me a nice stipend to try college. Afterwards, I did try college, but I immediately dropped out.

Sramana Mitra: What did you do when you dropped out of college?

Christian Vanek: My mother decided to kick me out of the house if I couldn’t get a job and start making some money. Not knowing exactly what to do, I decided to temp. I found this great organization in Hanover called DCI that was doing data warehousing and computer education. I worked in their travel services group that was into conference and travel services. This was now 1997, I believe.

I worked there for about half a year before realizing that the work that they had me do was routine and I could probably write a piece of software that would do most of what I was doing. I did that. They hired me full-time at that point and gave me the latitude to build whatever software I could in order to optimize their business processes. That was the beginning of my career.

Sramana Mitra: That was your first job?

Christian Vanek: Yes, that was my first job.

Sramana Mitra: How long did you stay there?

Christian Vanek: I stayed there for about a year and a half before their parent company decided to offer me a job as a web developer on their marketing team. I actually liked that job a lot. We were working for a travel company. My responsibility was transposing credit card numbers to fax them to hotels to make reservations blocks for this conference company. It was mind numbingly tedious.

Actually, building software that would do that automatically and network from all of the travel agents together and automatically transmit it to the hotel and enter the information into the American Airline system was a lot of fun. If they had known what I was doing, I probably would have been stopped. Back then, we pretty much had the freedom to do whatever we wanted.

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
. Freightwise Bootstraps to $33 Million
. Bootstraps First to $5M ARR, Raises $10M Later
. Bootstraps in Europe, Raises Money and Goes Global in the US
. English Major Bootstraps a Tech Company
. Bootstraps with a Paycheck to $15M from Tennessee
. Queue-It Bootstraps from Denmark to the US
. Bootstrapping A Virtual Company To $25M
. ActiveCampaign CEO Bootstraps Using Services to $40M
. Alteryx Bootstrapped with Services to a Public Unicorn
. Inspyrus Bootstraps Using Services to an Awesome Business Model
. CEO Bootstraps Using Services to Millions from Russia
. Wiredrive CEO Bootstraps Using Services to $10M
. Scaling to Over $10M by Bootstrapping Using Services
. Bootstraps Using Services from Poland to a US SaaS Company
. ButcherBox CEO Bootstraps a Perishable Meat Business to Significant Scale
. Waveform CEO Bootstraps to $8M
. Bootstrapped Entrepreneurship from Estonia
. From Laid-off Engineer to Successful Startup CEO
. Imagine Easy Solutions CEO Bootstraps to Exit
. BannerBuzz CEO Bootstraps to $35M
. Bootstrapping a Virtual Company to Scale
. Bootstrapping Using Services from Wisconsin
. Best Tactic for B2B Startups
. Bootstrapping by Piggybacking from Romania
. Bootstrap First, Then Scale with VC Funds
. Bootstrap to +$10M First, Raise Money Later
. Madwire CEO Bootstrapped First, Raised Money Later to $120M
. Bootstrap Using Services First, Raise Money Later
. Wonderful Bootstrap with a Paycheck Story
. RushOrderTees CEO Bootstraps to $23M
. Bootstrapping with Freemium and Free Trials to $13M
. Bootstrapping, Pivoting, Gaining Liquidity, Scaling to $100M+
. Bootstrapping with Affiliate Marketing
. Bootstrap to Exit, Bootstrap Again, Then Raise VC Money
. Bootstrapping Using Services to $12M
. Bootstrapping an Ad Tech Company from Paris
. Bootstrapping a 100% Virtual Company from Ireland
. MiQ CEO Bootstraps with Services from London
. Bootstrapping to $8M During the Covid Crisis
. Bootstrapping a Marketplace from Brazil
. Bootstrapping Using Services from Sweden
. What Should Startups Do To Raise Seed Capital in 2021?
. EdTech Unicorn Bootstrapped First from Canada
. Coalition Technologies Co-founders Bootstrap to $10M
. Bootstrapping a Virtual Company to $10M from Atlanta
. Bootstrapping a SaaS Company with a Paycheck and Scaling
. Bootstrapping with Services to $20 Million

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