Posted on Friday, Jan 17th 2020
GreenPal CEO Gene Caballero shares a fantastic story of a founder duo bootstrapping with a paycheck, now growing from $5M to $15M in one year, with a virtual team of freelancers. Your classic 21st century internet business. No outside financing whatsoever!
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? Gene Caballero: I was born in
Lima, Peru. My dad’s side of the family are all entrepreneurs. My grandfather
had his own propeller business. We made propellers for boats. My dad
actually has that business now. I’m the black sheep. I’ve gone into the
technology side as opposed to the manufacturing of propellers.
raised in Nashville, Tennessee and went to college in Middle Tennessee State
University. I also got my Master’s at MTSU. I started in the corporate world. I
was in technology sales for 10 years until the opportunity for GreenPal came.
Up until then, I was looking for a way to do my own thing. Some friends were
chatting about different ways to make money and the pain points.
lot of young entrepreneurial kids who mowed lawns for a living at some point in
their life. We knew that there was a possible business in that industry. It’s
been pen and paper. It has been a cash business. When we first started in 2012,
that was the time when Lyft and Airbnb were gaining traction on the West Coast.
If people were going to summon a stranger to come and pick them up and drop
them off, at some point they would sign on lawn care. That’s the reason we
Sramana Mitra: When
did you start GreenPal? Gene Caballero: We officially
launched it in April of 2012. Sramana Mitra: What
was going on around you at that time? Gene Caballero: I was just
immersed in my day-to-day corporate life. One of my childhood friends who had
started a landscaping company grew that to be one of the largest in the area.
He was talking about pain points that he had with his business. He wanted to
grow faster but couldn’t. It was all word of mouth or traditional advertising.
He explained the pain points of all that to me.
I had heard
of Airbnb and Uber just because I was in the tech side of things. I was privy
to new startups that are hot because my territory was on the West Coast. We put
our heads together and knew that there had to be a better way for a homeowner
to find a landscaping professional and also for a better platform to ensure
that landscaping professionals can run their business more efficiently. After a
few weeks of conversation, that’s when we decided to go for it and put it all
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 More »» . 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 . 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Bootstrapping Using Services and Scaling Using Content Marketing . Bootstrapped from London, Went Public and Scaled to $450M . Bootstrapped Credit Card Processing Business Payscape . Bootstrapped TEOCO to $175M with Services . InRule Was Bootstrapped Using Services . HighQ was Bootstrapped Using Services from London . Ingenious Med was Bootstrapped with a Paycheck from Atlanta . Bootstrapped VistaVu to $10M from Canada . OnSIP CEO Mike Oeth Bootstrapped in Pennsylvania . Pramata Founder Bootstrapped in Minnesota . Conversocial was Bootstrapped Using Services from London . Zephyr Health Bootstrapped First, Raised Money Later . iText was Bootstrapped from Belgium . CTO Bootstrapped InteliSecure Using Services from Colorado . Bootstrapping Evariant Using Services . Dave Elkington Bootstrapped Billion Dollar Unicorn InsideSales.com Using Services from Utah . PMG Founders Bootstrapped Using Services from Atlanta . Ensighten Founder Bootstrapped First, Raised Money Later . 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Bay Dynamics Co-founders Bootstrapped Using Services . Building an AI Software Company from Dallas . RJMetrics Co-founders Bootstrapped First, Raised $22M Later . Bootstrapping Niche E-Commerce Business BuyAutoParts to Exit . TemplateMonster was Bootstrapped to $15 Million . Bootstrapping Edge Hosting to $18 Million . Bootstrapping, Fund Raising and Exiting with Sefaira . Bootstrapping IdeaScale to $5M from Scratch . Bootstrapping to $10M from Finland . Happy Grasshopper CEO Dan Stewart Bootstrapped to Inflection . Bootstrapping Gravity Pro Using Services . Founder Builds Multiple Bootstrapped Education Software Companies . Bootstrapping to $10M from Australia, Raising $25M from the US . Bootstrapped Y Soft to $30M from the Czech Republic . Bootstrapped from Belarus, Raised Money from Silicon Valley . Bootstrapped SproutLoud to $30M from Florida . Bootstrapped 2600Hz Using Services . A Serial Bootstrapping Entrepreneur’s Journey . Bootstrapped First, Raised Money Later from Udupi, Karnataka . Bootstrapped with Services, Raised Money, and then Acquired by Salesforce . Bootstrapping Niche E-Commerce Company Modded Euros . Bootstrapping KURU Footwear from Utah . Bootstrapped to $5M First, Raised Money Later . Ninth Wave Founder Bootstrapped Using Services . Bootstrapping Vantage Circle from Guwahati, India . Bootstrapping JobNimbus First, Raising Money Later . Bootstrapping Infragistics for 30 Years . Bootstrapping Zimit Using Services to $10M . Entrepreneur Couple Bootstraps an E-commerce Business Using a Paycheck and Crowdfunding . Co-founders Bootstrapped Using Services, then Raised $10M and Scaled to $16M . SearchStax Founder Bootstraps to $10M Using Services . Bootstrapping an AI Startup Using Services . Bootstrap to Exit and THEN do a VC-Funded Venture . Bootstrapping Using Services to $26M and a Fabulous Exit . Solo Entrepreneur Bootstraps with a Paycheck to over $15M . Bootstrapped and Later Raised Money from Oregon . Bootstrapping Evenica by Piggybacking . Bootstrapping a Vertical CRM Product using Services . Bootstrapping Using Services from Helsinki, Finland . Solo Entrepreneur Bootstraps First, Raises Money Later in Utah . Art.com Co-founder on Bootstrapping First, Raising $30M Later . Bootstrapping to Exit . Why is Bootstrapping So Important? . How Can You Play the Low-Probability Game of Start-up Funding Intelligently? . Don’t Go to VCs as Beggars – Go as Kings! . Excess is NOT a Requirement for Success . Bootstrap First, Raise Money Later . More Bootstrapping to Exit Case Studies . The Buy Side of Bootstrap to Exit Startups . Blitzscaling versus Bootstrapping . Bootstrapped Unicorns . Bootstrapped from Arizona to $10M . Bootstrapping Under30Experiences to $5M . Bootstrapping Algo.ai with Services from Michigan . Seed Investors Who Like Bootstrapped Startups . Bootstrapping a Niche E-commerce Company to $20M . Bootstrap Using Services . Bootstrapping The Intern Group to $13M . Bootstrapping OnBoard from the US Midwest . Bootstrapping SmartBuyGlasses to $50M . Startup Deaths by Overfunding . Bootstrapping RainmakerForce Decisively to $5M+ . Bootstrapping a Virtual Company with a Paycheck . The Entrepreneur - VC Compensation Disbalance . Mitch Russo Bootstrapped Timeslips to Exit with Sage . Bootstrapping with Sophisticated Strategic Maneuvering . How Ownership Matters . Bootstrapping with Services from Romania to over $5M . Bootstrapping to $30M from Florida . Bootstrapping Tuft & Needle to Over $100M . Bootstrapping Linguamatics to Over $10M from the UK . Co-founders Bootstrap a SaaS Company from Finland . Entrepreneur Couple Bootstrapped to $10M from Colorado . Bootstrapping Power2Motivate to $80M from Canada . Founder Bootstrapped to Over $10M from Australia . Bootstrapping Niche E-commerce Brand Big Barker . PrecisionLender Bootstrapped to Over $10M from North Carolina . Master Bootstrappers with $1+ Billion in Exits . Bootstrapped Ultra Mobile to Over $100 Million . Bootstrapping a 2-Sided Marketplace to $10M . Bootstrapping a Virtual Company to Over $5M . Capital Efficient Entrepreneurs Turned $1M into $80M . The Journey Through Failure to Success . Bootstrapping TrendHim from a Small Town to $12M . Bootstrapped to Y Combinator and $10M Series A . Bootstrapped a Marketplace to Over $10M . Bootstrapping Freightwise to $33M . Bootstrapped First to $5M, Raised $10M Later . Bootstrapped in Europe, Raised Money and Went Global in the US . An English Major who Bootstrapped a Tech Company . Bootstrapped with Paycheck to $15M from Tennessee . Queue-It Bootstrapped from Denmark to the US . Bootstrapped a Virtual Company to $25M . Bootstrapped Using Services to $40M First . Bootstrapped Using Services to a Public Unicorn . Bootstrapped Using Services to an Awesome Business Model . Bootstrapped Wiredrive Using Services to $10M . Happily Bootstrapping with Zoho CEO Sridhar Vembu . Bootstrapped ButcherBox to Significant Scale . Bootstrapped Using Services from Poland to a US SaaS Company . Bootstrapped Waveform to $8M . From Laid-off Engineer to Successful Startup Co-founder . Bootstrapped to Over $20M and Exit . Founder Bootstrapped to Over $35M . What is the Best Bootstrapping Tactic for B-to-B Startups? . Bootstrapped a Virtual Company to Scale . Bootstrapped Using Service from Wisconsin . Bootstrapped by Piggybacking from Romania . Bootstrapped First, Then Scaled with VC Funds . Bootstrapped to $10M+ First, Raised Money Later