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Best of Bootstrapping: English Major Bootstraps a Tech Company

Posted on Friday, Jan 10th 2020

Kevin Groome, Founder of Pica9, has done an excellent job of bootstrapping his tech company without a tech background. Inspiring story for many in his shoes.

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?

Kevin Groome: I grew up in Princeton, New Jersey. I went to school there. I had the good fortune, in those early years, to be around a bunch of people who weren’t famous at that time but went on to be very famous. I went to History class with Jeff Bezos. I went to English Literature class with Michelle Obama, and I even went to acting class with Brooke Shields.

Sramana Mitra: Are you in touch with any of them?

Kevin Groome: No, unfortunately for me. However, one thing that I noticed about all those folks, who didn’t just grow a small or mid-sized business, is how much they care about individuals. How they devote time to individuals? You see that. This is true across leaders in advertising, manufacturing, and healthcare. I found them very approachable.

Sramana Mitra: Let’s come back to your story. What happens after you get out of Princeton? What did you study in Princeton?

Kevin Groome: I studied English Literature and Theater. I was as far away from technology as you could possibly get.

Sramana Mitra: I actually love both literature and theater. I am a computer scientist by training, but I have a deep affinity for literature and theater.

Kevin Groome: If I had a skill that I could offer to employers when I was young, it would probably be that I could string words together pretty well. I moved as far away from the East Coast as I could get without leaving America.

I ended up in San Francisco back in the mid 1980’s as a writer. The technology companies were in desperate need of writers to try and simplify complex stories and to tell those stories in a way that was consumable.

About three months after I graduated, I got my first writing assignment from a software company. That’s where my first business took off. It was all happenstance by applying the skill I identified I have to the needs of a community of customers who didn’t really have a lot of writers. Technology seems a little bit nerdy. Maybe it wasn’t quite fashionable. You wouldn’t see the great creatives in technology at that time. You would find, instead, a lot of opportunity. That’s where I grew my business within the first five or six years of my career.

We ended up creating a marketing communications practice that just specialized in high technology and had a blue-chip client list by the time we rolled around in 1991.

At that point, I got married. I got married to about a classic humanities person. That adventure took me back to New York. That’s where I merged my company with an advertising agency. We created one of the high tech specialists in the New York community.

Sramana Mitra: What year does this bring us up to?

Kevin Groome: That gets us up to 1993. The agency is now working only with high technology clients. We became known as W&G Advertising. We grew that marketing communications and advertising practice. By about 1997, we were in the top 20 high-tech advertising agencies in the US.

We picked a niche, and we stuck to it. New York, of course, is a wonderful place to get advertising clients. We decided to forego the general and focus on high tech. It worked quite well. We did get known for getting what software and hardware companies are trying to say, and who they’re trying to say it to.

Some of our clients included a wonderful organization called Cheyenne Software. They became a part of Computer Associates. The mergers and acquisitions pulled us up the funnel. By 1997, we were one of the top 20 in our category. It was an exciting ride.

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
. Onit CEO Bootstraps First, Raises Money Later
. Pura Vida Founders Bootstrap to $130M
. Lawline CEO Bootstraps to $10M
. Bootstrapping a Technology Product Company from India
. Codesigned CEO Bootstraps Using Services
. Rukkus CEO Follows Bootstrap First, Raise Money Later Strategy
. Bootstrapping and Managing a Successful Pivot
. Ukrainian Entrepreneur Bootstraps to Global Scale
. Bootstrapping a Niche E-Commerce Venture
. Bootstrapping Planon to $100M from The Netherlands
. Co-founder Bootstrapped with a Paycheck from Indiana
. Bootstrapping an Education Company
. Bootstrapping an IoT Company from North Carolina
. Serial Bootstrapper Bootstraps to $27M
. Bootstrapping Identity Automation Using Services from Houston
. Bootstrapping ProjectManager.com from NZ, Scaling in the US
. Bootstrapping to $15M in Three Years
. Peruvian Entrepreneur Bootstraps to $200M
. JotForm Founder Bootstrapped with a Paycheck
. WeGoLook was Bootstrapped from Oklahoma
. Bootstrapping AutoClaims Direct to $15M
. Meltwater Founder Bootstrapped to $200M
. Bootstrapping to $20M From London
. Synechron CEO Bootstrapped to $300M
. Unique Vintage was Bootstrapped with a Paycheck
. Toptal CEO Bootstraps a Virtual Company to Scale
. Bootstrapping to $45M from Chicago
. Vacasa Co-founder Bootstrapped to $100M
. Bootstrapping Infinitely Virtual All The Way
. Bootstrapping to Exit Discussion with David Lambert, Right Side Capital Management
. Bootstrapping a Healthcare IT Company to $100M
. Discussing Seed Rounds with Cindy Padnos, Illuminate Ventures
. Auction.com Bootstrapped to $180M in Online Real Estate
. Discussing the Silicon Valley – India Corridor with Naren Gupta of Nexus Venture Partners
. Bootstrapped with a Paycheck to Techstars and Acquisition
. Discussing People vs. Market with Jon Staenberg, Staenberg Venture Partners
. Bootstrapping a Highly Profitable Company in Social Media Marketing
. Discussing Investments in Indian Startups with Anand Daniel, Accel Partners
. Bootstrapping an Evergreen Business from Oregon
. Discussing Startups in Africa with Osayi Igharo, Ripple VC
. Investing in Concept Stage Startups with Matt Holleran, Cloud Apps Capital Partners
. Serial Entrepreneur Bootstrapped Two Startups to Huge Revenue
. Discussing Investment Strategy With Deepak Jeevankumar, Dell Technologies Capital
. Bootstrapping Hotelplanner.com to $20M with Intelligent Financial Engineering
. Discussing Investing Across Sectors in India with Swapna Gupta, Qualcomm Ventures
. Bootstrapping Cleverbridge From Germany
. Discussing Open Opportunities with Hemant Mohapatra, Lightspeed Venture Partners
. Bootstrapping E-commerce Company Fun.com
. Discussing Seed Rounds with Bruce Cleveland, Wildcat Venture Partners
. From Friends and Family Funding to $30M Exit
. Discussing the Evolution of the Indian Startup Industry with Sasha Mirchandani, Kae Capital
. Lean Company Bootstraps to $7M
. Saatva Co-founder Bootstrapped a $25M E-Commerce Company
. Looking at Terms with Heidi Roizen of Threshold Ventures
. ADDA Co-founder CEO Bootstrapped with a Paycheck in India
. Duda Co-founders Bootstrap with Paychecks
. The Importance of Building Value with Shomit Ghose, Onset Ventures
. Get Real Health Founder Bootstrapped Using Services
. Bootstrapping Unique Vintage Using a Paycheck
. Discussing E-commerce Startup Trends with Daniel Gulati, Forecast Fund
. Bootstrapping a Digital Startup with a Paycheck
. Discussing Seed Stages with Amir Banifatemi of K5 Ventures
. Bootstrapping Avelead Using Services from Atlanta
. Founder Bootstrapped a Big Data Company Using Services
. Discussing Future Unicorns with Warren Weiss, Foundation Capital
. Founder Bootstrapped Axosoft with a Paycheck
. Raised a Series A with $10 Million in the Bank
. Discussing Unicorn Investments with Ravi Mohan of Shasta Ventures
. Bootstrapping a $7M Company in Houston
. A View into Pre-Seed Funding with Gaurav Jain, Afore Capital
. Bootstrapping to $13M in Niche E-commerce
. Discussing European Startup Funding with Alastair Mitchell, EQT Ventures
. Founder Bootstrapped Category Leading E-commerce Company Shoplet
. Discussing Trends With Yanev Suissa, SineWave Ventures
. Founder Mark Organ Bootstrapped Eloqua and Crowdfunded Influitive
. Sourcing Global Ventures with Ann Winblad of Hummer Winblad
. JAM CEO Survives Covid with a Bootstrapped Venture
. E-commerce and Investing with Tod Francis, Shasta Ventures
. How An Entrepreneur Couple Bootstrapped RuffleButts To $5M
. TextMe Founders Bootstrapped an App to $10M
. Bootstrapped Journey of a Child Entrepreneur in India
. Discussing Alternatives to Traditional Venture Capital with Bryce Roberts, Indie.vc
. Solo Founder Bootstrapped Wingify to $7 Million in India
. Co-founder Bootstrapped a SaaS Company in India
. Bootstrapped MindTouch to $12M+ and Exit
. Mobiliya Technologies was Bootstrapped Using Services
. What Traditional VCs are Looking for with Scott Sandell, NEA
. Bootstrapped Srishti Software Applications with Services from India
. How Robust SaaS Company RateGain was Bootstrapped from India

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