categories

HOT TOPICS

NEWSLETTER

If you are considering becoming a 1M/1M premium member and would like to join our mailing list to receive ongoing information, please sign up here.

Subscribe to our Feed

Best of Bootstrapping: Dave Elkington Bootstrapped Billion Dollar Unicorn InsideSales.com Using Services from Utah

Posted on Wednesday, Sep 8th 2021

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

Our tried-and-true mantra of Bootstrap First, Raise Money Later rings throughout Dave Elkington’s story. As the Founder of InsideSales.com, he used services to bootstrap a Unicorn that had raised close to $140 million in VC funding when we spoke in 2015. Revenue was scaling 100% year over year then.

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

Dave Elkington: I grew up in Utah. I went to school here. My parents are both school teachers and worked for the state and federal government. It was a little bit atypical. My dad was a rancher growing up in Idaho. My mom is from Canada. When people asked what I wanted to be when I grew up, I would tell them I wanted to be a millionaire. They would ask why. I’d be like, “Not for the money, but purely for the sake of accomplishment of being able to do that.” I went to school locally. My education is a little bit eclectic. I have an undergraduate degree in Philosophy. I also have minors in Hebrew, Japanese History, and Business. I also studied, for about a year, in Israel. I decided I wanted to go get some international experience and I had family in Israel. I dropped out of school at BYU and applied to the Hebrew University. I got accepted and transferred credits. I did that for a little over a year, dropped out of school, and applied to BYU. I got re-accepted and then finished at BYU.

Sramana Mitra: What timeframe are we talking?

Dave Elkington: This is back in 1998.

Sramana Mitra: In 1998, the Internet was already in full swing. It was, in fact, approaching a bubble. What happened when you came out with your degree?

Dave Elkington: As you’d expect, the philosophy firms weren’t hiring as much at that time frame. As pragmatic as you’d expect somebody who’s teaching high school and worked for the state government, you’d expect a little more pragmatism out of their kid. When I graduated, I had to figure out what I was going to do. I looked at consulting, banking, and tech space. I interviewed and tried to get jobs with all of them. I ended up working at Alex Brown back at Baltimore. What I was particularly interested in was observing and learning how the machine works and how people function.

Banking seemed to give me a bird’s eye view of the entire process. I’ve already done and dabbled around with some technology. Even though I don’t really have an education in technology, I already taught myself to program to some degree. It was relatively familiar, but I really wanted that bird’s eye view. Coming out with a relatively non-pragmatic degree, I sent out 200 to 300 resumes. I got about 20 or 30 interviews and got four or five offers. I was turned down 99%. I was working in their consumer group. I was involved in the Krispy Kreme IPO all the way through to Outback.com.

Sramana Mitra: How long did you do that for?

Dave Elkington: Almost two years. Anyone who’s been a banking analyst, especially at that time, understands that even though you graduate thinking you’re going to make money, you’ll probably make less money on an hourly rate than everybody else in the road because you’re working crazy hours. We joked that we were the best worst paid people in the world. The job involved running spreadsheets to making pitch books and getting coffee for the Managing Director. It was truly a thankless and tough job, but that’s where I learned a massive amount in a very small time. When I graduated, I hadn’t taken a lot of math. There were two to three weeks of Excel training. I may have opened Excel three or four times before that point. I became well-versed in PowerPoint, Excel, and the toolset that an analyst at a bank typically uses. I came in from behind where a lot of my peers had Economics and Business degrees. I was totally in over my head.

Sramana Mitra: We are now in 2000 and you have finished your tenure at Alex Brown. What happens next?

Dave Elkington: It was interesting. I watched banks and bankers make insane money for really not providing a huge amount of value into the economy. There was a value to the company, but to me, the fees felt disproportionate to the contribution. At some point, I wanted to see and help companies more. At the same time, I saw companies that were ridiculous. There was a company that was doing $750,000 and raised over $50 million. It frustrated me. I would see people who I feel were not quite as engaged and capable of making huge amounts of money and were building things that were frankly not terribly interesting.

I next chose to join a venture capital firm. I actually got married at that point. I moved to Florida and joined a small venture capital. The focus of the firm was e-health. It was healthcare technology investments and was incubator-esque.

They got very engaged operationally with the investment. That’s what really appealed to me. I wanted to get more hands-on. As any associate of a venture capital does, I did lots of sourcing. Additionally, they had me go learn about the operational aspects of companies. For a period of time, I would take on a Director of Operations or a Director of Finance where they would have me move and take office with the portfolio company for a period of time. That’s what really appealed to me. I did that for about two years. It was after the crash. They were trying to help companies be successful. I saw a lot of great things and saw just as many bad ideas. Ultimately, that pushed me to the next step. I watched these entrepreneurs trying to build things and build value. More times than not, it felt like there was this discrepancy between what the entrepreneur was trying to build and what they could operationally deliver.

An example would be one of the investments that the firm made was with a company that was building an online medical supply distribution company. They hired these engineers who would close themselves into a room and lock the door. They would say, “We’re not coming out until this is done.” Then you walk by and you hear them playing ping-pong or pool. They consumed a lot of investment and ultimately, didn’t really deliver on the promise of what was espoused. I became disillusioned with venture market and with these venture-backed companies. I was equally frustrated with these programmers who were espousing this magical capability of code. I knew how to code, but I wasn’t great.

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
. Bootstrapped eGroup to $20M in Charleston, South Carolina
. Gravitant CEO Bootstrapped Using Services to $15M in Venture Capital
. CEO Bootstrapped Sitecore Using Services from Denmark
. Co-founder Dan Hermann on Bootstrapping Paint Nite
. Founder Krishna Kumar Bootstrapped App Orchid Using Services
. Bootstrapping a Web Hosting Company to $60M
. Bootstrapping CloudSense with Services on Force.com from London
. Bootstrapped Book E-Commerce Business BookPal
. Student Entrepreneurs Bootstrapped a Zero-Logistics E-Commerce Company to $19M
. Bootstrapped to a High Growth Inc. 500 Company
. 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
. Bootstrapping LittleThings First, Raising Money Later
. Bootstrapping eMazzanti Technologies Using Services
. Reltio Founder Bootstrapped Using Services
. Co-founders Bootstrapped Ateb Using Services from North Carolina
. Bootstrapped HireVue While in School, Raised Money Later, All in Utah
. Bootstrapping the First Venture, Raising Money for the Second
. Co-founders Bootstrapped BeenVerified with Angel Money
. Bootstrapping a Significant Software Company from Australia
. Bootstrapping Meltwater to $200 Million
. Bootstrapping Casewise from London and Scaling in the US
. Bootstrapping Lessons Learned by FairWarning Founder Kurt Long
. Abacus Group Founder Bootstrapped a Virtualization Services Company

Hacker News
() Comments

Featured Videos