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Best of Bootstrapping: Best Tactic for B2B Startups

Posted on Friday, May 29th 2020

What is the best bootstrapping tactic for B-to-B startups? Solve an acute customer pain. Get paid an advance to do so. Leeyo Software CEO Jagan Reddy followed this strategy to bootstrap to $20 million. He built a niche software that solved a very specific problem and started selling it to enterprises for a lot of money. This story is a textbook case study of how well you can scale with no outside financing if you can identify a burning pain point in customers who are willing to pay a LOT to solve that pain.

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

Jagan Reddy: I was born in India. All my schooling was done in India.

Sramana Mitra: Where in India?

Jagan Reddy: In Chennai. My schooling was all done in Chennai.

Sramana Mitra: Where did you do college?

Jagan Reddy: Guru Nanak College in Chennai. My education was mostly in the accounting field.

Sramana Mitra: What did you do after you finished college?

Jagan Reddy: I actually had a parallel education. While studying accounting, I was also doing some IT type of training. Once I came out of college, I started working for a well-established company in India called Goodrich. They specialize in a lot of different products, ranging from manufacturing to cosmetics. I joined them in 1996 to support their ERP implementation. I was part of the finance side of the ERP implementation.

Sramana Mitra: How long did you stay there?

Jagan Reddy: I stayed with them for three to four years. I traveled across India trying to implement the software. Then I worked for another company in Bombay. I worked there for a year.

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

Jagan Reddy: Around 1999.

Sramana Mitra: What did you do in 1999 after you left this company in Bombay?

Jagan Reddy: The company had a project for me in the US. I came to the Bay Area for that. I spent three months on the project and impressed with my work, my project was extended to almost two years with the same client. After two years, I decided to come back to India.

I had a job offer from Juniper Networks, a leading networking equipment manufacturer. This happened in 2001. I decided to stay in the US and took the job with Juniper Networks. My job was all about accounting-related software and supporting the IT in finance. I spent almost eight years there. I worked there from 2001 to 2008.

Sramana Mitra: Then what happened in 2008?

Jagan Reddy: Juniper went through a major shift in their business model where they were challenged with a lot of revenue recognition and accounting automation issues. They asked me to go and find a software that they can use and implement for their automation. I did a lot of research, but I couldn’t find a software that could help automate what they were looking for. In that process, we decided to custom-build for Juniper. I went and built a custom solution for Juniper, but it was all tailored to Juniper’s requirements.

Since I was researching the market, I figured out that there’s no software that could solve the complexity and I also understood that the issue was there for other customers as well. It was not just for Juniper. I did more market research. I talked to several companies. I understood the challenges and why they are not able to automate this, and why the ERP vendors are not able to provide a solution that cannot meet all this. I understood the complexity in doing this automation.

Our discussion 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

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