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Best of Bootstrapping: Looking at Terms with Heidi Roizen of Threshold Ventures

Posted on Thursday, Mar 25th 2021

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

Heidi Roizen, Partner at Threshold Ventures, discusses her important article, “How to Build a Unicorn From Scratch – and Walk Away with Nothing,” and imparts crucial lessons to entrepreneurs on how to look at terms in a venture financing situation.

Sramana Mitra: We have been living in world of unicorn mania. We have tried to put some perspective on this issue. There are good sides to the unicorn mania. There are bad sides to the unicorn mania. Let’s start with one particular piece that you wrote, which I thought was very well-analyzed. The piece was titled How to Build a Unicorn From Scratch – and Walk Away with Nothing.

Heidi Roizen: I’ve been doing this for a long time, and I’ve seen cycles come and go. There are two things every entrepreneur should be aware of that they really aren’t aware of. One is, not everything goes well all the time. If you’re an entrepreneur, you fully believe that everything is going to go great for you. The reality is, that is almost never the case. The second thing is, our economy moves in cycles. The macroeconomic conditions will affect your ability to raise money and prosper.

If you take those two things in mind, what has happened and what created this unicorn problem is, entrepreneurs got very fixated on raising very large amounts of money on high valuation. First of all, money in a war chest seems like a good thing to have. Second of all, being able to talk about your billion-dollar valuation makes it feel like it’s a very solid company.

There’s a falseness under that because at the end of the day, venture capital is still debt. It is money you have to pay back in, pretty much, every circumstance. It’s preferred shares, and preferred shares, in essence, are debts that must be paid back first in any but a terrible outcome or an IPO where everything goes common. We can count the number of IPOs in the last year on not too many toes and fingers, so let’s not go that direction.

The reality is, the entrepreneurs have made this sort of deal with the devil. I guess I shouldn’t say that because it makes it sound like investors are devils. The entrepreneur says, “I want a really high valuation and I want to raise venture money. If I raise venture money at a high valuation, I don’t get diluted.” The investors says, “Okay but I want some downside protection. It’s hard for me to imagine your company is worth a billion dollars today. I’m going to put in preferred liquidation preferences and a bunch of terms.”

Entrepreneurs need to worry about that, because the terms are more important than the valuation. Here’s a fun example. I went to a party once and said, “I will make anyone a unicorn tonight. I will give anyone a billion-dollar valuation.” I had a term sheet and it was printed on my business card. It said, “I’m going to invest a dollar in you. I want a 100x on my money and I’ll give you a billion-dollar valuation.”

If you got to pay me $100 as return on my money, that’s not a very good deal for you. If you’re raising $200 million and there are ratchets and multiple guarantees on that money, you are in a very different place. This is why it’s taking me so long to answer the question. It’s actually very complicated. Particularly when there are multiple rounds of financing, everybody around the table starts to have different economics.

If your company sells for a billion versus half a billion, they’re still going to get double their money and then you have another person who doesn’t make a penny until after you sell for a billion. Those people are going to have very different economics. The one thing entrepreneurs should remember is, unless you are in a highly unusual situation, you sit at the bottom of the stack. You sit below everyone else who has invested money on whatever terms in your company. I just think entrepreneurs need to keep that in mind. I really believe that clean and simple terms at rational valuations are the best healthy hygiene for any normal company that is out there to raise money.

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

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