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Best of Bootstrapping: Discussing People vs. Market with Jon Staenberg, Staenberg Venture Partners

Posted on Monday, Feb 22nd 2021

If you have been bootstrapping and think you are ready for investors, you need to learn how investors think. First, please study our free Bootstrapping course and the Investor Introductions page. Then start looking for entrepreneur – investor fit. Today I introduce you to Jon Staenberg.

Jon Staenberg, Managing Partner at Staenberg Venture Partners, has been a Seed Investor in over 400 ventures over the last 30 years. Jon draws from his long background and discusses some of what interests him to invest in a startup. He also reflects on the question People or Market: Which takes priority? You can listen to a podcast of our conversation here or watch the roundtable video below:

Sramana Mitra: Tell us about the focus of your investments and let’s introduce you to our audience.

Jon Staenberg: I’m a little disappointed that it took 374 shows to get me on, but I’m glad to be here. I’m kidding, of course! Congratulations to you for doing this. It’s nice to be interviewed. I’m an old dinosaur at this point, having done this for some 30 years. I originally moved to the Pacific Northwest to work at Microsoft in the late 80’s and have been venture and angel investing for that long.

I’ve been a partner in funds. I raised two funds under an autonomous name and then joined a group out of LA called Rustic Canyon Partners where I was a partner was well. You asked specifically what the focus of my investments is. I don’t really have a specific geography or sector focus. Having done this as long as I have, there are some areas when it comes to pattern recognition and people who I’ve worked with in the past that I tend to focus on.

To be clear, I’m not sure I’m very good these days at keeping up with all the changing trends and all the differentiated and iterative kinds of companies being formed. When I started doing this, my focus was pretty clear. It was mostly enterprise software. It was a completely different game. There were fewer venture players. You put several million dollars to work and it would take a couple of years. Then you hope you’d figure it out and then you try and get a couple of customers with a long sales cycle.

That world, of course, has changed dramatically. While I remain active and excited, I would say that I’m much more opportunistic these days than I am focused on one thing. Having said that, I am currently excited and interested about several sectors. I do think that Blockchain-related activities are extremely interesting and significantly game-changing opportunities. Even if my background was in enterprise, it’s hard to ignore what’s happening in the cloud.

What I’m saying is I’m trying to build off all the things I’ve done. I’ve made well over 300 investments at this point. Hopefully, I can take some pattern recognition from those previous investments and apply it to the modern era.

Sramana Mitra: Tell us a bit about what has been some of your most interesting investments. In the 300 or so that you’ve invested in, what stands out and why?

Jon Staenberg: The thing that’s interesting to me is that I can honestly say you never know what’s going to work. I’m often surprised both downside and upside. I had a company that I thought would never amount to anything and it had over a $2 billion exit in the last 12 months. It’s pretty exciting.

Sramana Mitra: What company was that?

Jon Staenberg: SquareTrade. It’s in the warranty business. You probably have seen their ads.

Sramana Mitra: Yes.

Jon Staenberg: I was in that company for a very long time and had not expected that outcome. What was interesting about that one is, they had received a very significant investment a few years ago from a major private equity firm. That was not a traditional path and that private equity fund took it to the next level.

Back in the day, it was a pretty traditional path to an exit or non-exit. You did a Series A through C and then you either got acquired or went public. Today, there are so many different paths. It’s exciting, but it also has created a lot of noise or confusion in the marketplace.

Sramana Mitra: That noise is what we’re trying to help cut through and come up with some sort of a logic to understand that. I’ve been in this business for more than 20 years as well. I did three companies in the 90’s. In the 90’s, you used to do seed investment and then Series A.

Now you do pre-seed, seed, post-seed, pre-Series A. What is the difference between post-seed and pre-Series A? This is not so simple anymore to understand. For entrepreneurs who are doing it for the first time, it’s not easy for them to understand where they fit in.

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

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