Best of Bootstrapping: Lessons from Startup Mentoring Since 2008

These days, everyone seems to be a startup mentor. Whether they have ever done a startup or not, whether they have ever raised money or not, they are ready to advise entrepreneurs. I want to share with you some things we have learned in running the 1Mby1M program since 2008. Over 680 free mentoring roundtables. Over 300,000 entrepreneurs have participated.

We started experimenting with the roundtable format of online mentoring way back in the fall of 2008. At the time, 1Mby1M did not exist, not even in our heads. It wasn’t until my January 2010 New Year’s Resolution that the concept was born.

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Best of Bootstrapping: Bootstrapping an Enterprise Software Business for 30 Years

Dean Guida, CEO and Founder at Infragistics, has a real passion for the elegance, simplicity, and beauty of software development. He has built a company celebrating these values and shared his story with me in 2021.

Sramana Mitra: We will start at the beginning of your journey. Where are you from? Where were you born and raised?

Dean Guida: When I was six years old, my mom and dad got divorced. I moved to Miami, Florida. I saw how much my mom struggled to make money for us. When I was eight years old, I just wanted to work. I convinced the maintenance man in the apartment that I was living in to let me do his work. He would pay me off the books.

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Best of Bootstrapping: Pre-Seed Fundraising is a Low Probability Game

For our Seed Capital series of podcasts, I’ve interviewed hundreds of investors, especially micro-VCs and angels who play an important role in the early-stage game. The toughest round of funding an entrepreneur will seek to raise is Pre-seed. How do you increase your odds?

Pre-seed has the lowest probability of success. Over 99% of the entrepreneurs who seek financing are rejected. Read more about the Probability of Pre-Seed Funding.

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New Generative AI Customer Support Case Studies Course + Discounts

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Best of Bootstrapping: Serial Entrepreneur Bootstrapped First, Raised Funds Later

JobNimbus Co-founder and CEO Ben Hodson is a serial entrepreneur with a long experience in bootstrapping and fundraising. He shared how he has navigated his journey with me in 2021.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

Ben Hodson: I say that I am from the Seattle area. I was born in Washington State on the east side of the state, but I moved to the west side when I was very young. I went to the University of Washington. I got a degree in business. Then I was interested in computers, so I did a second degree in computer science as well.

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Best of Bootstrapping: Bootstrapped a New Age AI Services Venture

CEO Anji Maram has bootstrapped CriticalRiver to $50M in revenue and is introducing AI into his services business model. We expect to see a lot of this happening all over the tech services ecosystem. AI Services is going to become a massively valuable category.

Sramana Mitra: All right, Anji, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of background?

Anji Maram: I’m originally from India as you can tell by my name. I’m from a small village in Andhra Pradesh in South India. It has a very small population that is pretty much into farming community. My parents did not study, my siblings did not study. I somehow ended up studying.

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Best of Bootstrapping: Positioning Drives Velocity

VCs are salivating over ultralight startups right now. The stigma around solo entrepreneurs will vanish soon. Positioning will remain key to achieving Velocity. And Velocity will continue to drive Fundability.

Are you trying to raise money for your startup and getting rejections? It’s worth understanding WHY. VCs are looking for Velocity. Their goal is to achieve $100M in revenue in 5-7 years. How do you do that? You can read more and dialog here on what drives Velocity.

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Best of Bootstrapping: Bootstrapped with Services to $10M and an Exit

Among the biases of the Venture Capital industry that need to be categorically ignored, Bootstrapping Using Services happens to be on the top of the list. Zimit Founder and co-CEO James Cramer shared yet another fantastic textbook case study when we spoke in 2021. Zimit was acquired by Workday in September 2021.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

James Cramer: I was born in Southern California. I grew up in a family that moved around a lot. My dad worked in the automotive industry, and so every few years we would change locations. That put me in Seattle, Southern California, the Carolinas, and then ultimately in Florida.

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