Unlocking Startup Success: Insights from 200 Entrepreneur Questions
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Chapter 1: The Journey of Teaching Startup
On May 1, 2020, I launched Teaching Startup beta, a project aimed at making startup guidance accessible, affordable, and practical for all. Now, as we celebrate the release of Issue #100 of our newsletter, I've had the privilege of responding to over 200 questions from entrepreneurs at various stages of their journeys, from novices to seasoned founders.
This experience has been enlightening, revealing why many startup advice platforms often fall short of helping entrepreneurs. Originally, Teaching Startup stemmed from my 15 years of experience as a formal advisor for numerous VC-backed companies. At that time, a select group of startups would pay me to leverage my extensive experience in building high-growth companies and products from the ground up.
However, around three years ago, I began sharing my insights on Medium, which garnered significant attention. While my formal advisory role could greatly assist a few startups, my writing reached millions, providing a broader, albeit shallower, level of support.
Teaching Startup was designed to bridge this gap. One critical insight I’ve gained about startup advice channels is that while they aren’t necessarily ineffective, they often lack efficiency. To effectively assist startup founders with their immediate challenges, I realized I needed to create a unique delivery method and collaborate with a different type of advisor.
If you’re a startup founder seeking guidance, you might resonate with this. After addressing numerous questions, let me share my findings and invite you to explore this approach for yourself.
Section 1.1: The Power of Diverse Perspectives
If you haven't yet explored Rachel Greenberg’s articles on startup and business growth, I highly recommend doing so. I’ve followed her work for some time but hesitated to invite her to contribute to Teaching Startup until recently. In this week’s newsletter, she tackles her second question.
Rachel, along with other vetted advisors like Lynn Walder and Rhiannon Monks, brings a fresh perspective that diverges from the typical startup narratives often glorified in mainstream media. She has built a successful career as an entrepreneur and advisor, but her approach is grounded in practicality rather than the Ivy League myths or the hype surrounding accelerator programs.
Rachel’s contributions, like those from Lynn and Rhiannon, offer actionable insights drawn from real-world experiences, encouraging you to think critically and take meaningful action rather than feeling excluded from the so-called “secret” of success.
Section 1.2: The Inefficiency of Motivational Advice
When I assert that much startup advice is not necessarily bad but inefficient, I’m referring to the fact that a lot of it is purely motivational. Often, it seems geared towards boosting the advisor's views and clicks rather than genuinely assisting you in growing your business.
This realization comes from my own experience—this post included. I recognize that to attract an audience, I often have to craft catchy SEO-friendly titles or emphasize commerce. If you’re not investing in advice, the guidance you receive may not meet your needs.
The truth is, motivation without actionable direction is futile. It becomes monotonous; when you’re attempting to achieve unprecedented goals, constant cheerleading can turn into annoyance rather than encouragement.
What I've learned from answering over 200 entrepreneur inquiries is that genuine assistance doesn't typically generate high engagement or fill your customer pipeline. Thus, I seek advisors who comprehend this distinction and understand when to prioritize meaningful guidance over mere clicks.
Chapter 2: Exploring Effective Startup Guidance
For those in search of focused startup advice, I invite you to try Teaching Startup, where we provide expert insights for just $10 a month—less than 1% of what a traditional advisor would charge. Use the invite code MEDIUM to enjoy your first month at half price.
The first video features a $30M founder addressing common startup queries, providing invaluable insights for aspiring entrepreneurs.
The second video discusses essential mindset shifts required for achieving a $10M+ business, emphasizing the need for strategic changes in approach.