The Startup Lottery: Your Guide to Navigating Risk and Reward – Chapter 4

Prior to reading this chapter/ book, I hadn’t put too much thought into what it would be like to work at a startup. Whether that be as the owner/founder or an employee within the business. The author goes on to explain that working for a startup isn’t for the “faint of heart”. The hours aren’t 9-5, the days aren’t predictable, you probably won’t get a set routine or work tasks because you are having to wear more than one hat, etc. The author had a quote that stuck out to me: “Joining a startup should be done with purpose, not on a whim. Apart from the risks, you must also be prepared for the intensity of startup life” (Bessalel, 471). Bessalel then goes on to say how admirable it is to let a company’s mission and purpose drive your career choices.

Part of me struggled to read through this chapter without immediately thinking “nope, this is not for me”. I am someone who does not like risk and uncertainty. Not having a work-life balance, job security, and benefits like insurance or pay to offset that, immediately makes me nervous.

The author mentioned that early in his career, his “idea to solve” the problem was to find and team up with the entrepreneurs who thought of a solution he liked (Bessalel, 46). Specifically for Bessalel, that involved buying a franchise location. Thanks to that decision, Bessalel learned how to operate a business firsthand. The creator of the franchise had already made it past the proof of repeatability stage on the Proof Continuum and had a set market/customer base. Bessalel mentioned how new startups differ from the franchise he used to get his toes in the water; he had a head start in comparison and higher chances of succeeding. This example would be more suitable for me to get into working/owning part of a startup, even if it’s just a single store out of a chain of them. There isn’t as much risk, and I have a bit more control than starting a venture from scratch.

I want to close this blog post with some questions the author asked the reader to see if a start-up is right for them. Maybe you can get a better idea of whether startups are a good fit for you:

  • Are you okay working for a company no one has heard of?
  • Can you handle uncertainty?
  • How big is your ego?
  • Are you an athlete or a position player? (Can you wear multiple hats to fill in where you are needed?)
  • Are you comfortable working in an unstructured environment?
  • Can you live and breathe the mission?
  • When is the right time to join a startup? (For you)

I’d love to hear your thoughts on whether you think the startup life is something you’re interested in trying or if you have similar thoughts to mine. While this chapter was very nerve-wracking for me to put my shoes in, I am eager to see where he takes this section of the book.

  1. Bessalel, Gus. The Startup Lottery: Your Guide to Navigating Risk and Reward. Jones Media Publishing, 2023, pp. 46–47. ↩︎

5 thoughts on “The Startup Lottery: Your Guide to Navigating Risk and Reward – Chapter 4

  1. Hi Meaghan,

    Thank you for this honest and self-aware reflection—I really appreciated how you walked through both the appeal and the anxiety that startup life can bring. Like you, reading this chapter made me reflect on my own appetite for uncertainty, and I have to say: no, the startup life is not something I’m interested in pursuing personally. There’s simply too much risk and instability involved for me, and I know I have a limited threshold for prolonged uncertainty.

    Working in higher education, I often see students drawn to the excitement and potential of startups—but I also see many who, like us, value structure, security, and a clearer path forward. And that’s okay. Not everyone is wired for the startup grind, and that doesn’t mean we’re any less entrepreneurial in spirit—it just means we thrive in different environments.

    What I did appreciate about this chapter, though, was the way it encouraged a thoughtful and purpose-driven approach. Even if I’m not going to jump into a startup, I can still support innovation in other ways—through mentorship, research, or working with organizations that align with my values but offer more stability.

    I liked Bessalel’s example of entering through a franchise—it’s a smart middle ground for people who want to experience business ownership without taking on the full risk of building something from zero. That concept of “entry with a safety net” is something we often explore with students in our entrepreneurship programs too.

    The questions at the end were especially useful for self-assessment. They reminded me that it’s not just about having an idea—it’s about knowing your capacity, your personality, and the environment where you do your best work.

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    1. Hi Freddy,
      Thank you so much for this thoughtful response—I really resonated with your perspective. It’s so validating to hear from someone else who recognizes the allure of the startup world but also knows their own limits when it comes to risk and uncertainty. I completely agree: choosing a path with more structure and stability doesn’t make us any less entrepreneurial—it just means we’re channeling that spirit in different, equally valuable ways.
      I also appreciated your point about supporting innovation from the sidelines. There are so many ways to contribute to entrepreneurial ecosystems without being the one at the helm of a startup. Mentorship, research, and working within mission-driven organizations are all powerful avenues—and honestly, they often have a broader and more sustainable impact. I currently have a career in the administrative field, and for the longest time I considered myself “just an admin”. But over the years my perspective has changed thanks to the executives who have supported me and appreciate how I support them. By helping them, I help them do their job better and spend their time more efficiently. It may not be them creating a business, but I feel like helping them make university wide changes is a close comparison.

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  2. Meaghan, thank you for your honesty in this reflection—it really stood out to me. I think so many people romanticize startup culture without fully acknowledging the chaos, pressure, and personal toll it can take. Your reaction—immediate hesitation around risk and instability—was refreshingly real, and I deeply respect how you explored both your concerns and potential pathways that feel more aligned.

    The franchise example really clicked for me too. It’s such a smart middle ground, especially for those of us who want to gain hands-on experience without jumping into the deep end. Starting from a proven model with systems already in place offers a level of structure and predictability that still allows for growth and learning.

    I also loved how you ended the post with those self-assessment questions. They were a powerful reminder that entrepreneurship isn’t just about ambition—it’s about alignment. Some of the most successful people I know didn’t launch their own startups, but they’ve built lasting careers by supporting founders, leading within mission-driven organizations, or becoming intrapreneurs within larger institutions.

    Your self-awareness and balanced approach are an asset—not a limitation. I’m looking forward to seeing how you continue exploring where your talents and risk comfort level intersect.

    Warm regards,

    Brent Parker

    Owner – Resilience Repurposed LLC

    Graduate Student – WCU (M.E.I.L.E. Program)

    https://blog.resiliencerepurposed.com

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    1. Thank you for your kind comment Brent!

      I agree wholeheartedly that entrepreneurship gets romanticized, and for some it is this grand, great adventure. I try to remain open to all options and opportunities and keep an open mind. When reading these chapters especially, I don’t want to immediately shut an idea down just in case I can apply it somewhere else or help someone else with that information!

      The franchise option really clicked for me as a good middle ground option, like you said there are set processes in place that are not as intimidating as doing it on your own! I think your point on gaining the hands on experience is so valid, not all jobs provide experiences like that. Plus it is not as scary as figuring it out on your own, you can sort of test the waters with an option like opening a franchise. Part of me is tempted to see if that could be a good route for me to try, but I’ll just have to see where the wind blows me at this rate.

      I appreciate you considering my approach as an asset, it truly means a lot.

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