Since we are close to wrapping up for the semester, I decided to skip Chapter 6 due to it being short and more about how to accept a job at a startup. While it is a good chapter, I thought this one would be a better finish to wrap up the semester.
Chapter 7: Look the Horse in the Mouth
This chapter not only caught my attention with the interesting title choice, but also due to the interesting take on how to know if accepting a job at a startup is for you. This chapter is all about how an individual being offered a job at a startup should evaluate the company like a VC or angel investor would. The chapter starts off by comparing the risk of joining a startup and funding one, “The risk you take on is directly related to how early you join a startup… Sometimes the best you can do is determine if a company has the resources to survive long enough to reach its next funding round and eventually figure out a market opportunity that leads to a successful exit” (Bessalel, 1111). While there may be a bigger chance of you gaining more out of working/funding an early-stage venture, the individual is taking on an even bigger risk of it not working out. Studies on the subject range anywhere from 75-90% of startups failing (Pollman, Harvard Law School2).
I thought Bessalel’s perspective on this was really insightful. I agree that if investors are encouraged to ask questions and gather more information to assess risk, employees should have the same opportunity to learn about a company before deciding if the risk is worth it for them. We’re often told to research companies when applying, but beyond surface-level info, most people genuinely want to understand what they’re stepping into. I recently accepted a new job, and one of my main goals during the process was to figure out if it was a good fit. I enjoyed my previous role, and based on the job description, I assumed the new position would be similar, or at least offer ways to grow the skills I already valued. I didn’t want to risk leaving something I enjoyed if this didn’t seem like a good match for me.
“The difference between you and a VC is that your portfolio of companies consists of only one investment. When you choose to work for a company, you make a venture capital bet with your time. Every day you get up and go to work for that company, you are making an investment and hopefully earning a return and positioning yourself for additional future returns. You can’t rely on other companies to bail you out if your one portfolio company, your employer, fails. It’s an all-or-nothing gamble”
– Bessalel, 115
I like how the author used this chapter to remind the reader that they bring value to a startup. I think the areas Bessalel touched on can be applied to non-startup jobs as well. Bessalel recommends looking at the company’s health, sustainability, overall potential for success, and the Proof Continuum, focused on in this blog post, as a starting point to evaluate the company like a VC (Bessalel, 113).
I am curious to hear your thoughts on this and if there are any other considerations a new startup employee should consider. Thank you for reading my blog throughout this semester, I hope to see you all in a future course 😊
References:
- Bessalel, Gus. The Startup Lottery: Your Guide to Navigating Risk and Reward. Jones Media Publishing, 2023. p. 111-113. ↩︎
- https://corpgov.law.harvard.edu/2023/09/29/startup-failure/ ↩︎
Explore Entrepreneurship & Innovation 
Hi Meghan,
I really enjoyed your blog post and completely agree with your approach to researching a company before accepting a job. I did the same thing before accepting my current position, even though the field of research administration was completely new to me. I had never worked in this area before, but I brought several transferable skills and had a strong research background from my time as a student at WCU. I was already deeply involved in the community and had built relationships with local foundations and many faculty and staff at the university, which helped me better understand the role I was interviewing for and WCU’s culture and values.
During the interview process, I made it a point to ask questions that would give me a clearer picture of the role, the team dynamic, and why the position had been vacant for so long. I also asked about potential growth opportunities because I think it’s important to know not just where the job is starting, but where it could go. I see interviews as a two-way street, where I am interviewing the company just as much as they are interviewing me.
You asked what other considerations a new startup employee should keep in mind. I think that is a great question. One big thing is understanding the company’s vision and whether it is clearly defined, realistic, and achievable. In a startup environment, things move fast, and responsibilities can shift quickly, so it is important to know if you are comfortable with ambiguity and wearing multiple hats. Also, getting a sense of the leadership style and communication norms early on can help determine if the environment will be a good fit. Lastly, clarity around expectations, metrics for success, and how feedback is given can go a long way in helping a new employee thrive.
Thanks for sharing your perspective!
LikeLike
Hi Samantha,
I did the same thing for my current position. I have always been told that an interview goes both ways, both sides need to interview each other. Not only do you as the applicant need to impress the interviewer(s), but they need to impress you to keep your interest. Having served on a few search committees while at WCU, you can always tell the people who did their homework versus who didn’t. That goes for both sides of the process as well. If a candidate doesn’t have any questions or questions that don’t show a true interest in the role, they typically don’t make it to the final round. If a candidate were to ask questions like the ones you listed in your previous interview, those would register as a green flag that you are truly interested in the role in my opinion.
I like your advice to take note if the vision is clearly defined, realistic and achievable. You are exactly right that in such a fast paced environment, it is easy to forget the big picture versus what is right in front of you. I feel like that isn’t something that is a ‘standard’ question in ask in an interview setting.
Thank you for providing such valuable feedback this semester Samantha!
LikeLike
Hi Meaghan,
I really appreciated your take on this chapter — you did a great job highlighting how Bessalel reframes the traditional job search mindset. I agree completely that prospective employees should evaluate startups the way VCs do. After all, when you join an early-stage company, you’re investing your time, energy, and career trajectory — and that’s just as valuable as capital.
Your point about most people wanting to understand what they’re stepping into beyond surface-level research really resonated. It’s one thing to read a job description and company website, but it’s another to dig into the company’s runway, leadership track record, customer traction, and even internal culture. I think things like founder transparency, clarity around growth plans, and how success is measured are also critical to evaluate.
Congrats on the new role, by the way! It sounds like you approached that decision with a healthy mix of curiosity and caution — which is smart. I’d add that another key consideration for startup employees is equity: not just how much you’re being offered, but what it actually means (vesting schedule, dilution risk, exit potential, etc.). Too often, startup equity is overpromised and misunderstood.
Best,
Freddy
LikeLike
Thank you so much Freddy! I am coming up on being there a month and it definitely still feels like the best choice for me. I feel more aligned with this position than any other role I have had in the past. Hopefully it’s not the shininess distracting me, but I am very optimistic that it will only go up from here!
I like all three suggestions you made for those considering starting a jo with a start up, but your point about equity. I have definitely heard horror stories of new people in a field being promised all the bells and whistles, then end up not getting what they signed up for. With a lack of clarity on what those bells and whistles fully meant, it ended up not benefiting them at all. Those misunderstandings can lead to many issues down the road, so it is a great idea to get that clarity upfront!
Thank you for engaging comments this semester!
LikeLike
Hi Meaghan, your personal anecdote about wanting to understand if your new job was a good fit goes directly to the heart of Bessalel’s argument. It is not just about the job description; it is about assessing the company’s health, sustainability, and potential for success, just as an investor would. The comparison to the high failure rate of startups, as noted by Pollman, really underscores the inherent risk involved, making the due diligence process for a potential employee even more critical.
Also, Bessalel’s quote about your time being an “all-or-nothing gamble” is incredibly powerful. It captures why employees should empower themselves with information, pushing beyond surface-level research to genuinely understand the company’s trajectory and the risks they are taking on.
GaVonne
LikeLike
Thank you for commenting GaVonne!
I agree whole-heartedly about the “all-or-nothing gamble” quote. Jobs are not just jobs, they are someone’s livelihood, purpose, where they spend most of their time, etc. I find that it is rare to take a job solely based on what the role does these days, I know many who have to factor in things like benefits, hours, childcare, etc. When you don’t have the information upfront, it’s hard to make an educated decision.
LikeLike