Investors Can See Your Chaos Before You Think They Can
I really tried avoiding working with startups as much as I could but I can’t anymore. Startups need me!
(Plus they're A LOT more fun to work with when they're not traumatizing you as an employee 😅)
Bold of me to say; I know, but I’ve seen some scary things.
I’ve sat in rooms where basic workflows were tribal knowledge and every decision bottlenecked at the founder.
I’ve sat in rooms where the entire company hated the team I supported because they lacked structure (I fixed that issue soon after I was brought on board).
I’ve been part of interview processes that were so chaotic the company accidentally invited me twice to interview for the same role.
That specific interview process was a nightmare from start to finish and deserves its own post for another day. However, I will say had I been an investor undercover, I would’ve pulled my money immediately.
Why? Because that level of systemic disorganization isn't "hustle"—it’s a major structural risk that is consistently punished in due diligence.
You might be thinking, “Well it’s just an interview.” That’s the problem: you’re not thinking enough….. and that’s probably why you still don’t have any investors but I digress.
People underestimate how often something like a recruiting interaction exposes deeper structural problems.
Your recruiting experience is an audit of your execution engines. Investors pay attention to it because it reveals:
➔ Founder dependency. If every step waits on the CEO to untangle something, the entire org moves at the speed of one person.
❌ That creates real scalability limits and real valuation risk.
➔ No operational maturity. Missed steps or repeated touch points signal that there are no documented workflows.
❌ Investors assume your sales and delivery systems are just as shaky which translates to revenue volatility.
➔ Burnout and ambiguity. If the process feels messy from the outside, the team is most likely dealing with even messier internal conditions.
❌ High churn is rarely forgivable right now.
This is the exact chaos I fix. I’ve been inside enough teams to know how much execution risk sits inside undocumented knowledge, shifting roles, and founder-run decision loops.
Scrappy isn't the problem. The absence of structure is.
If you want investor confidence, you need governance that proves you can handle the money you're asking for.
Don't know where to start? I’ve got you covered.
➔ Make your workflows, roles, and escalation paths auditable and repeatable
✅ https://bit.ly/48kTAoL
➔ Ensure internal processes and financial hygiene convey reliability and scalability
✅ https://bit.ly/48xN24S
➔ Onboard and hire with structure to protect runway and accelerate team performance
✅ https://bit.ly/3Mjb24n
✅ https://bit.ly/48mqhlH
2025 fundraising is basically over now but still you have a chance to fix your company for 2026 and your next raise.
Happy Thursday 🤸🏽♀️