Hey, Aaron here! Welcome to this bi-monthly startup newsletter. In each write-up, I tackle questions about building products, financial planning, growth, and raising capital! Today, we dive into -

Education:

How much capital you should raise for your startup

Opinion:

Equity is forever — vet your team like your future depends on it

In the early days of building a startup, you're likely to get help from all kinds of people. Some will be genuinely helpful. Some will be great — but only for a certain stage. Others might look useful at first, but end up causing more harm than good. And a few are flat-out wolves in sheep’s clothing.

Founders get this wrong all the time — and I’ve seen it cost people more time and money than you can imagine.

When you’re in the early stage, it's easy to feel grateful for anyone who’s willing to help. You want to believe in people. You want to move quickly. And often, you’re just relieved someone said yes, but speed without judgment leads to real regret — especially when equity is on the table.

People Come and Go — But Equity Stays

You’ll likely work with dozens of real or potential advisors, contractors, random collaborators, and maybe even potential cofounders. Some will stick with you for years without a single document signed or a request for compensation. Others will drift and send you mean messages if you don’t say exactly what they want to hear. And a few will vanish the moment things get tough or boring.

That’s fine. It’s part of the journey – count on it and realize it’s not a mark of failure, it’s a step towards progress.

But giving equity to the wrong person? That’s really not fine. That’s permanent – and it can have major impacts on adding new team members or bringing on investors in the future.

Equity given is rarely — if ever — recovered. Imagine you give 2% equity to someone early who doesn’t deliver and doesn’t leave, and the business eventually works… that 2% becomes real money. A $100 million business means you just lost $2 million. And you’ll feel it. Every time you raise. Every time you do founder math. Every time you see their name on the cap table.

You can always fire someone, but you can’t fire equity.

Vet for Alignment, Not Just Talent

When you’re evaluating someone — whether as a cofounder, executive, advisor, or service provider — the most important question isn’t just “can they do the job?” It’s “Are they aligned with the way you’re doing the job?”

At the early stage:

• You don’t have time to babysit.

• You don’t have money to overpay.

• You don’t have room for ego, confusion, or misalignment.

Anyone joining at this stage needs to understand:

• You need to be scrappy as all resources are limited.

• Equity has to be earned, not expected / given.

• The collaboration is for the long term, not a short-term flip.

If someone’s not aligned on those basics, then it doesn’t matter how talented they are — it’s going to be a problem.

Work Together First, Commit Later

Before you hand over titles, responsibility, or ownership: work together. See how they operate. Test collaboration. Watch how they respond when things don’t go smoothly. If you haven’t seen someone mad, you shouldn’t bring them on the team. Something’s going to go wrong in your startup at some point, and when the pressure is on, you want to see what’s underneath when they eventually crack. For some people, it’s a warrior spirit who looks for the team win no matter what, for others, it’s them looking for a life jacket and abandoning ship without ever looking back. Ask yourself:

• Do they communicate clearly?

• Are they collaborative or defensive?

• Do they add momentum or drain it?

• Do they take ownership or wait for permission?

Give it a few weeks. Sometimes, even a few months. This isn’t about being slow — it’s about being smart. Anyone worth building a company with will respect that.

My Takeaways / Next Steps (if I’m a first-time founder)

• Take your time. Don’t rush into giving equity, titles, or major responsibility. Work together first.

• Vet for alignment, not just skills. The best people at this stage understand the grind — they don’t just want upside.

• Be clear about expectations. Document scope, timelines, and what’s being exchanged (especially when equity is involved).

• Differentiate long-term partners from short-term help. You don’t need your Fiverr contractor to buy into the mission — you just need the work done right.

Bottom line:

People may come and go — that’s normal. But equity is forever. Be generous when it’s earned, but never casual. The wrong person with the wrong slice of your cap table will haunt you long after they’ve stopped contributing.

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Written By Aaron @(un)conventional Team