August 19, 2025

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You make a hundred decisions every week that could change the trajectory of your business.

Pricing strategy. Hiring decisions. Product features. Partnership deals. Marketing investments.

Each one feels like a test where you don't know the right answer, but your grade determines whether you eat ramen or steak next month.

We all feel like we’re unique, but somewhere out there, someone has already taken this exact test. 

They know which decisions work, which ones backfire and which ones seem right but are actually traps.

One of the main points of this newsletter, as a whole, is to share stories with you so that you don’t have to learn the hard way. But there’s only so much I can do without knowing everything about your business.

Mentors, however, are people who you do tell all the details to. They come back with great, helpful advice, because they’ve been through it. They’ve seen this movie before.

By the end of today’s issue, you'll know exactly which type of mentor you need, how to find them and the steps to design a mutually-beneficial relationship with them.

In this newsletter:

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Weekly Insight

Sue Khim was building something people wanted. Even better, she was building something she wanted.

She dropped out of the University of Chicago to launch Alltuition, aiming to help students navigate the financial aid maze. Users were signing up. The team was motivated. Early traction was encouraging.

Her & her cofounders even got into the renowned startup accelerator, Y Combinator.

By all accounts, things looked good.

But during her time at Y Combinator, her mentors kept probing deeper, seeming to see something she’d missed.

They didn't dismiss what Alltuition was accomplishing. Rather, they pushed Khim's team to examine the fundamental economics of their model. Could they build something defensible? Would this create lasting value? How would the business evolve as the market matured?

These aren’t the kind of questions you naturally ask yourself when you're out there doing the thing. You’re busy executing and, if you’re nice to yourself, celebrating your progress. 

But they’re often the exact questions you need to consider. They’re directional questions: the kinds of q’s whose answers build a foundation for the rest of your actions.

Khim’s mentor conversations sparked a few months of honest reflection, then a strategic decision. She needed to pivot her team's focus to something with deeper potential.

It was undoubtedly a hard decision, but the right one (& a great example of failing forward).

The team’s pivot became Brilliant.org, the interactive STEM learning platform that now serves over 10 million users.

The transformation wasn’t easy, and didn't happen overnight. 

Khim spent months building relationships with education veterans, former teachers and data scientists who helped her understand learning theory and user motivation. 

More critically, these advisors challenged her assumptions about how people learn.

This led to genuinely useful conversations, which opened the door to deep insights, eventually landing Khim and her team on a valuable, future-proofed product.

Obviously this is ideal, but it’s ideal for a reason. Khim built relationships with people who understood her industry, had walked similar paths and were invested enough in her success to have difficult conversations when needed.

I’ll use the next section to help you get ready for those same types of relationships 👇

​​📚 Related Reading

Intent to Action

Entrepreneurs with mentors are five times more likely to launch their businesses compared to those without.

A survey by the UPS Store found that 70 percent of small business owners that receive mentoring survive for five years or more.

Mentors = good idea.

But a lot of fledgling entrepreneurs approach mentorship backwards. They wait until they're struggling, then frantically reach out for help. By then, they're more often seeking damage control than strategic guidance.

The best thing you can do is build out your advisory network before you need it. 

Step 1: Map your mentorship needs

Not all mentors serve the same purpose.

I think of business mentors in three distinct groups:

Peer mentors

Think of this as your core entrepreneurial community - other founders dealing with the same kinds of daily challenges you are. They provide real-time empathy and tactical problem-solving. 

Classic mentors

These are the mentors I’m aiming to help you meet. People who've successfully navigated the path you're on. 

They've built and scaled businesses in your industry or adjacent ones. Thus, help you see around corners and avoid expensive mistakes.

Executive coaches

These are professional (aka: paid) mentors who specialize in developing founders and business leaders. They bring structured frameworks to help you challenge your own assumptions, and have a vested interest in your success.

Step 2: Audit your current network

Write down everyone in your professional network who fits into one of those three categories. 

Don’t try to force people into buckets, either. Finding out who you don’t have access to is one of the most important parts of this step.

If you're drawing blanks on any of these, don't worry. Most entrepreneurs start with gaps. The point is getting clear on what you need to build, so you know exactly who to look for in the next step.

Step 3: Start with warm introductions

The best mentorship relationships develop organically through mutual connections. Don't cold-email strangers asking them to mentor you. Instead, ask your existing network for introductions to people who might be valuable advisors.

Frame your requests around specific challenges rather than general guidance. 

Rather than “I’m looking for a mentor,” try “I'm trying to figure out pricing strategy for a B2B SaaS product. Do you know anyone who's navigated this successfully?”

Step 4: Design the relationship

When mentorship relationships fail, it’s usually because expectations aren't clear. Early in the relationship, establish:

Remember that mentorship is a two-way street. Think about what you can offer in return: industry insights, connections to other founders or a fresh perspective on their current challenges. You don't need to lead with this, but keep it in mind as the relationship develops.

Most importantly, respect their time. Come prepared with specific questions and updates on actions you've taken since your last conversation. This shows you're serious about the guidance they're giving you.

Closing Thought

Most entrepreneurs wait until they're drowning to reach out for help. By then, they're looking for someone to throw them a life preserver, not advice on how to navigate the waters ahead.

Those who succeed, like Khim, build their advisory network before they need it. They cultivate intentional relationships with knowledgeable people, then let those relationships influence them.

Your next big decision shouldn't happen in isolation. The question is: who's in your corner when it's time to make it?

Next week, we’re getting tactical. I’ll be going over best practices for building a high-converting landing page.

See you then.