Even the Best Entrepreneurs Can't Rush Trust
Entrepreneur Office Hours - Issue #295
I’m prepping this newsletter after spending the past couple hours triaging my email inbox. For whatever reason, it contained a particularly large number of emails from random entrepreneurs asking for me to become advisors in their companies, or invest in their companies, make intros for them, etcetera.
I always chuckle when I get those types of emails because clearly they’re entrepreneurs who just don’t get that getting someone to help you isn’t as simple as sending a cold email and asking. You have to build trust over time. That doesn’t happen with a single email. Or even a single meeting.
In fact, one of the most frustrating patterns I see with early entrepreneurs is how they expect the first meeting with a potential investor, customer, or partner to be the meeting where the deal gets done. They walk in, deliver their pitch, and assume the other person will immediately say, “Wow, you’re amazing! Here’s my money/time/reputation — please take it.”
Ummm… no. That’s not how things work.
Sure, you believe in yourself. But the people across the table? They don’t know you from Adam. Why would they risk their money, reputation, or social capital on someone they just met? They won’t. Not yet.
That’s because trust doesn’t come from a single conversation. Trust is built over time, through repeated actions that consistently prove you’ll deliver the value you promise.
This, by the way, is what a brand is. I might walk into a Mercedes dealership for the first time in my life and buy a car on the spot — not because I’ve personally tested their cars, but because I already trust the brand. It’s been built over decades of delivering on expectations.
When you’re running a small, early-stage startup, you don’t have that luxury. You can’t fast-track trust. You have to earn it. And earning it means showing up, delivering on small commitments, and doing it again and again until the person on the other side feels as confident in you as you feel in yourself.
The good news? If you stick with it long enough, your brand will start doing some of that work for you. Until then, patience isn’t just a virtue — it’s part of the sales process.
-Aaron
This week’s new articles…
The Mistake Every New Entrepreneur Makes (Even My 9-Year-Old)
Some startup strategies are so instinctual, even a child defaults to them. But that doesn’t mean they’re good strategies.
Is the Biggest Threat to Your Startup Lurking in Your LinkedIn Feed?
A simple coffee meeting with a founder became a reminder of what so many entrepreneurs quietly struggle with.
Office Hours Q&A
QUESTION:
Hi Dr. Dinin,
I’ve been working on a small product-based business for the past six months. I mostly sell through Instagram DMs and word of mouth. It’s going okay, but now I’m getting asked more and more often if I have a “real” website.
I know it’s probably time to build something more official, but I have no idea what kind of site I actually need. I realize you focus more on big companies and maybe this question is too niche, but I thought it’d be fun to ask.
How do I figure out the right kind of online presence for my stage of business? Is there a rule of thumb you use?
Even if you don’t decide to answer this question, I still appreciate all your insights that you share. Your no-nonsense advice is some of the best out there, even for an entrepreneur like me who is never expecting to raise millions.
—Carmen
This isn’t a niche question. In fact, it’s one of the most universal questions I get. Whether someone’s selling art through DMs or building enterprise software with $20 million in VC funding, eventually everyone starts wondering: “When is the right time to move to the next level?”
And the truth is… there’s no big magical moment when someone shows up and declares you ready. Usually, leveling up just starts with exactly what you’re feeling: small hints. A few more requests. A few more frictions. A few more people asking questions like: “Do you have a website?”
In those moments, the temptation is to overcorrect and jump straight from “selling in DMs” to “I need a full-blown Shopify experience with custom branding and six email flows and a logo that looks good on tote bags.” That’s how people end up spending more time trying to look legitimate than actually being legitimate.
But leveling up doesn’t mean rebuilding from scratch. It means smoothing the edges of what’s already working. If customers are asking for a website, that doesn’t mean you need to become a tech company. It just means you’re ready for a checkout link. Or a landing page. Or a simple place people can click buy without needing to message you first.
That’s all a website really is — not a monument to your brand, but a tool to make it easier for people to pay you.
And here's the real kicker: you’ll go through this same cycle over and over again. Not just with your website, but with every part of your business. Your products. Your packaging. Your customer service. The questions won’t be, “Do I need to do this?” They’ll be, “What’s the smallest next version that actually helps?”
Do that enough times, and before you know it, you're not asking how to look official anymore. You just are.
Keep going. You’re already further along than you think.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.