Spoke to hundreds of businesses in last 4 years, here's what I learned
Over the last 4 years I have spoken to hundreds of companies.
Here is what I learned:
#1 - Tech fatigue is real
People are tired of trying to figure shit out all the time, they just want someone competent to tell them what to do.
#2 - Your site design doesn't really matter
I've used SaaS applications with crap UI and UX who are making millions a year. Stop obsessing about this. It means nothing.
#3 - B2B sales happen during calls
If you're selling B2B and NOT regularly jumping on calls with your clients - you're doing it wrong. Calls with your clients are how real relationships are built and where B2B sales happen. You just need to know what you're talking about, be friendly and professional.
#4 - Email marketing is broken
The complexity of email deliverability is too much for the average business owner. SMB's hit the hardest. Gmail and Outlook are silently killing your business and you don't even know it.
#5 - Honesty and competence is a super power
People are so tired of salesly BS, that you can build insane trust and loyalty if you're just brutally honest about what you can't do, or what you don't know.
#6 - Stop trying to sell
During discovery calls, stop with the standard salesly BS, start helping them right away and talk about how you're going to fix their problem and what success looks like. I perform tests with clients live on the call and start giving them free advice even before they paid. I close 90% of discovery calls like this.
I probably missed something, feel free to comment.
Replies
I also think a lot of founders overestimate how much design matters before the core problem is even solved. Do you think clarity usually beats polish in the early stages?
Hello Inbox
@sadie_charlotte1 100%. Think Google, Wikipedia, Reddit, Amazon. Not the most polished sites, but they're huge. I would add utility to the list. Clarity + Utility wins over polished design.
The honesty point hit hardest for me because people can usually tell pretty fast when someone is trying too hard to "sell." Do you think trust closes more deals than persuasion in B2B now?
Hello Inbox
@reid_anderson4 100%. You can be persuasive without being overly aggressive. Being direct (honesty) + knowing your subject matter (competence) = trust.
The email point is painfully real because so many small teams think "we sent it" means "people saw it". Do you think deliverability is still massively underestimated?
Hello Inbox
@wyatt_cameron Oh yes, massively. I still have calls with marketers who are "just getting their heads wrapped around this deliverability thing". Marketing agencies. Think about that for a minute...
What stands out here is the most of these lessons are less about tactics and more about reducing friction for the buyer. Was there one lesson that surprised you more than others over time?
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@alyssa_monroe Yes, one. It shouldn't have surprised me in the end because it's kind of obvious, but just being honest and open with people reduced so much stress and built relationships with people. I thought I would be judged on the fact I was just a 1 man show or I didn't have a "real office". I'm a digital nomad and live in various countries. I never tried to conceal anything, I think people, especially other business owners and marketers have a huge BS detector and can smell it a mile away. They really appreciate someone who can get down to business right away, not waste time and is open and transparent.
Great advice and insight. Thanks for sharing especially point 6. Often times sales jump straight into a pitch without really understanding the pain points of the potential customer. Hear them out and figure out how you can them and a budding relationship will form.
Hello Inbox
@calvin_lim_1 Yes, #6 is a big one. It's almost counter-intuitive, but it works very well.
The email marketing part is interesting. Deliverability has become way more complicated in the last few years. Many businesses think email is dead when it’s actually a setup problem
Hello Inbox
@anil_yadav38 Waay more complicated. Setup, Authentication, Reputation, Content, List Hygiene, etc. Google and MS have attained such an insanely large market share in the last 10 years that basically deliverability comes down to 2 companies. Even someone who's done "everything right" still finds their emails going to spam or promotions.
This resonates deeply. Four patterns I have noticed from talking to ~200 potential users while building Hello Aria (AI productivity assistant for WhatsApp/iOS, launching PH April 10th):
1. Businesses know their problem, not their solution. They describe pain, not product specs. Ask about pain first.
2. The person you talk to and the person who will actually use it are often different people. Both need to be convinced. Budget holder and daily user are two different conversations.
3. "We tried something like this before" is not an objection — it is a treasure map. What failed? Why? That's your product edge.
4. Silence in a demo is usually confusion, not contemplation. Build for zero-confusion demos. Anything that requires explanation is a product problem, not a communication problem.
What is the most surprising thing you learned that changed how you build or sell?
Hello Inbox
@sai_tharun_kakirala good insight. Can confirm 1 and 2. What changed for me is I now build solutions to personal problems. Solving a problem for yourself and being your own customer gives you a significant edge over your competitors.