I advised him against it. No digital concept is going to beat that customer experience.
They had a basic website that outlined their general terms and bikes on offer etc, but then actually arranging the booking dropped into WhatsApp which allowed me to outline my specific needs and get a useful steer. Throughout the trip I was able to continue messaging as things came up and it felt more like I was borrowing a bike from a mate than renting one from a business.
At a higher level, this small business offered multiple channels and was able to meet me where I wanted to communicate. This is an advantage small business have because the volume is manageable. At larger scale it becomes more tricky to do economically and so you need to focus on self serve journeys (which may include chat bots, etc)
I get emails on a daily basis and people take that moment to give positive feedback, occasionally bug reports, and I get to see their email signature to get a sense who my customers are.
It’s genuinely enjoyable interacting with customers and most people are so easy to get along with if you just listen and show respect.
Another benefit of this approach is it’s simply much easier. If you’re trying to act like some smooth corporate salesperson or be overly formal or whatever and that’s not really you, interacting with customers and prospects and… everyone… will feel tiring and painful.
But if you drop the pretense and just act like yourself? Minimal extra energy required. As a bonus, it opens you up to make real connections with people who you click with as you run your business.
So it works, it’s easier, and it’s more fun. And has basically no downsides. But still something that most founders seem to have to learn the hard way for some reason.
Speaking authentically and admitting you don’t have all the answers is genuine, not weak. That kind of honesty has always worked best for me.
People respond better to real conversations, concrete examples, and the feeling that you’re building with them, not just selling at them.
In my experience, working with smaller businesses has opened more doors than chasing big corporate clients. Smaller companies tend to be more curious, open to new ideas, and quick to take action.
That said, “dress to impress” can work, but in my experience, it’s often a short-lived win. It grabs attention, but rarely builds lasting trust or real traction. Not a playbook I buy into.
For example, I recently sat through a 3-hour pitch from a so-called “AI consultant.” The presentation was packed with buzzwords, vague promises, and a sleek slide deck. Every time someone asked how AI would actually solve a specific problem, the answer was basically: “AI will handle that,” followed by name-dropping a popular AI company like it was the solution to everything. It was clear the consultant didn’t fully understand the tech, but the leadership team still ate it up.
This article was a great reminder that trying to sound big and impressive might get attention early on, but it often backfires later. Being honest and straightforward has always been my real strength, even if it keeps me small.
So yeah, you're a little company, act like one.
Nope, it was always stuff like: we need to do another grand redesign because we want to change our brand look and feel again.
One seed startup (where I had our prestigious flagship enterprise customer running with thus-far-perfect uptime in critical production, but we needed a second customer before we could raise), and which was down to a few people, I tried to convince a biz person to let me pitch in on sales.
(Seeing as how, although I dislike doing sales, it was what most needed help right then, or there wouldn't be a business, and I could also use product insight into what actually resonates with customers. And I've done a bit of sales before, and my dad was an engineer-by-training salesperson (osmosis!). My mindset is I don't try to pretend I'm not a nerd. I instead convey that I'm genuinely aligned with their success, I'll listen and understand, and I'll deliver successful solutions like competitors can't.)
Nope, we need a glossy Web site including video. Biz person needs to reformat our security assurances document into a brochure before it can be handed over to prospect's IT for vetting. And biz person needs to introduce me on a customer call as "one of our software engineers" (when I was the only one, working the usual technical cofounder miracles). :)
Like all startups, there were many mistakes, but I think one of the mistakes that time was thinking we had to fake it till we make it, when that undermined our strengths. (Well, slick artifice fit some of our sales prospects, but we didn't land those anyway.)
In hindsight, I think we should've focused on presenting ourselves as an exceptionally skilled and credible team that is 100%+ committed to the pilot project being a success for that particular customer (and for our champions there).
Competitors' salespeople couldn't deliver that, nor fake it very credibly, and there wasn't yet an obvious enterprise CYA alternative (nobody ever got fired for buying IBM).
The only lesson to be learned from all of this is when you build your next company, don't allow these people in. I'll keep beating that drum to eternity, because I saw first-hand how the work of tech people is leeched off by so many.
Everyone should be focused on the shared goal of the startup being successful.
What you're working on is triaged constantly, with everyone contributing what they can, learning as necessary.
Everybody wins, or everybody loses. And if you don't work together as a team, it's probably the latter.
(These are not just empty platitudes. For example, when I say everybody wins, that means I expect everyone to have meaningful equity shares -- not a successful exit makes the founders filthy rich, while everyone else gets a small consolation prize for contributing.)
Behind the anecdote, there were unusual and complicated reasons that someone felt and did some things as they did. I tried to carve out a standalone piece for HN, without getting into the more sensitive and irrelevant stuff.
But I suspect that early adopters are different for AI companies than technology infrastructure: AI early adopters want the benefit, but have no insight into how to push things forward.
So if there is backflow of information from your customers, exactly what information do you need to improve?
I'm the sort of client that wants to help you improve your product, and can - if you'll let me. When I'm allowed to talk directly to engineers (possible at small companies, vanishingly rare at large ones), we both end up better off.
I've seen the whole cycle, though, and it gets frustrating. Small and ambitious company works closely with me to build something really great; raises money / goes public / gets acquired; early employees cash out (good for them!) or get outsourced (disastrous choice); development stalls and features break. Now I'm back looking for a new small company to work with again. It's dispiriting, and so, so wasteful.
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