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)
Spur-of-the-moment phone calls and meetings (especially camera-on ones with some uncaptured visual elements that the blind can't follow) tend to foul that up. And trigger the autistics who are likely hiding amongst the rest of you. We are legion. Treat us gently and we will likely do all manner of scutwork, refactoring old nasty untouchable code, and pager duty. i love debugging!
[Edit to add: Never trust a manager who likes to give directions in impromptu, unrecorded/unrecordable sessions. That means for some reason they want to be off-record. Or don't understand management. Either one of those is trouble.]
I'll add "they're functionally illiterate" to the list of reasons managers and other awful-to-work-with people default to "a quick huddle". I have no data but I suspect this is a big reason and will be getting bigger as we start seeing more employees who went to school in the AI era.
This is also the real reason managers are so enamored of AI: reading and writing are, to them, the biggest obstacles in a typical day at work. Any machine that can help with this is welcome, and they don't have any experience what precise communication is actually like to understand how poor a replacement it is.
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.
I was involved in one startup in particular where "trust" was important. They didn't understand why I was pushing to build a native Android/iOS app and have it on the app store, as opposed to a PWA.
It's because, like it or not, having an app on the app store makes you look legitimate, it makes you look like a real company.
It was a pain in the ass, a PWA would have been way easier, but I still maintain it was the right call.
Not saying it wasn't right to actually build the app, but you could have sidestepped the issue if that wasn't the priority
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.
If you don't value your developers perspective in the sales cycle, you are fundamentally doing something wrong. Developer's don't necessarily hold more product knowledge than anyone else, but they sure as shit can tell you how your company can make an extra 100k on a sale by just adding 10 more lines of code.
Sales are incentivized to sell, developers are incentivized to provide impact. Include them.
I can say, from experience:
1. Everything gets better the more technical people are involved with customers. Sales, biz dev, tech supp, trade shows, etc. Probably not as the point person, probably not solo, but mosdef involved. And not every tech has the aptitude, or desire, to be customer facing. YMMV. Still, conversations are shorter, more productive. Customers respond very well. It's been a huge win-win, every time.
2. It's always been hard to convince (commission driven) sales people to loop in techs. It's two separate cultures. eg Upon success, sales person gets a new Porsche and the tech gets more work. Which causes resentment. I don't begrudge high rewards for sales (it's a tough gig). But some perks for the grunts would be nice too. Just saying.
"Garageware" is what we called that type of software. Because it truly was, often built using old protocols, outmoded security mindset, etc.
It did the job our staff required (and may have been the only piece of software to do so) but it wasn't our favorite to deal with from a technology perspective.
Our super-lucky big first customer, it probably helped that we spun out of an established small engineering firm that did notable R&D work for huge companies, and also that we partnered with a huge hardware tech company, who had an evangelist who put in a good word for us at times.
And after a successful launch for a prestigious big company, we could point to that, to increase our credibility with other big companies (especially those in the same and similar markets).
For some co-design work leading to pilot we landed (intending to lead to a pilot), we worked together with their in-house product design team, on big brand-involved technology changes to their non-computers-tech advanced products, and also planned out the manufacturing and distribution logistics integration. (I think this one probably would've gotten to a pilot, after some delays, but we'd stretched our runway until it snapped, and there were various reasons we didn't get a bridge and didn't raise.)
For some prospects, we got access to CEOs or other execs, and the message came downwards to work with us. (Which seemed to nevertheless often have people below thinking in the usual CYA ways. But our foot was in the door, and our size had at least a provisional OK. Though some of those devolved into too many stakeholders being roped into meetings, which meant more use cases to be satisfied, including by people who were half-hearted about it, and this probably wasn't on their KPIs.)
Other prospects included smaller companies in some categories (e.g., a founder grew a sustainable business designing and making a high-quality physical luxury product). I think those were probably fine with us being small, and that they liked the direct access and our willingness to work with them and adapt to what they needed. The challenge there might've been finding PMF with a customer who understood every aspect of their company, who feels every dollar, and who didn't get where they are by introducing costs and complexity they weren't sure they had to. (By contrast with large companies as customers, anyone who's had to use some of the products of enterprise SaaS purchases knows that large companies aren't always that discerning in what they spend money on or what complexity they introduce.)
Bigger companies were also easier for one of our sales tactics, because their products had the popularity and volume to show up significantly in some bespoke data acquisition stuff from osint that we developed, which we used to prepare reports for cold call prospects that showed a money-losing problem they had, which maybe they didn't know about.
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.
Working in healthcare (electronic medical records), that was a standard line item for our customers.
Good thing too; after acquisition, our grandparent company's execs quickly found a new leprechaun to chase after, and our product died on the vine. Despite first mover advantage, great revenue, and pipeline of prospects, our tiny effort was less than a round off error to the grandparent (Quest Diagnostics).
It means that my client can always get a contractor in at some later stage to modify the system to their hearts content.
You’re a little company, now act like one https://news.ycombinator.com/item?id=1395164 (June 1, 2010 — 153 points, 14 comments)
You're a little company, now act like one https://news.ycombinator.com/item?id=795976 (August 31, 2009 — 240 points, 53 comments)
At least for myself, I've only experienced shock/surprise when people find out the size of my company (1), this normally happens either never or late/after the sale. I'm sure the software-buying process in an org is always a challenge, but my product replaces a in-person-only/physical-only workflow so there are, understandably, some people who are nervous/apprehensive about the change to software. Injecting any extra uncertainty based on company size/sales into process seems unwise.
I _never_ lie but I also don't start the sales pitch with "Hi, I'm a 1-person company with X previous sales".
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