I would've liked to hand articles like this to someone, when I was making related arguments about not pretending to be a big company.
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).
frr149 · 45d ago
I'm experience, that doesn't work if you main clients are big corporations. The average corporate drone mistrusts and disregards small companies. Not out of arrogance, I believe, but out of fear: a generalized version of the old "no one was fired for buying IBM" trope. Small companies are seen as higher risk.
DougN7 · 45d ago
Yes, I agree. I was honest with a large customer about how small we were and although _he_ was willing to take a chance on us, he said we absolutely needed look bigger to gain other customers.
p_ing · 45d ago
> The average corporate drone mistrusts and disregards small companies.
"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.
Gravityloss · 44d ago
In many markets, there are different kinds of customers. If you're the innovative upstart, you perhaps attract more innovative and open-minded customers as well. From there, when you've delivered value, it's then quite a lot easier to work with the more conservative ones.
sanderjd · 45d ago
I mean, small companies are higher risk. When you're small, is it better to find customers who are explicitly accepting the real degree of risk, or customers who are underestimating it because of how you presented yourselves to them?
neilv · 45d ago
Agreed, but being a small company can still work for some big-company customers, depending on how you approach it, and mostly how lucky you are.
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.
ivape · 45d ago
What are the incentives for sales for allowing you to do that? What incentives do people in agile or product development or management have to let developers partake? There's nothing to gain and everything to lose. See, I would love to live in Disneyworld too.
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.
neilv · 45d ago
In an early startup, there shouldn't be fiefdoms nor (intra-company) empire building.
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.
mystified5016 · 45d ago
Anecdotally this rings true. I'm currently watching a CEO destroy their startup by trying to build an empire in a team of 15, while everyone else just wants to make the company work together. No investor ever speaks to staff, nobody but CEO is ever allowed to pitch, or even be present at a pitch. All cofounders and most staff have quit because it's so ridiculous to try and rule over such a small team
recursivegirth · 45d ago
Understanding this isn't necessarily my audience, I am not a startup, instead a freelance consultant. I could call it a startup, but that would be stretch, and I am not interested in VC funding.
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.
specialist · 45d ago
I honestly can't answer your questions.
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.
gnuser · 44d ago
When you've been saving the entire company on the reg and get a 1k Christmas bonus and the sales guy gets your entire salary as a bonus, yeah, it causes some fucking resentment!
eszed · 45d ago
My company is medium size, at least within our industry, and I actively look for little companies. Every complex platform has bugs and un-considered edge-cases and poorly thought out engineering choices. Large companies don't fix them; small companies do. (That's overstated, obviously, but not wildly so.)
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.
specialist · 45d ago
Have you ever negotiated having the source code (etc) put into escrow, should the vendor abandon the product?
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).
lelanthran · 44d ago
I'm technically a small company (solo consultant) but I always offer the sources as a non redistributable irrevocable license.
It means that my client can always get a contractor in at some later stage to modify the system to their hearts content.
fuzzzerd · 45d ago
Sounds like you are had some experience that might leave you with some unique insights into markets underserved by small players that can deliver continuous improvements.
isaachinman · 45d ago
What services do you offer, exactly?
latchkey · 45d ago
Small companies are hungry.
myflash13 · 45d ago
There are exceptions. For example in fintech or anything in finance that requires trust, you want to seem bigger than you are. In contrast to OP, I’ve lost customers in the early days when they found out I was a solo founder. It’s more “normal” to share your financial data with huge companies who don’t care about you, but it’s scary to give it to “some guy”.
jmkni · 45d ago
This is a good point.
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.
joseda-hg · 43d ago
I mean, if you only wanted it for credibility, couldn't you just wrap the PWA and publish it to the playstore?
Not saying it wasn't right to actually build the app, but you could have sidestepped the issue if that wasn't the priority
danenania · 46d ago
Great post.
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.
ednite · 46d ago
I agree with your comment and couldn’t agree more with this article. It’s solid advice for anyone just starting out with a product or service.
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.
I don't find it paywalled, but here is an archived version for you to read: https://archive.is/e4O1W
locallost · 45d ago
Heh, I'm kind of in the same or similar boat. I changed jobs specifically last year to join a smaller company, thinking we'll get a lot done without a lot of fuss and stakeholders, which was bothering me in my previous job -- it was impossible to get something going. But it turned out my new small team spends a lot of time trying to do the work of 50 people with 1/10th the resources, essentially cosplaying a large brand. I said we're not X, we're Y, and let's be that because it has its advantages, but people are busy with case studies, UX, patterns etc. The funniest part is they are laser focused on a competitor and a lot of the talk ends up being "do it like competitor X does".
So yeah, you're a little company, act like one.
ryandrake · 45d ago
I worked at a medium sized company attacking a market dominated by one or two gigantic FAANGs and it was really sad how focused our leadership was on copying them feature-for-feature and watching them closely to do whatever they were doing. Surprisingly, they also had far more process and red tape in place slowing down routine things than I encountered in BigTech. They were always agonizing over easy product decisions, and second guessing themselves and waiting to see what FAANG does when they should have been taking risks and differentiating themselves. Like, come on, guys, use our few advantages over them and do something great and unexpected!
Nope, it was always stuff like: we need to do another grand redesign because we want to change our brand look and feel again.
Being small is a unique selling point. Lately, I was talking to a small business owner who runs his business over Whatsapp. He was interested in creating some kind of customer portal.
I advised him against it. No digital concept is going to beat that customer experience.
AaronAPU · 46d ago
One of the best decisions I made as a solo founder was putting a note on product pages to contact me to request a loyalty discount for existing customers.
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.
mnahkies · 46d ago
I've been a bit of a skeptic around that, but recently had an amazing experience with a small motorcycle rental company where we arranged everything over Whatsapp.
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.
csomar · 45d ago
You'd be surprised but in SEA for 1-4 persons small businesses, that's how you do business. There is no website, offers are sent as pictures. Whatsapp is also used for everything else. I had one rental take a photo of the deposit and sending me the picture.
aitchnyu · 44d ago
I'm Indian and see simple websites can get complicated quickly and nobody can edit a phone number without renewing the contract. So Whatsapp and pictures are the internet enabled stack of choice. Also there is so much lying and repudiation of lies that pics over Whatsapp are the "written statement". Traffic police take photos of haphazardly parked cars, makers share photos of in-progress works etc.
SoftTalker · 45d ago
At that point I would prefer a phone call. And I don't like unnecessasry phone calls, but protracted discussions over chat is awful.
drewcoo · 45d ago
A text record of what happened isn't just useful for new hires, not just useful for async comms, but for people like me who want to be sure we followed along.
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.]
ElevenLathe · 42d ago
> [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.
dmd · 45d ago
Counterpoint: If I had to talk on the phone with the company instead of using text, I would choose a different company.
const_cast · 44d ago
Text accomplishes the same thing but spread out over many hours instead of, like, 5 minutes. Phone call + summary email is so much more efficient.
lostlogin · 44d ago
You prefer the AI slop that pours out?
collingreen · 45d ago
I see where you're coming from but a text record you can go back and review is very valuable to me in these situations as well.
mnahkies · 45d ago
Phone call was available, but I choose chat in this instance. It wasn't a particularly complex conversation - I outlined my experience, and my doubts from my research and he came back with availability and some direction. I was on holiday with family in a different part of the country whilst arranging it, a few weeks out so there was no real time pressure. Tbh I'm also somewhat adverse to phone calls for no good reason.
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)
const_cast · 44d ago
Customer experience is great, but technology can be part of customer experience. For something like a private practice, allowing patients to access test results or medication information outside of working hours is a huge boon. Not to mention the time you can save on your phone line if patients self-schedule.
ensignavenger · 46d ago
Personally, I like hyphens, a lot. I don't understand the trend of removing them. But whatever.
layer8 · 45d ago
Me too, as they improve readability when used correctly. They are there for a reason. In the quote in the article, the hyphens in “risk-analysis” and “decision-support” are incorrect, however. Know your hyphens!
f30e3dfed1c9 · 45d ago
I've been complaining that nobody knows how to use hyphens anymore for ten or fifteen years. I used to send a friend examples from pretty big, well-known publications like Time magazine, the Wall Street Journal, and others. I've given up hope and accepted that this is just the way things are now.
pesfandiar · 45d ago
Perhaps it looks less AI generated without perfect punctuation.
moron4hire · 46d ago
Missed opportunity to say that you're a hyphen-enjoyer.
ensignavenger · 45d ago
You know, I re-read my comment before submitting it, and one thing I thout was- I'm not using enough hyphens in this comment! But alas I submitted it anyway.
OJFord · 46d ago
Understanding-absent of the removing-them trend.
cut3 · 46d ago
I do as well which is why im trying something new in a new project. Hard to start but im getting there
joshstrange · 44d ago
I think this advice is very dependent on the situation. There are many cases where you will not even get your foot in the door if you advertise the true team/company size.
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".
vulnerability can be a superpower if leveraged correctly… i think it leads towards more authentic conversations and weeds out the folks who don’t “get it” yet
w10-1 · 45d ago
This 2009 advice to be accessible when small is highly relevant for the many outside work who haven’t managed to catch the AI wave, or for those AI companies targeting micro-niche.
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?
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).
"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.
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.
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.
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
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 advised him against it. No digital concept is going to beat that customer experience.
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.
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.
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.
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)
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".
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)
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?
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