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).
ivape · 3h 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 · 3h 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 · 5m 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
eszed · 3h 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.
fuzzzerd · 56m 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 · 36m ago
What services do you offer, exactly?
myflash13 · 5h 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”.
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 · 7h 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 · 7h 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.
SoftTalker · 6h 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.
dmd · 6h ago
Counterpoint: If I had to talk on the phone with the company instead of using text, I would choose a different company.
collingreen · 6h 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 · 5h 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)
3dsnano · 7h ago
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
ensignavenger · 7h ago
Personally, I like hyphens, a lot. I don't understand the trend of removing them. But whatever.
layer8 · 6h 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!
pesfandiar · 4h ago
Perhaps it looks less AI generated without perfect punctuation.
cut3 · 7h ago
I do as well which is why im trying something new in a new project. Hard to start but im getting there
moron4hire · 7h ago
Missed opportunity to say that you're a hyphen-enjoyer.
ensignavenger · 4h 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 · 7h ago
Understanding-absent of the removing-them trend.
w10-1 · 3h 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?
danenania · 7h 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 · 7h 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.
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 · 5h 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.
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.
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.
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.
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)
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?
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.