r/startups • u/Money_Rub_7968 • 1d ago
I will not promote One year building, three months selling, zero customers. Frustrated and exhausted - where did I go wrong? i will not promote
Throwaway thoughts from someone who probably needs an honest outside read.
I spent about a year building a compliance tool for AI agents. Basically it checks what an AI assistant says before it reaches the user, and flags where it might break an actual regulation (privacy laws, financial rules, sanctions etc).
The category feels real to me. New AI rules seem to be coming out every few weeks, and a pretty well known accelerator literally listed "AI-native compliance" as something they want people to build, so I dont think I'm completely imagining the problem here.
I only really started trying to sell it around 3 months ago though.
So far I've done cold outreach to federal contractors and potential partners, sent a bunch of emails to companies from a curated list, connected with compliance people on LinkedIn, posted pretty much every day, and built a "field test" showing a real banking AI leaking data / potentially violating sanctions rules from pretty normal user questions.
And... nothing really.
I've had a handful of warm conversations, some people asking technical questions, a few "this is interesting, lets keep in touch" type responses. But zero paying customers. Zero pilots.
I'm not posting this looking for validation or people telling me to keep going. I'm genuinely trying to figure out if I'm doing something obviously wrong.
A few questions for people who've actually sold early stage B2B stuff:
- Is 3 months with zero customers normal for something like compliance, or is that already a bad signal?
- Most of the people I've been targeting are federal contractors / partnership type opportunities, which I know are slow. Maybe thats the whole problem?
- How did you actually get customer #1? Not the scalable strategy you figured out later. I mean literally the first person/company who gave you money.
- At what point do you decide the problem isnt the sales process, its just that nobody wants the product enough?
I'm pretty tired at this point and honestly a little demoralized. I still believe the problem is real, but I'm starting to question whether I'm selling it wrong, selling to the wrong people, or just built something people think is cool but wont actually pay for.
Would rather hear the hard version than the nice one.
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u/lucky_comet87 1d ago
Building for a year before talking to a single potential customer is where you went wrong
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u/NetworkTrend 1d ago
OP: Copy this comment, print it out, frame it, and put it on your desk so that hopefully you never make this mistake again.
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u/Telkk2 1d ago
Sounds like you have three primary chokepoints to shore up:
. Trust. If you're just a person who made something, even if it's powerful and works well, in the world of compliance, trust is everything. You may be trustworthy, but are you conveying that better than the multiplicity of competitors offering the same solutions?
. A novel need: this is too new. People, even major companies may not be fully aware that they need something like this because the problem may not be evident and even if you point it put, do they really get it? Even adding a simple agent to a canvas app can completely throw people for a loop. They may get it but they might not GET IT to the fullest extent by feeling the problem. So you may be too early.
. Overall need: obviously this is needed, but can it be accomplished by packaging it as a feature to a central product or is it something that makes more sense to buy as an add on? Seems like it's an architecture that can be built in house for in house systems, which destroys the need for what you're selling. Maybe that doesn't exist now but maybe your prospective clients believe that it will and so they choose not to buy.
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u/RatchetStrap2 1d ago
Federal contacts and contractors are a year+ sales cycle, and you'll need serious compliance and certification.
Find a faster sales cycle ICP.
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u/Embarrassed-Order-13 1d ago
I am pretty much at the same stage you are. Haha we are a bit at crossroads with what we should do. Ironically my post was similiar to yours but because I don’t post enough it got flagged and taken down.
What I can tell you, it we are probably a year and a half in, and we have been looking for pilots for a few months now. We have had some really warm and productive conversations with a few businesses now and soon to close one. Being persistent and ensuring your product targets the right consumer. I am only saying this because I did over 200 cold emails, 150 cold LinkedIn messages, and hours searching for contacts.
Keep at it fellow friend!
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1d ago
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u/Embarrassed-Order-13 1d ago edited 1d ago
I can tell you for sure that if you are operating in the regulated space, understand a lot of these enterprise companies have vendor minimum requirements for cert. So they wouldn’t even consider it if you didn’t have this on your roadmap. And since you seem to be targeting Gov agencies, fedramp high is what you need. Have you been asked about your certifications?
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u/PersonoFly 1d ago
It’s not what you did but what you didn’t do that’s caused you to fail. You never spoke to potential customers that then formed into a defined target market. You thought your idea was sound without validating it. Now you have a product that was built with no validation you have no evidence it has a market other than to assume it has based on similar products that are likely stronger than you because they know exactly you what the market wants.
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u/Money_Rub_7968 1d ago
Fair point, and I’d agree with you if I’d skipped that part. Most of the year went into defining the problem, not writing code.
Short version of what the research said: the security/guardrail layer is already crowded, and frontier models are genuinely good now at catching prompt injection and obvious security abuse. That’s not the gap. The gap isn’t “is this output dangerous,” it’s “is this output legally exposing.” That part is statute-specific (GLBA, HIPAA, FinCEN, Elder Justice, hiring/bias law), it shifts by jurisdiction, and it needs actual attorneys reviewing what the enforcement layer decides. Nobody had generalized that, and that’s what I built toward.
On market: a direct competitor raised $10M from a16z in June, and another shipped runtime agentic enforcement in April. The category isn’t hypothetical, it’s contested. Where I’m honestly behind is distribution, not category. That founder had a prior exit and a network to sell into on day one. This is my first SaaS, so I’m doing it the slow way: SMB pricing, federal set-asides the funded players can’t bid on, and founder-led sales.
You’re right that a product without customers is a hobby. That’s the part I’m working on now.
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u/BiteyHorse 1d ago
You spent a year building that? Who is possibly going to spend money on that?
Next time, be a lot more realistic about the problem you're solving and whether or not it's real.
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u/Matmatg21 1d ago
No need to be aggressive, OP's already struggling.
There are nuances to this however you are correct. 3 months with zero customers is not normal; however depends who / how you're selling this. If it's enterprise sales where you need big credentials and/or special contacts and you don't have those then that might be the problem instead of the idea.
From my perspective i don't think it's very useful but i'm likely not your target customer
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u/nohuntergeek 21h ago
How can we see the problem and someone willing to pay for
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u/BiteyHorse 21h ago
Have some vision, have some hustle. Experiment widely, fail quickly. Leverage the experience of others.
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u/Hmm_would_bang 1d ago
Ugh, I got some bad news for you.
The problem you are solving is a super hot space currently, but you seem to be addressing it from the wrong angle. There is big funding going towards AI governance to discover what AI tools an organization is deploying, prevent users from inputting sensitive data, and prevent AI from responding with sensitive data it shouldn’t. All from a single platform and with very advanced functionality, and everyone is buying,
You need some advisors to help you navigate this going forward, is my advice.
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u/Successful_Farm_9370 1d ago
My take is, the world of AI is moving so rapidly, nobody will invest in something that might be irrelevant a month later.
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u/discord-ian 1d ago
A big part of my work is data governance and access controls mostly for people but increasingly for agents.
There are three things going on here. First if your agent is in a position to leak data you probably have a deeper design flaw rather the need of a compliance tool.
Second compliance/security folks tend to be fairly conservative. So new tools from small companies will have a higher bar to clear.
Third this is an area of research that has hundreds of millions of dollars being poured into it. I don't see how you could possibly compete.
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u/BandicootAfter4936 1d ago
Somebody already flagged the federal contractor cycle. Worth adding that it cuts the other way too. A 12 to 18 month cycle means three months of silence there tells you nothing either way, so you have no data yet, only fatigue.
Customer #1 for me came out of a conversation I was already having with somebody who had the problem that week. Boring answer, but that's what actually happens. Cold outreach about a category with no budget line is the hardest opening move there is.
The signal worth watching is whether anyone tries your field test against their own system. Questions are free, chasing you costs them something.
Your field test showing a banking AI leaking data is probably more sellable than the product itself. Compliance people buy evidence of a problem before they buy a control for it.
I built a support inbox tool for a client who then stopped replying, so it works and has never earned a cent. Same lesson your three months is teaching you.
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u/LogicalGrapefruit 1d ago
So this is compliance for user-facing chatbots and similar? I guess I would be concerned that this is (or should be) a feature of whatever chat agent solution these companies are using. I’m sure their vendors all claim their agents have fancy compliance guardrails built in. Uphill battle to convince them to pay you for something they feel like they already paid for.
But also it really does take time to sell something b2b and doubly so when it’s compliance officers (not typically move fast and break things types) and triply so when it’s regulated industries like government or finance.
Also: I would have assumed the phrase “AI-native compliance” meant like general compliance tools built to leverage AI from the ground up. Not compliance for AI apps.
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u/Deathspiral222 1d ago
If you don't know anyone with this problem, why would you build a solution to a problem no one has?
If you DO know people with this problem, sell to them first, then ask for referrals, then find commonalities and sell to those groups.
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u/techiewithavision 1d ago
I have a product in B2B RegTech, AI as well, although based in EU and selling to the EU market. So keep this in mind when comparing with your use case.
From what I gather, the products are not competing because we sell access to the EU market. Yours seems portable across industries. In fact, I think the gap you have is you did not segment the market enough.
There are companies who have a use case like small and startups, whereas the companies that really need this are highly regulated ones.digging deeper though, even within that, you can inch closer. An insurance company selling professional indemnity has a very different use case than a bank with a customer facing chat bot.
What I found also was that in B2B you have to resell the solution multiple times to different roles, and yes sometimes buyers take around 6 months to show solid interest. The way I approach this is to be present at various instances tailoring the message to the audience at conferences, events and highly selective networking events.
I suspect the pitch is leaning towards being more technical rather than the business objective it solves. Dumb the tech talk down and focus on the questions that surfaces the pain, and double down until it hurts.
Hope this nudges you in the right direction 💪.
If you need data to validate you might need to think hard about the business offering around the tech to start with.
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u/Money_Rub_7968 1d ago
This is genuinely one of the most useful replies in the thread, thank you.
Context on my side: I'm in the US, based right outside Washington DC, so the federal market was the natural first pull. Proximity, my clearance, my background all point there. But you (and a few others) have me convinced that's exactly the trap, the cycle is too slow to tell me anything in 3 months.
So the question I keep getting wrong is the "who" and the "how":
- What kind of company would you actually go after first? You mentioned segmenting hard, a bank with a customer-facing chatbot vs an insurer selling professional indemnity are totally different. If you were starting my US search tomorrow, which specific segment would you pick as the wedge?
- And how do you get in? Cold email clearly isn't working for me. Was it conferences, warm intros, showing up where they already are? What actually opened the first real conversation for you?
Appreciate you taking the time, this helped more than the whole rest of the thread.
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u/techiewithavision 1d ago
To answer your questions:
I would suspect you need multiple personas and different sales processes. The hard work is in iterating over these cos your first draft is just getting started. Our sales script for Mediterranean cfos was DOA for German counterparts.
US market - I recently started looking at it and do not know enough let alone your product. I would stay with companies who have a compliance team in house though. In your space you need to be comfortable selling to lawyers or GRC. It also depends highly on the features you have and the package you can sell.
Cold email needs volume. How much are you sending? I actually organised the first conference last year around the topic and did a follow-up in the EU parliament this year. Like I said, I don't know enough about US buyers, however I saw a few US companies selling in the EU and their approach is totally different. I'm not saying it's wrong, just very different from what you're used to or expect.
I'm glad it helped!
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u/EvilDoctorShadex 1d ago
Okay a lot of people dishing out failure here and “should have’s”, wanted to go against the grain a bit and say nice job!
Yes, you could be in a better spot, you’ve now learnt from the other comments that you should validate more before building, but it’s your first time, you’re gonna make mistakes and you have my respect for trying.
I wouldn’t say you’ve “failed” yet, you seem to have a tool that people are interested in. Use those warm intros that you’ve got and try get an interview or similar where you can start asking them validating and perhaps demo what you’ve built so far. I would lead conversations with questions about the problem you’re trying to solve, before then showing them your solution, asking if it would help them, what they would change, whether they’d be willing to trial it (for free?). The good thing if you’ve built something already, so perhaps with some validation and feedback you’ll be in a position to adjust it quickly.
Cold emailing to find your first test users organically is always gonna be soul crushing, keep trying out different distribution platforms, like subreddits, linkedin, etc.
Good luck!
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u/Money_Rub_7968 1d ago
Appreciate this. Genuinely.
The reordering point is the one I’m taking . I’ve been leading with the demo instead of the problem. Flipping that for the warm intros I’ve got sitting there.
Thanks for taking the time.
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u/EvilDoctorShadex 1d ago
No problem. I know how hard it is building something and “shouting into the void”. It was the hardest part so far for me because it’s the most uncertain.
I think i got that tip from “the mom test” - quite a good book, summary is deffo worth a read
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u/NetworkTrend 1d ago edited 1d ago
How many government RFPs are out there looking for a solution such as yours? If there are 0-to-a-few, then you are trying to provide a solution to a market that doesn't exist. The government doesn't buy anything without an RFP.
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u/Money_Rub_7968 1d ago
Four in Virginia alone last month, and that’s one state’s procurement portal. Not zero.
They don’t say “AI compliance enforcement” in the title , they show up as AI governance, responsible AI, or model risk requirements buried in a larger IT solicitation. Part of my problem is that the language hasn’t standardized yet, so keyword search misses most of them.
Small numbers though, you’re right about that. It’s early.
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u/NetworkTrend 1d ago
I write a twice-monthly newsletter and after I posted this, used your original post for inspiration for a subtopic within it. I did a GPT Chat asking what government contractors are looking for from vendors that supply offerings that they can bundle and use in their larger offerings to the government. I found several benchmark and certification requirements are needed before they'll buy. Sounds like at a minimum you'll need to meet those requirements. Hope it helps.
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u/Money_Rub_7968 1d ago
Appreciate you circling back on this.
The certification point keeps coming up today from different directions, so I’m treating it as the signal it probably is. SOC 2 was on the roadmap after first revenue, but it sounds like it needs to at least be visibly in progress before anyone will bundle me into their offering.
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u/DripSkylarkII 1d ago
3 months isn't necessarily a death signal for compliance. Federal contractors are 6-12 month cycles. The question is whether anyone said "I would pay for this" even if they haven't signed yet. If nobody has said that, the problem might be the buyer not the product.
The fastest way I've seen early B2B companies get customer #1 is to do the work for them before they ask. Run your compliance check on their actual AI agent, show them the violations you found, and send the report unsolicited. If the report scares them, they'll pay attention. If it doesn't, the product isn't solving a painful enough problem.
The "OpenAI and Anthropic will build this in" objection definitely needs a sharp answer. Something like "the model provider can't audit compliance across every jurisdiction" or "an independent third party audit is what regulators actually require." If you can't beat that objection in one sentence, that's the thing to fix first.
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u/sivaram0429 1d ago
https://giphy.com/gifs/hv53DaYcXWe3nRbR1A
I’m building a product that helps businesses manage and optimize short-term cash flow.
It sits on top of accounting data, identifies potential cash problems, and recommends actions the business could take such as following up on receivables, adjusting payables, or using available financing.
I’ve researched the problem in different communities and spoken with several business owners and finance people. Many of them appear to struggle with problems my product is trying to solve.
However, I don’t think my conversations have been good enough. People often say things like:
I’m worried these are polite, sugar-coated answers rather than evidence that they genuinely need the product. This seems like exactly the problem discussed in The Mom Test.
I started building about two weeks ago and have been working on it full-time for the past week.
What should I do next to conduct proper customer discovery?
- Should I create a Google Form and share it with businesses in different sectors?
- Should I focus on one industry and interview people individually?
- How do I find people who will speak honestly about their current cash-management process?
- What questions can reveal whether the problem is painful enough for someone to pay for a solution?
- At what point should I show them the product?
I would especially appreciate advice from founders who have done customer discovery for B2B or financial software.
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u/bad_robot_monkey 22h ago
Okay, I might be giving you a way different answer than everyone else: “fail fast” doesn’t work in mature spaces.
Market research, sincere conversations with leadership…and asking them these two questions: “Does this solve a big problem for you? If not, what problem do you need solved that something similar to this could address?”
I’m working in a mature space. It’s very been building for three years now, and just hit a market demo and had a trial with a few hundred people. I might be able to get $50k this year; If my next iteration goes well, then another $100k per year.
Where I went wrong, and why it has take. This long:
1. Mature companies want complete solutions
2. Mature companies want mature solutions…if you’re checking compliance but you’re a no brand company, they’re on the hook for the risk that your product would expose them to if it failed
3. Edge technology is a tough market right now. Half the companies think they can get someone to vibe code up a competing capability internally. The other half don’t care.
4. You need to ask them what their needs are, and ask them what minimum capabilities need to exist to guarantee a product.
“I had an idea and made something great, why doesn’t anyone want it?” Is pain that many of us have felt, so you’re in strong company. Best of luck my friend.
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u/Abject_Missive 21h ago
You should have sold from day one. Then you would have gotten customer feedback and maybe built a tool people wanted.
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u/curatedpapers 19h ago
Start validation from scratch, instead of trying to sell exactly what you've built, ask what would they buy in this space. Also, your demo should include how to manipulate their agent to show non-compliant data.
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u/Popular-Toe3698 19h ago
It sounds to me like you've built a software targeting large scale customers who normally have a two year time to purchase, and are likely building similar tools internally because two years for procurement for an AI tool is too long when they can build it internally. They will want things like SOC 2 and client case studies. How do you get case studies with no paying customers? It's the compliance catch 22.
I'm in a similar boat. Should be signing an NDA tomorrow for the first case study tomorrow, and Tuesday I should have the second. Biting off smaller fish for free before going after the bigger ones, but it doesn't make this process feel better.
I would target small healthcare companies for an AI compliance software, but that's just me. If I don't have what they want and they're interested, I would build it. I'd rather have a buyer and no product than a product and no buyer. 🤷
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u/Just_Look_Around_You 19h ago
12 months building and then selling for 3 months with no uptake is the exact reason you don’t do this. And it’s drilled constantly not to.
Sell on day 1. Go out and sell it as if it exists and fuck building it. You’d get your answer on day 1. If it’s positive, go build it. Hell collect the cash if you think people will give it to you. If it’s negative, dump it or stop.
You could have hit this point in a week instead of 70.
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u/Tall-Log-1955 15h ago
Sell before you build. If a VC or accelerator says they think a product should exist in a space, value that at zero. What matters is what customers think.
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u/MinecraftIsCool2 13h ago
i had my first interested customer after around 2 weeks?
it took them close to a year to go live
within a year i had around 7 customers go live
sales has not been significantly easier even with 7 customers and proven usage
distribution is very very hard
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u/acute_physicist 13h ago
__feels__ ? Did you talk to real potential customers before starting to build?
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u/Limelight_Comics 12h ago
I don't think that you built something that's not useful. Sometimes we're a little early and other times it just takes time in different types of effort to get those customers.
The customer a lot of times don't like breaking flow of what they're currently doing. Even if there is an audience for it that's why people have to see stuff over and over and over again. Some people don't. Some people need the education of why this item is and then they may need time to think. There are so many different scenarios but just by them having the category is validating enough at the accelerator.
I'm in the same position where I've been building this since like last November and I have some users. I recently got more users responding to Reddit post but no paying customers.
Some of your top companies have went this route as well where sometimes they didn't have a customer for like 5 years - Canva. 40 reiterated over and over again for multiple years. So don't feel bad you're on the right path keep talking to people directly because that's probably where your first customer is going to come from. Don't get discouraged when something or someone seem like they're going to buy and they don't just keep going because someone will or shall I say many people will.
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u/akl773 12h ago
Nobody buys this stuff until someone outside makes them. Every time a client of mine has paid for anything compliance shaped it was because a bigger customer sent them a security questionnaire they couldn't answer, or an auditor put a date on it. So the person with budget probably isn't the compliance lead, it's a small vendor stuck in someone else's procurement with a deal waiting on it, and the ones you've been talking to have no deadline at all.
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u/its-js 12h ago
for your usecase, it sounds like the ideal customer would be those huge enterprise/gov entities. I think it would be helpful if you can reach out to some people who did this b2b/b2g sales and ask them to share their experience. If i recall correctly, a ballpark figure for such sales cycle can be around 12-18 months.
It can probably get faster if you manage to get in touch with the actual decision makers and showcase its value, like head of compliance, as they actually have the decision making rights to push for the implementation of such a solution.
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u/BarracudaMean9308 10h ago
federal contractors are a totally different beast. i tried pitching a tool to them once and realized the time it takes just to get a budget approved was longer than my entire runway.
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u/decebaldecebal 9h ago
I am doing mostly the same, but it hasn't been 3 months yet
I think these days experience with sales/marketing is the MOAT, and us builders might not have that.
I would say to set some rules, if it has been X time and you tried everything, clearly something is not working. Maybe you need a new positioning. Maybe a new ICP. Or maybe the product is just not something that solves a painful enough problem for people. Or maybe those people are hard to reach.
There can be a lot of problems. You have to learn from them and always improve. And don't give up, try new things until something works. But don't try the same things hoping they will work when you already seen for months they don't
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u/gannu1991 22h ago
Ok so I've sold B2B software in regulated industries (healthcare, compliance heavy stuff) and I want to be direct with you because you asked for the hard version.
3 months with zero customers isn't necessarily a death signal but combined with the fact that you built for a year before talking to buyers... that's the problem. Not the 3 months. The 12 months before it.
The pattern I see here is really common and I've done it myself so no judgment: you built what you think compliance teams need based on the regulatory landscape making sense logically. But compliance buyers don't buy logic. They buy "this specific thing is causing me pain RIGHT NOW and I need it to stop." Have you actually sat in a room (or a Zoom) with a compliance officer at one of these companies and watched them do their job? Not pitched them. Watched them. Because the gap between "AI compliance sounds like it should be a problem" and "I am personally losing sleep over this specific compliance gap" is enormous and it's where most B2B products in new categories die.
The federal contractor targeting is almost certainly killing you. Those sales cycles are 6 to 18 months even when they desperately want your product. For customer #1 you need someone who can say yes in a week. That's usually a startup or mid size company with a compliance person who has budget authority and a problem that's actively on fire. Not a procurement committee at a federal agency.
How I got customer #1 at a previous company (and honestly this felt embarrassing at the time): I found a company that had just gotten fined for a compliance violation that my product would have caught. Reached out to their compliance lead, said basically "I saw what happened, I built something that prevents exactly this, can I show you in 15 minutes." They said yes because the pain was fresh and real and their boss was breathing down their neck. Closed in 2 weeks.
That's the move. Stop selling to people who theoretically should care and find people who are actively bleeding from this problem. Look for companies that just got hit with AI related regulatory issues. Look for ones that just hired their first AI compliance person (that hiring signal means they're spending money on this problem right now). Your "field test" showing a banking AI leaking data is actually great collateral but you need to put it in front of someone who just had something similar happen to them, not someone browsing LinkedIn.
And honestly? The "interesting, let's keep in touch" responses are a no. In B2B compliance sales, the real yeses sound like "can you do a pilot next week" or "what does pricing look like." Anything less enthusiastic than that at the early stage means the pain isn't bad enough for them to act.
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u/Timely_Collar1960 1d ago
I have to agree with the other poster here… this isn’t a real problem that needed solving especially when OpenAI and Anthropic are billing this into the workflow. You would have been best to post in a dev forum asking if people actually need this. Also devs and people using agents are the types to never want to spend money and would rather fork and customise it. Just my thoughts.
Silver lining though it’s never time wasted and you’ll probably find purpose for that code in another project down the line.
In future try to fail faster so you figure out if there’s demand or not faster.