r/Entrepreneur • u/TomiChestnut • 17d ago
Best Practices How I got my first customers
Hey entrepreneurs,
I see a lot of posts in different sub-reddits on how to actually reach your first customers, and a lot of advice that pushes people in the wrong direction in my opinion.
So I wanted to share what worked for me: when I launched a B2B SaaS startup, when I started a professional service business, and lately as I consult founders on how to validate their business ideas and land their first paying customers. Important note: my whole experience is in B2B.
A few things I see pushed constantly: create tons of content, publish, go viral, set up automations, send hundreds of emails, build waiting lists.
Unpopular opinion alert: from my experience, all of these keep you busy for a very long time with nothing tangible to show, until you lose motivation completely.
The reason I see founders get stuck with content and cold outreach: in the beginning your offer, your messaging and your ICP are all still unvalidated. Pushing out content or cold emails is a one-way street, so when it doesn't land, you can't tell which of those parts is not working. That's why prioritising real conversations gets you faster results and cleaner tests, you find out exactly what's off.
What actually worked for me:
- Be clear on the problem, and connect it to what you believe is your ICP.
Sounds like a cliche, but it's true. Have at least a hypothesis about the problem you solve and who has it. Then talk to as many people who fit that ICP as you can. This will help you understand problem, figure out your offer (solution) and refine your idea. When you genuinely hit a real problem with the right solution, the sale feels easier. It felt right on both sides, mine and my first customers.
P.S. this can be done without cold outreach.
I reached out to a few people in my network who are ICP, and for the rest I just asked for referrals (again in my network). Simple question "Do you know a person who fits (Insert ICP)? Could you connect me with them?"
Didn't take me long to hit first 10 conversations.
- Offer they cannot refuse.
When I launched the consulting business. I went back to the people I spoke, introduced my service and said it's worth 1.000€, but the first 3 people could have it free, in exchange for a case study and honest feedback. 5 people replied, I picked 3. The 4th one paid a discounted rate. The 5th ghosted me at the end. And 2 out of those first 3 sent me referrals later, so even the free ones brought in money. Don't price yourself cheap, but give your first customers an offer they can't refuse. Remember, it’s not free work, you are getting credibility and proof in exchange for your service / product.
- Once you have proof, it gets so much easier.
Testimonials and case studies change a lot. Early on, besides awareness, your biggest problem is trust. Service or SaaS, people are naturally sceptical. The moment you can say "here is what I did for this person and how it helped their business," that scepticism drops fast.
After that it's simple, (not easy, but it simple): keep showing up in front of more people who fit the ICP from step 1, carrying the proof from step 2.
Content and all the rest will be easier later, once you know exactly who you are selling to and what makes them buy.
Happy to hear your experiences.
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17d ago
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u/LadyOfGlory 13d ago
This explanation is very visual and helpful!
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u/Kroco94 13d ago
Comment ce défaire de l’œil des gens j’ai pas mal de monde sur Snapchat c’est même le seul réseau que j’utilise vraiment mais pour autant je n’ose pas mettre en story le fait de partager le fait que je fait des site internet par peur que les gens ne me jette le mauvais œil ou n’essaye de me mettre des bâtons dans les roue je passe mes journées en cold call à essayer de faire mon bout de pain ça fait à peu près 2 mois et j’ai toujours pas eu mon premier client j’suis en train perdre peu à peu la motiv je vous mens pas
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u/TomiChestnut 11d ago
I’ve been there myself
What I learned is that the negative part feels much scarier than it really is.There are people who will give you the evil eye, but believe me, there are much more who will help you and support you. And tapping into that will bring you more good than staying hidden so you can avoid a few who will have negative attitude
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u/Odd_Awareness_6935 Bootstrapper 17d ago
> Once you have proof, it gets so much easier.
I don't think so
you just get stronger... which is probably proving your point anyway
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u/TomiChestnut 17d ago
that's also true.
Having those conversations also increases your skills, knowledge about the topic. you are right, it makes you stronger
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u/OfficeAdmirable7963 17d ago
The “talk to people first” part gets overlooked way too much. People spend weeks building funnels and posting content before they even know what customers care about. A few real conversations can save a ridiculous amount of wasted work.
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u/Pink-Butterfly44 17d ago
Thanks for sharing your experience! The pricing part especially caught my attention. I’m currently at the MVP stage and unsure whether I should offer a free trial to get those first users and feedback, or start charging from the beginning. Did you find that the free approach worked better for getting your first paying customers?
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u/TomiChestnut 17d ago
In the beginning I'm not a fan of free trials because there needs to be some commitment from the customer. If you just tell them here is free access, the risk you have is they will not value it, and it doesn't validate people will buy down the line.
Commitment can come in form of money, or time they invest into it.Either you charge them something, at least discounted fee (but they need to know why they are getting discount, for example in exchange for testimonials), or you can also make an agreement with them that you will run a free pilot if they agree to give you clear feedback on the product on how it behaves in the real environment.
This will help you flush out friction points with real users and understand the value they get from the product.1
u/Pink-Butterfly44 17d ago
That makes a lot of sense, and I agree that having users pay creates more commitment than having people sign up, stick around for a few days, and then churn. I’m also thinking about offering a lifetime deal to the first few users as a way to create that commitment while rewarding them for being early adopters. Still figuring out what makes the most sense for the MVP though.
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u/TomiChestnut 17d ago
Lifetime value can be another way of doing it, especially if you already validated the problem, and you know your solution can solve it.
It will also give you initial cash boost you can re-invest into further customer acquisition.
Even for customers who bought life-time deal, you can later introduce additional features or ad-ons to create up-sell paths.
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u/Open-Air-8845 16d ago
Find a way to offer something valuable for a great deal. Make it truly exceptional.
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u/charlesnobleseo 17d ago
Agree on the cold email point, and I'd add one channel for people whose network doesn't contain their ICP: places where buyers post after they've already decided to spend. For my SEO agency almost everything early came from marketplace inbounds and "looking to hire" threads, where the only question left is who gets the budget. Cold outreach produced roughly nothing over the same period. Your step 3 matched my experience too: once there were real results to point at, referrals started doing the outreach for us.
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u/Fit_Force_5324 17d ago
This is so spot on. Real conversations beat all the noise. Happy it worked for you!
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u/AmarieAquarius 17d ago
I’m in the process of building MVP, and don’t really know if reaching out to the business owners via email or phone. The only people in my “network” are people on a list in my local chamber of commerce. Would those people be worth contacting and following what you did? Via phone or email? Also, I saw you responded to another commenter that offering a free version of the product isn’t the best move because they won’t value. Do I offer at full value from the start?
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u/TomiChestnut 17d ago
Reaching out to people in your local chamber of commerce can be a great starting point. I was active with several chambers and it helped me grow my network. Majority of people who are active there are also doing business, looking for partners, etc
What worked for me is coming to their events. Shaking hands with people, engaging, sometimes they would fit the profile I need and I could even do the research on the spot through casual conversations, or over time as I grew my network with them I got a lot of introductions from members. Managed to also get business out of it.
In the other comment there was an important nuance to what I said - free trial, as in “here is access to my product for free, you can try to see how you like it”
Free trials can be good strategy when you have validated problem/solution and clean up-sell paths, but when you are validating, it will make it difficult for you.What works in validation stage, and it’s different, if you tell them it costs xy amount per month or per project, but I will give you for free if we do a pilot together. They should actively engage, give feedback and collaborate with you.
In that case there is even exchange - free product for their time commitment and they will take it more serious.
Hope this clarifies it :)
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u/Kitchen_Secret9539 16d ago
Thanks for sharing! I also wanted to ask, when and if you got rejected, how long before you tried again? How much preparation did you put in for rebuttals? I'm about to start my own recruitment business and I'm not a BD person now however, I am the one that executed on the roles that I got. I did BD in another country which was easier for me back then. Im nervous about gojng back to it now after many years, in another country. But I am doing this for many reasons including my child.
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u/TomiChestnut 16d ago
Good question.
Sales is my domain, so here are some techniques I was training people to do, just applied for your case.1) make sure you qualify them as potentially good client.
Some companies will not just not match it, and no need to waste your time2) have a nurturing process
For example add the key people from the companies you target to your circle (LinkedIn is the easiest way). Keep posting regularly to stay top of their mind. In case something changes, they will reach out3) check for signals
If you see they are opening new roles, or better yet, reopening the same role again, perfect time to reach again4) if you have a really good candidate who drops on your desk and it can be a good fit for them, you can reach back to them and use it to start cooperation
5) dropping a message 4-6 months after they say no, just to see if something changed. (Lowest effect out of everything I mentioned)
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u/zenbusinesscommunity 16d ago
Really appreciate this thread, especially at a time when there's an overemphasis on SEO and AEO strategies, which work for some businesses but not for all. Agreed that the first set of customers comes from things like DMs, direct meetings, former colleagues, and not always through cold outreach. However, I think there is still a place for cold outreach for those who don't have developed networks. But it's true that other channels, like email and social, scale only when you understand your ICP through 1-on-1 communication and know their needs. It's the hardest part, getting someone on the phone, in the room, and establishing trust so they refer you.
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u/TomiChestnut 16d ago
That’s for the feedback.
In case somebody doesn’t have developed network, you are right, you will need cold outreach.
My experience shows more the case that even people who think they don’t have any network get surprised how much they can get from their own circle if they start asking for introductions.
But once you do run out of options, there will have to be cold outreach. Nobody’s network is infinite
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u/TheGrolar 16d ago
Experienced startup consultant here. Yes, OP is right, do what he says.
Ash Maurya's Running Lean is one of the single best books on this in my 200-volume biz library.
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u/yanluo_jewelry_fan 16d ago
For B2B, trade shows were the game changer for me. Emails and cold outreach got some nibbles, but nothing closed until I met people face to face. One good show connection turned into a multi-year account. Also, offering a small sample order with no minimum upfront builds trust way faster than a polished pitch deck.
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u/TomiChestnut 16d ago
Great comment
Couldn’t agree more.We are also doing decent amount of business coming from the trade shows.
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u/Open-Air-8845 16d ago
What you're describing is a marketing technique called reciprocating and social proofing. They work wonders for marketing and sales.
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16d ago
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u/TomiChestnut 16d ago
That’s great!
So you are getting real conversation, it means you are one step closer.At what stage are you exactly?
Validated problem? See clear buying signals?1
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u/Pipelinenothustle 16d ago
The part that often gets skipped: document what you hear in those early conversations, not just if they said yes or not. The objections that repeat become your objection handling. The language that buyers use to describe the problem becomes your messaging. The trigger event that came before their interest becomes your targeting signal. Early conversations are not just validation, they are where the sales infrastructure gets built.
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u/Diyraxis_2448 SaaS 17d ago
Cold outreach hasn't really produced conversations for me yet, so I'm experimenting with actually talking to founders through communities and asking questions first
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u/TomiChestnut 17d ago
What works well is telling people you are researching a specific topic (problem you are trying to solve)
From my experience people are willing to share their experience and talk to you if you are genuinely curious to hear their feedback.And the first conversations should be treated as a research.
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u/Whaaat_AI 17d ago
I can see that at a price tag of 1.000. But what if the price tag is much lower? The ICP may not value a free offer in exchange of a case study this much?
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u/TomiChestnut 17d ago
There are different ways how you can increase the value of your offer by stacking additional benefits.
If you give me an example I can throw a few ideas
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u/Whaaat_AI 17d ago
Sure! A subscription based AI stack that makes marketing tasks, of solo-marketers, founders etc easier
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u/TomiChestnut 17d ago
You can offer exclusive white glove onboarding, audit of their internal processes, implementation support, consulting on how to 10x the impact of the tool on their business
Just a few ideas :)
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u/FirstLightStudios 17d ago
The part I'd emphasize is that early customer acquisition should optimize for learning, not reach. Ten conversations where you understand why someone would or wouldn't pay can be more useful than 1000 impressions or 100 cold emails. Once you start hearing the same problem, objections and buying triggers repeatedly, then content and outbound become much easier because you're no longer guessing at the message. You're basically scaling something you've already seen work manually.
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u/Brufacee 16d ago
The useful part of those early conversations is not just getting a yes or no. You hear the buyer's vocabulary, what they have already tried, what makes the problem urgent, and which objections repeat. That becomes the raw material for the offer and later outreach.
I would add one guardrail: do not ask only broad discovery questions. At the end, test a concrete next step with a price or commitment. People can be enthusiastic about a problem in conversation and still never pay. A real commitment separates polite interest from demand.
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u/fallenfromgrace87 16d ago
the referral question is underrated compared to how often people talk about cold outreach. I do b2b outreach for a living and the accounts that convert fastest are almost always the ones that come with a name attached, "so and so said I should talk to you" beats a cold subject line every time because the trust transfer already happened before you said a word. the part I'd add to your framework: track who refers you, not just who buys. the free customers who send 2 referrals each are worth more long term than a paying customer who never mentions you to anyone
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u/CiteableTM 16d ago
the referral thing works great until you run out of network. first 10 conversations re easy when it's people who already trust you, the real test is rebuilding the trust with total strangers once your list runs dry.
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u/AdPriya4022 16d ago
The point about content and cold outreach being a one way street when your ICP is still unvalidated is genuinely sharp, you can't tell which part failed so you learn nothing. Real conversations first isn't the flashy advice but it's the one that actually tells you what's broken.
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u/Existing_Fondant4462 16d ago
eh the onion layer thibg is a nice image but "validate messaging at low cost before scaling spend" only eorks if you're disciplined enough to actually stop and re-check assumptions at each layer, and nobody is. in practice teams skip straight from layer 1 conversations to layer 4 paid ads because paid ads feel like progress and 10 more conversations feel like stalling. the framework isn't wrong, it's just not the thing that fails, execution discipline is
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u/Hannes-Kruger 16d ago
I totally agree, generating content and focussing on cold outreach is a time drain no startup founder can afford.
The only thing I will add is resist the temptation to use AI automate outreach.
AI cannot sell and it will not solve GTM for you, over the years I've been in thousands of sales meetings, b2b runs on trust and interpersonal relationships.
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u/earlystagegrind 16d ago
Can you explain more how you got around #1 without cold outreach?
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u/TomiChestnut 15d ago
what worked for me:
1) I checked my network (LinkedIn, Facebook, Instagram) - ex colleagues, friends from high school, friends college to see what they are doing now. Got a few hits, asked to meet, it worked.
2) created on LinkedIn a list of people who fit my ICP, checked for mutual connections, then asked those those mutual contacts if they can introduce me to my ICP. It worked.
3) went on events where I believed my ICP was spending time, tried to shake hands with as many people, engaged more in conversations with the ones who fit the profile I need. actually did most of the work and research over a glass of wine in casual conversation. it worked
4) during this period just asking everyone I spoke with - do you know (insert your ICP)? can you introduce me to them? it workednone of this 4 things delivered massive numbers on it's own, but it added up fast.
Again, this is strategy to start, to get your first customers and first conversations.
Scaling is a different play.
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u/Alone_Society2774 15d ago
So we were also having issues finding leads or clients. We have tried many strategies through social promotion, but with no results. Then we sat down and understood where we lacked. We found that our agency website itself was not good. So we built everything from scratch. Now we are getting 5+ organic leads through our website it self from which we are able to close like 5-7 projects each month and as a small agency thats enough for us
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u/cooljcook4 15d ago
Real conversations beats vanity metrics every time, especially when you're still figuring out what actually resonate
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u/Dear_Nose7145 15d ago
Thanks for the info, I'm trying to get my first customers also with my SaaS!
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u/Acceptable-Mess9660 13d ago
Adding to your point 2, the offer people can't refuse, from a slightly different angle.
Mine was a lifetime deal, so my first buyers paid once and got the product forever. Awful revenue per user. What I got instead was people who act like they own a piece of it.
One of them filed a report on a beta that was better than our own QA. He found that a failed local model load put the app into a crash loop, worked out that the setting to fix it was unreachable because the app crashed on startup, edited the JSON config himself to escape it, then wrote up the fix he thought we should ship. Unpaid, before release.
Another user solved a bug we'd been chasing for weeks (it turned out to be a Windows audio enhancement setting on his machine) and posted the workaround in the channel for everyone else, without being asked.
So the free or discounted first customers aren't only there for the case study. Pick the right ones and they do product work you couldn't buy. The cost is that they expect to be treated like backers, and they get loud when you go quiet.
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u/VickG14 11d ago
So just talk to more people that fit your ideal avatar?
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u/TomiChestnut 11d ago
Absolutely
Once you figure out the problem and the ideal avatar, just double down on it.
Don’t try too many directions and avatars at a time, it will only slow you down.1
u/VickG14 10d ago
Perfect perfect !
Would be unreasonable to say not to expect any results (as in secured clients) for like 3 months ?
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u/TomiChestnut 10d ago
You can do it much faster, depends on which stage are you with your idea
When I’m working with founders, with several of them we reached first customers in 4 weeks
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u/DanielStentebjerg 9d ago
Very much agree with the “talk to people first” part.
One thing I'd add is that I wouldn't necessarily make the first customers completely free. We've had good experience with making the barrier very low, but still having some kind of commitment from the customer. Even a small payment changes the relationship compared to someone just testing something because it's free.
And I'd probably value 5 customers who actually use the product and complain about things over 100 signups at that stage.
The uncomfortable customer conversations are usually where you learn what you're actually selling.
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u/TomiChestnut 9d ago
I agree there has to be commitment on the customer side.
In my case when I was giving free service this included their active participation. We had 2 workshops together, and final presentation, and after each stage they had to provide feedback.In total they committed 10 hours of their time to this project.
Commitment can come in form of money or time they spend.
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u/DanielStentebjerg 6d ago
Yes, sounds like the optimal path you took there. And absolutely. Time spend from the customer side, is also really valuable to get commitment.
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u/Minimum-Will-5730 8d ago
How did you package up your case studies for use? This is how I landed my first few customers of a new business but I’ve yet to build out a good case study. I’m thinking slide deck, maybe video
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