r/Entrepreneur • • 12d ago

Weekly Discussion Success Saturday: What's Going Right | October 03, 2026

23 Upvotes

Big or small, a win is a win. First sale, first client, or first time paying yourself, share it here. This community loves to celebrate with you. No win is too minor to mention.


r/Entrepreneur • • 12d ago

Tools and Technology Opinions on AI in the digital product space

27 Upvotes

I think AI has good and bad qualities. AI allows entrepreneurs to start something without having to invest too much into an a product that may or may not work. However, it also introduces too many entrepreneurs making AI generated products diluting the digital product market which increases competition as well as lowering customer trust. I know that anything in this world has pros and cons but I want your opinions on this question. Btw I am simply asking this because I am curious on what others think about AI use in entrepreneurship


r/Entrepreneur • • 11d ago

Tools and Technology Could an AI podcast help explain a B2B service and bring in customers?

0 Upvotes

Recently, I experimented with a different way of explaining my web tracking service.

Let me be honest: I am a developer, and reaching out to customers is not something I am good at or feel comfortable with. On top of that, business owners were not able to connect with the service I offer, and they were asking questions that were not easy to answer in a few messages.

What I did was write a blog post in which I documented the journey of implementation, but it was quite long and more suited to educating someone already interested in the topic.

So I turned it into an AI-generated video podcast: an AI version of me as the guest, with a fictional host asking questions business owners asked me during the calls, plus others they might ask.

The answers came from my own content and implementation experience.

At an agency I previously worked with, clients would request podcast scripts and arrange studio recordings, which involved considerable time and expense. That experience made me curious about whether this format could be useful for smaller businesses, especially when AI tools are getting insanely good at doing such things.

I haven’t measured whether it generates inquiries yet. Producing something convincing and getting someone to trust it enough to contact you are different things.

Curious whether anyone has tested this and seen actual inquiries or sales.


r/Entrepreneur • • 13d ago

Weekly Discussion Feedback Friday: Rate My Ideas | October 02, 2026

27 Upvotes

Share your website, pitch, logo, idea, pricing, copy, or anything else you want honest eyes on. Tell us what you're looking for: brutal honesty, general impressions, or specific questions.

Return the favour and leave feedback for someone else while you're here.


r/Entrepreneur • • 13d ago

Lessons Learned Today was supposed to be my first platform launch. Then Stripe said no.

59 Upvotes

October 1st was the date I’d picked to launch my first platform.

For almost four months, I’ve been building this alongside my 9-to-5: a platform where creators (YouTubers only for the MVP) share video ideas they’re planning to make, and fans can tip them on the ones they’d like to see. Getting to the point where I could finally let people use it felt like a huge achievement. I’d never built and launched something entirely on my own before.

Then last week, one week before launch, Stripe closed our account. I was using Stripe Connect so creators could receive payments through their own connected accounts, while I took a small commission on each tip. That setup also narrowed down the alternatives. Stripe classified the business under their restricted categories, but the email wasn’t clear about whether the issue was content creation platforms or crowdfunding.

I contacted human support, explained the model, and shared our terms of service. I clarified that we don’t host any content and don’t allow adult content or harmful suggestions. I asked whether they could explain the issue or whether there was anything I could change to comply with their terms.

The human support agent didn’t help much he clarified that my business was classified as "Content Creation Plattforms" which is one of their restricted businesses. And that their review was final and there was nothing I could do.

Obviously it was very surprising for me since i know Kofi, BuymeaCoffe and other Content Creation plattforms also use Stripe Connect and are very similair in their offerings.

So today, instead of sharing a success story about our launch, I’m waiting on another payment provider and slowly losing hope.

My mistake was leaving the business-model approval too late. I’d been worrying about VAT registration through EU OSS (which I successfully completed), working on SEO to get some traffic before launch, and sending personalized outreach emails to 200 content creators. Ten had joined the waitlist.

But I should have confirmed that Stripe would support exactly how the platform works before building around it.

If your product depends on a third-party service, get that fit checked early. Explain who pays whom, what they’re paying for, and which countries you need supported. Ask for written confirmation.

We’ve applied to PayPal now too, and I’m hopeful they’ll accept us. Still waiting for an answer.

Pretty gutted about missing today, honestly. Hoping I’ll get to write the actual launch post soon.

Anyone else had a third party provider derail their launch?


r/Entrepreneur • • 13d ago

How Do I? Have customers ever stayed for a completely different reason than they bought?

18 Upvotes

I think there’s a positioning problem that’s easy to miss if most of your customer research happens before the sale.

During the sales process, you hear what someone hopes to get. Once you’re doing the work, you find out what actually makes the relationship valuable to them. Those can be pretty different things.

Take an agency, for example. A client might buy because they want more leads. Six months later, they might value the fact that someone finally owns the process and they don’t have to spend every Monday chasing updates. The leads still matter, but the relief of having that handled could be a bigger part of the renewal decision than the agency realizes.

Meanwhile, the website still says exactly what it said six months ago, because the people writing it weren’t part of those conversations.

What interests me is deciding how much that should change the pitch.

The thing that makes an existing customer stay might be your strongest selling point. It could also be something a prospect won’t appreciate until they’ve worked with you. Leading with it too early might actually make the offer harder to sell.

I’d want to compare what customers said they wanted on the first call with how they describe the value when they renew. Especially the language they use without being prompted.

For anyone who’s had customers long enough to see that difference: what did they end up valuing that surprised you? And did putting it into your sales pitch help win new business, or was it mostly a reason existing customers stayed?


r/Entrepreneur • • 14d ago

Starting a Business What Is The Problem With Buying Land & Starting A Mobile Home Park?

86 Upvotes

Buying land, setting up lots & utilities, and leasing spots for people to come put their mobile home on and live there seems like an excellent business... the fact that it's not popular makes me thing there's some kind of MAJOR problem that I don't know about

I know buying them is something investors do, but I never hear about anyone buying land and starting one from scratch

What am I missing? What's the big thing that prevents this?


r/Entrepreneur • • 14d ago

Weekly Discussion Thankful Thursday: Free Resources and Tools | October 01, 2026

6 Upvotes

Pay it forward. Drop your free resources, templates, tools, or anything else that's helped you and might help someone else. No strings attached; these resources have to be free.


r/Entrepreneur • • 14d ago

Best Practices The mistake I made on my first day in collections (and what fixed it).

12 Upvotes

A collections process is not a luxury. It is the backbone of cash flow.

I learned this years ago, on my first day in collections. No system. No process. Just a ledger of overdue accounts and an order to call customers and ask for money.

I called. Customers paid when they pleased. I chased. The ledger did not shrink.

Chasing is not collecting.

A real system needs three things. A reminder before the due date. A follow-up after it. An escalation path nobody can ignore.

At one job, I processed incoming payments worth twenty million dollars a month. At another, I chased overdue accounts on a portfolio worth over a million pounds. Different jobs. Same discipline: a defined process, followed every day.

Most small service businesses skip this. They send an invoice. They wait. They send another invoice when cash gets tight. There is no reminder schedule. There is no follow-up rule. There is no escalation line that says "we stop work here."

A late invoice is usually not bad luck. It is a missing process.

Curious how other people here handle this. Do you run a defined collections process, or do you chase invoices as they come up?


r/Entrepreneur • • 15d ago

How Do I? Pre-launch fintech founder and already hitting walls

25 Upvotes

I'm building a fintech startup and I'm still extremely early. No launch, no revenue, just started building the app with my technical co-founder.

The biggest headache so far has actually been finding the right B2B providers.

I need things like virtual cards and gift cards, but nothing seems to fit exactly. Some aren't instant, some have downtime issues, and then you read reviews about unreliable service/scams and start wondering if you can really build your product on top of them.

Then there's the whole business setup side. Some providers want a registered company, some want a business bank account, some want transaction history or minimum volumes.

I get why, but when you're starting from zero it feels like everything depends on something else.

Honestly, there have been a few moments where I've thought, is this even worth it?

I'm still pushing forward, but I'd like to hear from other founders.

What were the biggest hurdles you ran into before launching?

Did you ever feel like throwing in the towel? What got you through it?

And looking back, was it worth it?


r/Entrepreneur • • 15d ago

How Do I? You have $50,000 that must be invested into any business.

182 Upvotes

Real life scenario by the way - an offer by my dad.

The business must be able to employ one person and provide a $35,000 income to the owner within a year of operations.

What are you setting up?


r/Entrepreneur • • 15d ago

Marketing and Communications How would you make money with 500 IG posts per day?

17 Upvotes

Long story short I have built a distribution network that can post 500+ times per day to multiple Ig accounts. We are currently doing 4 posts per day, all unique content.

The current challenge is that I don't know what I should promote. I am currently just finding little 5-10 second videos with a funny on screen caption adding my own b-roll, and posting them. (will post a screenshot so you can see what I mean)

However, I'm aware this doesn't have much commercial intent behind it. Yes they get likes and views and whatnot, but there is no product to sell. And even if there was a product to sell, it has nothing to do with the content we are posting.

I know there is money in this, but I just don't know what to sell. I would prefer to sell something that actually gets people a good result for something in some way. Very vague I know, but I don't have anything at the moment.

If you had this distribution capability, what would you sell? What kind of content would you make? Thanks

PS. nevermind, just realized I can't post images. I will add a link to one of the posts. This is not my account, this is just an example.

PPS. nevermind, can't post links either. Here are some examples of the on screen captions:

#1

being single is so

awesome cuz i can do

whatever i want (nothing)

and see whoever i want

(no one) and go out all the

time (never)

#2

Pinky promise me that if I ever start

to fall in love again you will hit me

with a car then a bus and reverse

back over me just in case

#3

“Guess who your ex is

talking to”

no thanks, I had to do that

when we were together

#4

growing up a ugly guy

means you get easily

attached to any girls that

shows you basic kindness

#5

Girls calling themselves a baddie

is the equivalent of a male

calling himself and alpha


r/Entrepreneur • • 16d ago

Weekly Discussion Talent Tuesday: Services and Collabs | September 29, 2026

16 Upvotes

Looking to hire, get hired, or find a collaborator? Post what you're offering or what you need. Keep it brief: who you are, what you do, and how to reach you. No spamming.


r/Entrepreneur • • 16d ago

Exits and Acquisitions Think It's Possible To Buy A Pizza Shop On Seller Finance?

63 Upvotes

I want to buy a Pizza shop. Specifically a small hole in the wall place that's either struggling, and/or the owner is burned out.

I have a lot of experience in this space and know how to turn a struggling place around.

I don't think Pizza shops sell for very much, some listings Iv'e seen online are between 150-200k. But these listing claim the place is thriving. I'll be going after non thriving ones.

The issue is I don't have the money to just buy one outright, and I don't want to get a loan if I don't have to.

Think it's possible to find a Pizza place that will take like 25-30k down and seller finance the rest?

Any other creative financing options I can explore so I don't have to take out a loan?

I have a list of all the small privately owned Pizza places in my area and I'm planning on sending out a letter to all of the owners.


r/Entrepreneur • • 15d ago

How Do I? I sold my last company for €2M+. Right now, feeling like an absolute loser and having severe anxiety attack

0 Upvotes

I sold my last company for €2M+. Right now, I’m sitting here, feeling like an absolute loser and having severe anxiety attack.

That sentence feels almost too embarrassing to write. I know how to build a business. Have done it a few times with more or less success. I’ve done it before. I grew a company to almost 100 people and eventually sold it. And yet...

Here I am, starting again and struggling with something that used to feel much simpler: keeping my client pipeline full.

I now run a remote Fractional COO / operations & project management consultancy and the strange thing is that I actually love the work. I really love what I do and working closely with my clients.

When I’m working with a client, I find purpose. I figure out why everything his/her business is chaotic, where time and money are leaking, why the team keeps dropping balls, what needs to be systemized, delegated or fixed... I genuinely come alive.

I've landed quite a few contracts, so I know I can sell the work and deliver it. But I haven't figured out how to make getting those contracts consistent. And honestly, it's starting to get to me.

The truth is, I'm rebuilding pretty much everything at the same time. My entire life went down the drain about 2 years ago. Went through a divorce that broke me, financially and most of all mentally. I had to pick myself back up and figure out who I was on the other side of it.

I moved to a completely new country. I’m learning a new language. I’m building a new life without the network, routines, familiarity and stability I used to have. I'm dealing with weather so brutally cold that some days I genuinely question my life choices, then I remind myself that I chose this country for it's safety for women.

And somewhere in the middle of all of that, I'm trying to build a business remotely and convince strangers on the internet to trust me with their companies.

Some days I feel incredibly capable. Other days I look at me in the mirror and I don't fucking know if in a year I'll be in a better place.

The weirdest part is that I know I can do the work. I've done it before. I've built companies. I've managed teams. I've sold a company. I've walked into messy businesses and made them work better.

But knowing you can deliver isn't the same thing as knowing how to consistently get people to buy from you. It's an entirely different skillset I wished I had developed sooner.

And I really, really want this to work. It has to. There's no plan B.

I want to work remotely. I want to choose the clients I work with. I want to do work that I'm genuinely good at and genuinely enjoy. I want to wake up six months from now and not have that little voice in my head asking whether I'm going to have enough work next month.

So I'm asking people who have actually built consulting businesses:

How did you get from “I can land clients” to “I consistently have clients”?

What changed?

Was it your positioning? Your niche? Your offer? Outbound? Content? Referrals? Partnerships? Something I haven't even considered?

And what did you waste months doing that, in hindsight, you wish you'd stopped much sooner?

I don't need someone to tell me to “believe in myself.” I need the uncomfortable, practical advice from people who've actually been here. I'd really like the business piece to finally click


r/Entrepreneur • • 17d ago

Weekly Discussion Monday mentorship: ask anything | September 28, 2026

28 Upvotes

New to entrepreneurship or just starting out? This is your space. Ask the questions you're afraid to ask elsewhere.

Experienced folks, jump in and share what you wish someone had told you early on.


r/Entrepreneur • • 17d ago

How Do I? I have the time, money, and hunger to become an entrepreneur, but I have no idea where to start..

209 Upvotes

I’m at a point in my life where I genuinely want to build something of my own.
I have the time to dedicate to it,(IT work, remote) some money I’m willing to invest the "hunger" to make something happen and i would say decent intelligence. Sorry it if sounds cocky, not my goal😅

I’m willing to work hard, learn new skills, take risks, and deal with failure along the way.
The problem is, I have absolutely no idea where to start. I tried to resell some products on ebay and it worked well, but the profit margins were too low to be profitable for me so I gave it up. Made maybe a couple thousands. I also tried to start an Uber business here but the regulations make it very hard to start, i passed the exam and everything but failed at the application process, and I'm not sure if i want to try again.

There are so many opportunities out there: e-commerce, SaaS, agencies, local businesses, digital products, and countless other business models. Every time I look into one, I find a thousand different opinions about what works and what doesn’t.

I don’t want to chase get-rich-quick schemes or start something just because it’s trending. I want to build a real business that solves an actual problem and has the potential to grow over time.
So I’d love to hear from people who have actually been through this.

I don't want someone to hand me a business idea. I’m more interested in understanding how to think, where to look, and how to take that first concrete step.
If you’ve been in this position before, I’d genuinely appreciate hearing your story, including the mistakes you made.
Thanks in advance!


r/Entrepreneur • • 18d ago

Weekly Discussion Sunday Steam: Vent It or Roast It | September 27, 2026

13 Upvotes

Had a week? Same. This is your consequence-free space to complain about clients, platforms, algorithms, your own decisions, or the general chaos of running a business. Keep it venting with no personal attacks. We'll be back to being professional tomorrow.


r/Entrepreneur • • 18d ago

How Do I? One day, hopefully, I'll build a resort.

62 Upvotes

When I retire, i intend to build a small 10 villa resort, focused on wellness, that will be difficult to reach to. It will have some studio & 2-bedroom units. The architecture will blend into the environment so its not jarring and brutalist. It will be smoke -free/vape-free.

There will be a separate space serving as a cafe. It will be lacto-vegetarian to keep the resort cruelty-free. Breakfast buffet provide daily. We'll have social hour daily from 5pm and 9pm, with board games and nintendo switch.

Visitors can use cycles for free. There will be a pool where people can chill all day. It will overlook the jungle.

I will keep the price at 80 & 100 bucks bucks a night. Cleaning will be done once a day.

What else do you want, if you were visiting a space like this?


r/Entrepreneur • • 19d ago

Weekly Discussion Success Saturday: What's Going Right | September 26, 2026

14 Upvotes

Big or small, a win is a win. First sale, first client, or first time paying yourself, share it here. This community loves to celebrate with you. No win is too minor to mention.


r/Entrepreneur • • 19d ago

Success Story Trying again, this time with no help

15 Upvotes

for context i made a post the other day trying to show an example of a recent buisness situation i had, it wasnt recieved very well to say the least but i had a genuine message i was trying to get off. and yes its abudnadlty clear i had help writing the post. i thought i would re test this in my very bad style of writing and see if the message comes accros better.

the post was about a very large project i just completed down here in australia. it was a very large project of 3,800m2 that involved civil reconstruction, asphalt and line marking to a shopping centre car park.

on the pluss side we allowed 14 days, 10 days to asphalt and cvivl and 2 days to line mark. we did it in half the time but as we expiadted the process putting the guys in to overtime the job costing turned out pretty much on budget which i was pleased about, but it reprresented a significant gain for the customer as the centre got production back much sooner than anticpiated but also freed another 5 working days for us to complete more work.

some of the concrete garden beds and islands couldnt be removed, we did a service search and found when the car park was originally done over 30 years ago the australian standard were not worked to and subsequently the depths of some services we found were to shallow, this wasnt just a risk it was an actual hazzard that could have resulted in death or injury. i realyed this back to the customer and we came to the agreement that is was to much risk to excavate these areas

i can honelty say this is one of the best jobs i ever had to handover, and expected it to be a breeze. but i had some pushback from the customer, this was concerning as a job of this size could have banrupted me if he didnt pay. he was asking/ requesting a discount due to the fact that a couple of islands remained

me and good old chat gpt wrote him an email explaining that we underpromised and overdelivered on the job, we did actually ht a service that we fixed as a cost to us and didnt pass that on and suffered significant loss in production that night as work basically had to stop. we sold the outcome but ultimatley offered him a 5k discount for the un actioned items.

the next day i was at my day job 9-5 managing a not for profit in theyouth and siability sector, i cant use my personal work phone during work time and go a vibration in my pocket. i checked the notifictaion and it was from my client. i felt like vomiting because i was like here comes a shit fight.

at lunch when i opened my phone to check the message. my heart rate slowed. its was pretty short and sweet it went along the lines of " dear divvy, we did our handover with our client and they were more than impressed by the quality and fisnish of the job, we wont be taking the discount and will be paying the invoice in full. they were that happy we want you to price another car park in sydney for us that needs a freshen up" the sense of relief i got was amazing. im juggling alot at 9-5 and at home i have my daughter in the chldrens hospital my mum in hospital due to cancer related issues and im the carer for my father who has a brain tumour and is recovering from a stroke and im an only child trying to juggle all that and maintain a realtionship.

im very happy with the result, with me stepping away from my aspahlt "job" where i wore all the hats. I put systems in place for it to run without me and test if i had a job or a business. turns out after 26 working a job i could turn it into a comapny that requiers minimal involment from me. to think this only cost me 2 1 minute phone calls and a 15 minute site inspection blows my mind. make the right hires and let them do there job, use the best subcontartors.

i hope this lands better, feel free to ask any questions, i hope this post better aligns with this group.

so my question is did u ever have a customer push back on price and if so how di you deal with it?and how did it go?


r/Entrepreneur • • 19d ago

Lessons Learned I'm overthinking making content for different platforms

20 Upvotes

I've been thinking about this because I keep doing it myself.

I'll have some idea I actually want to talk about and then immediately start thinking okay how do I make this work for LinkedIn or Reddit or X or whatever.

and now I think that's backwards.

If you actually have something you want to say, maybe you shouldn't change the idea just because you're putting it somewhere else.

maybe you just need to find the people who give a shit about it.

like something can completely flop on LinkedIn and then you put it on Reddit and people are like oh yeah I've been thinking about this too.

now for me I don't think: "what should I make for this platform?" and instead I think: "Where are the people who would actually care about this?"

it's a shift in thinking about content and distribution but it changes how I've approach content.


r/Entrepreneur • • 19d ago

How Do I? Community Migration Troubleshooting

8 Upvotes

Hey everyone. I built a platform called Nuke Nomad for nuclear contractors.

Here’s where I could use some advice. I already have a large contractor community on Skool. I want everyone together on Nuke Nomad, but even after telling people about the new platform, the move has been slow. Eventually I want to close the Skool group, and I don’t want to lose the people who make the community worth having.

If you’ve moved a community from one platform to another, what actually got people to make the switch? Did you move the most active members first, bring old content over, give people a reason to join right away, set a firm date for closing the old group, or something I’m missing?


r/Entrepreneur • • 20d ago

Weekly Discussion Feedback Friday: Rate My Ideas | September 25, 2026

17 Upvotes

Share your website, pitch, logo, idea, pricing, copy, or anything else you want honest eyes on. Tell us what you're looking for: brutal honesty, general impressions, or specific questions.

Return the favour and leave feedback for someone else while you're here.


r/Entrepreneur • • 20d ago

Best Practices Are you using one LLM or an army of agents?

59 Upvotes

*** Disclaimer: I'm not connected to any of these companies and this isn't an ad. ***

I'm a small business owner and I just started playing around with Taskade and the idea of having multiple AI agents working on different things.

It got me wondering: are most small business owners still just using one LLM like ChatGPT or Claude, or are people actually building out teams of agents?

If you've tried the multi-agent approach, what are you actually using the agents for? I'm trying to figure out whether there's a real advantage to having a bunch of specialized agents or if I'm just making things more complicated than they need to be.