r/Entrepreneur • • 9d ago

Hiring and HR What do you do when a client wants one of your best employees removed?

49 Upvotes

I have an employee who consistently does good work, but a client has complained and wants them removed from the account. I don’t think the complaint fully reflects the employee’s performance, but I also don’t want to damage the client relationship.

How would you handle it, support the employee or honor the client’s request?


r/Entrepreneur • • 9d ago

Weekly Discussion Thankful Thursday: Free Resources and Tools | October 08, 2026

13 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 • • 10d ago

Best Practices How can you train a salesperson who is good, thinks they're the best, isn't, but COULD be?

24 Upvotes

I run a small outbound agency that does cold calling for B2B companies. One of my callers is doing ok. He books meetings and he's clearly capable. I like him a lot as a person and I want him to stay.

For comparison, my best caller handles 4 clients and fulfills every one of them properly while making fewer calls. This guy has 2 clients and needs a lot more volume to get there. The main difference is fundamentals. My best caller follows the script, especially the opener, and his conversations go further because of it. The other guy drifts from the script and makes up for it by dialing more.

For comparison on average my best caller gets through the opener 70% of the time while this caller gets through a little under 40%.

He can definitely be good. He's right there. I just don't know how to tell him he needs to be better without it coming across wrong.

I brought in an experienced cold caller to run group training twice a week, and most of the coaching gets met with objections. One of my other team members noticed that when the coach calls him out on something, he always has an explanation ready, like "well, that's because of this" or "that one was different." He isn't rude about it, but the feedback never really lands. It seems like he thinks he's already at his ceiling.

I am afraid if he doesn't adapt he needs to be replaced, which I don't want to do. He is not a dumbssa but the first step is just knowing he needs training.

For anyone who has managed salespeople:

  • How do you tell someone who's doing fine that they need to level up, without discouraging them?
  • How do you get past the objections when you're coaching? Is group training the wrong format for someone like this?
  • Have you shown someone their numbers next to a top performer's, and did it help or backfire?
  • Have you had someone like this turn the corner? What made it click?

Would appreciate any advice, especially from people who have run sales teams or call floors.


r/Entrepreneur • • 9d ago

Best Practices Do your clients know your payment terms before they sign, or only when the invoice arrives?

12 Upvotes

One thing I noticed in Accounts Receivable is that many payment problems start before the invoice. If terms only show up on the invoice, the client sees them as a surprise, and surprises get ignored.

The businesses that get paid on time usually state the terms early: in the proposal, on the kickoff call, and in the contract. Then a reminder is just following what was agreed.

How does it work in your business? Do clients see your terms before they sign, or only on the invoice? And has changing how you present them made any difference to how fast you get paid?


r/Entrepreneur • • 10d ago

How Do I? How to navigate a corporate take over?

38 Upvotes

A company I consulted for last year reached out in desperation. Basically, the way things ended was they were hitting a cash crunch and I offered to take a reduced salary for equity. The CEO declined and listened to the people I was warning him not to listen to.

Now, they're all gone. The only thing left is a million dollar saas company with no engineers and 1 CEO. The debt is almost half a million and the payments are preventing any opportunity for growth. He's basically treading water until one of the big customers leave.

But...

I do like the space and the relationships are not easy to get for SaaS sales.

I am an in a unique place because I have the money to invest and already know their code. They want me to be CTO and help save the company.

He knows he has to bring in investors and while I'm ready to invest, I don't have enough to do what I really want to do.

This guy needs to go as CEO. He should 100% still be director of sales and product, but he's not a CEO. I have enough money to keep us a float, but I'm not willing to make that investment if he's going to remain as CEO.

My thinking is to bring in a larger investor than me that will 'do the dirty work' because at the end of the day there is a good business here. I think if we can get rid of the debt and the CEO, this could be closer to a hundred million dollar company.

I'm going to start talking to my network of investors because I think this is a great investment for pennies on the dollar if we can get rid of the CEO but let me know what you think.

Have you ever been involved in something like this?


r/Entrepreneur • • 10d ago

Mindset & Productivity Do you game as an entrepreneur?

53 Upvotes

Yo guys,

I run a 6-figure agency, heading toward 7 figures soon, and I'm considering playing a video game to unwind and turn off my brain (sometimes it's hard to do).

In particular, WoW Forever, which is coming soon.

However, I'm worried it could ruin my drive to complete and achieve.

Some "thoughts" online suggest that if you point your urge for achievement/competition towards video games, you derive it from your business career.

If you game, how true is that for you?

I'm more than confident it wouldn't ruin my schedule, sleep, or anything else. I'm in a good spot on that front.

So I'm writing here to see if you guys game? How does it affect your business?

Cheers


r/Entrepreneur • • 10d ago

Starting a Business Think It's Possible To Find A Capital Partner To Buy More Rentals?

17 Upvotes

Wondering if it's common in RE investing to partner with someone who is willing to put up the money for down payments on rentals so we can do higher volume.

The division would look like..

One partner gets the hard money loan under their name to purchase the property, handles the rehab, gets tenants in, refinances out of the hard money loan under their name, and manages the property ongoing.

One partner funds the down payments for the hard money loans.

Obviously capital partner gets paid back right away after it's rehabbed and refinanced, and then whatever other kind of mutually beneficial arrangement they want to work out from there

Thoughts?


r/Entrepreneur • • 9d ago

Business Failures Watched The Odyssey. Shut down my second co-founded startup the next morning.

0 Upvotes

Last weekend, I watched Nolan’s The Odyssey. As a Greek, I’d been kind of avoiding it because I had mixed feelings about it, which is why I’m so late to the party.

It was great. But the character who really stuck with me was Agamemnon. I already knew the story, of course. Greek mythology was a big part of growing up. But seeing it on screen brought it back to me in a way I hadn’t expected. He sacrificed his own daughter for favorable winds, and I walked out of the cinema thinking about what commitment actually looks like for entrepreneurs in the real world.

Once I figured out what it looked like for me, I asked my cofounder to meet the next morning. I told him we weren’t at a point of real commitment to our project yet.

I was imagining tons of calls and emails a day, filling up the sales pipeline, turning the prospects we booked for demos into clients, and running their campaigns with maximum effort. Basically, doing whatever it took to get our B2B newsletter marketing agency off the ground.

We met after we both joined the Antler residency in Berlin and decided to try building something together there. For the past year and a half, he’d also been running his own newsletter on the side, which is where the idea for the agency came from.

The newsletter already brings in decent money, which he’s currently reinvesting into its growth. The brands we had been chasing as agency clients were literally approaching him and offering to pay directly for advertising in his newsletter.

I was asking him to make a sacrifice while those same brands were throwing money at him.

Any of us would probably choose the easier, proven path. Understandably, that was the choice he made too. It became clear that the project was over, so we shut the agency down in that same meeting and sent apologies to the prospects already in our pipeline.

That was co-founded startup number two since April, and project number seven since I quit my full-time job a little over a year ago.

The first co-founded startup was an AI tool for customer success teams. We were developing it alongside a specific customer, basically like a design partner. I may have even posted here to complain about it at the time.

They kept reassuring us, “Yes, this is interesting,” “Yes, you should build this,” and “Yes, we’d pay for this.”

We developed the project they said they wanted, but apparently didn’t need badly enough to pay for. They never approved a budget, and we eventually had to kill it too.

The AI tool and the solo projects that came before it didn’t turn into successful companies, but the experience was a big part of why I earned a spot in Antler’s Berlin residency.

The founders and partners here get it. From day one, we were told that teams would change, and our team was actually the first to part ways.

My parents don’t get it, though. They’re scared for my future and don’t understand why I keep changing teams or why no project seems to stick. Honestly, when they call and I hear the confusion in their voices, it hurts almost as much as the startups failing.

I have about 90 days of runway left before I need to start selling assets to keep funding this journey. At the same time, I’ve reached the final stage of an interview process with an incredible company and team for a role offering compensation that is almost unheard of by European standards. And yet, I’m not sure I want the job.

These past 13 months as an entrepreneur have been the life I always dreamed of. I’m exactly where I want to be, minus the “no revenue” issue, of course.

So today, I started again, solo, with an e-commerce idea I’ve had for a while but kept dismissing.

The concept is something I came across a few months ago called “buy now, pay maybe.” Instead of offering every customer the same discount, some customers have their purchase refunded after buying. I spent most of today researching the market and found a specific angle that I think could differentiate it from the existing options available to e-commerce stores. Whether that difference is valuable enough is what I still need to validate. I’ve vibe-coded the marketing website, but I haven’t built the actual product yet.

My previous projects taught me not to confuse “this is interesting” or “I would pay for this” with actual validation. There is no real validation until there is a signed commitment or money in the account.

This time, I’m doing the outreach first and will only start developing if a merchant commits to a paid pilot or signs an LOI with a specific budget and timeline.

Before I make the same mistake again, I want to challenge the assumptions behind the idea.

For those of you who run an e-commerce store or have worked closely with one: how do you decide when to offer discounts? What do you dislike about traditional discount codes? Have you ever experimented with surprise rewards or refunds, and did they improve conversions or repeat purchases, or did they just reduce margins and add complexity?


r/Entrepreneur • • 11d ago

Lessons Learned What AI tools have changed your life as an entrepreneur?

298 Upvotes

Hi all- I keep hearing AI tools are here to change the world but I feel like I am not sure what has changed my life that much. I do use ChatGPT and Claude daily and its definitely useful but not sure ifs life changing.

So curious to the experts here, what AI tools have changed your life as an entrepreneur?


r/Entrepreneur • • 11d ago

Weekly Discussion Talent Tuesday: Services and Collabs | October 06, 2026

17 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 • • 12d ago

How Do I? 12 years running a B2B company in the Caribbean, ~$1.6M ARR, and I've never had a mentor. How did you find yours?

84 Upvotes

I've run a fleet tracking company for about 12 years. We sell GPS tracking and AI dashcams to commercial fleets, mostly across the Caribbean, with a smaller operation in Colombia. We have around 370 clients, roughly $1.6M ARR, and we're on track for about 30% growth in the Caribbean this year.

On paper it's going fine. But I've reached the point where I don't fully trust my own read on the business anymore. I built most of it by figuring things out as I went, and I'm starting to suspect some of what I see as normal is actually a blind spot.

Here's a concrete example. Almost half our clients, about 170 of 370, pay late. They don't default, they're just consistently late. We get paid by wire transfer because that's how most businesses in the region pay, and we bill across 20+ territories with different banks and payment habits. I've lived with this for so long that I honestly can't tell anymore whether it's just the market or something I've been tolerating that a more experienced operator would have fixed years ago. I suspect it's the second.

That's the kind of outside perspective I'm looking for. I want someone who has been further down the road and can look at what I'm doing and tell me what I'm not seeing.

A few questions for anyone who's been here:

  1. Mentor or coach? I don't know if I need a founder who's done it, a paid coach, or both. If you've had both, what did each give you that the other couldn't?
  2. How did you find yours? And if it was someone senior who didn't owe you anything, how did you make the ask?
  3. Has anyone dealt with late payments in a market where wire transfer is the default? What actually changed client behavior?
  4. Looking at my situation from the outside, what would you be asking me?

I'm not selling anything and I'd rather not get coaching pitches in my DMs. I'm just trying to learn from people who've been in this spot. Happy to answer questions about selling B2B in the Caribbean if that's useful to anyone.


r/Entrepreneur • • 12d ago

How Do I? How do you tell when a big customer is pulling your business in the wrong direction?

32 Upvotes

“Listen to your customers” gets complicated when one customer is worth enough money that their requests start carrying more weight than everyone else’s.

A request comes in that’s slightly outside what you normally do. It seems reasonable, and keeping the account happy matters, so you agree. Then there’s another exception. Eventually, your team is running a separate process for that customer, but everyone still talks about them as one of your best accounts because of the revenue.

I think the difficult part is that this can also be how a business discovers a better offer. A customer asks for something you hadn’t considered, you figure it out, and other customers end up wanting it too. Refusing everything outside the original scope would close off some useful opportunities.

The test I keep coming back to is whether you’d want ten more customers just like them.

That forces you to consider what happens after the sale. The contract might look great while the people doing the work are spending half their week handling exceptions. Or the account might be difficult because you’re learning something that will make the next ten easier.

Those situations deserve different decisions, and revenue alone won’t tell you which one you’re in.

Before calling an account a success, I’d want to hear from whoever actually has to deliver on it. Especially whether the extra work is becoming something repeatable or still depends on someone dropping everything whenever that customer calls.

For people who’ve been through this, what helped you recognize the difference between a demanding customer worth building around and one you needed to stop accommodating?


r/Entrepreneur • • 12d ago

Weekly Discussion Monday mentorship: ask anything | October 05, 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 • • 13d ago

Weekly Discussion Sunday Steam: Vent It or Roast It | October 04, 2026

34 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 • • 14d ago

Starting a Business YouTube video production for B2B companies

33 Upvotes

I'm thinking of starting a YouTube video production service for B2B businesses. Wanted to get some honest feedback before I start!

The idea is to have the company's own experts (an engineer, a technician, a sales rep, whoever actually knows the answer) answer the real questions their customers ask before buying, on video. Things like "how much does X cost", "X vs Y, which one do I need", "what goes wrong when you install X". I collect the questions in a short call with the sales team, record a remote call with the expert, cut myself out in editing, add screen recordings of the product if needed, and publish it on the company's YouTube channel.

The point is that the video is useful even with very few views I think. The sales team can send it to a prospect who asked that exact question and over time it can rank on YouTube and Google for searches people actually make.

In addition to that, the added value is the content repurposing: turning each video into vertical clips with subtitles, LinkedIn posts, a newsletter, a blog post, etc., so the company gets more content out of a single recording.

A few things I'm unsure about and would love feedback on:

  • Would they prefer remote recording or someone coming to their office with a camera (this was originally my idea to add some extra value to the service)?
  • Is "videos your sales team can use tomorrow" a stronger pitch than "grow your YouTube channel"?
  • Which industries do you think this would work best for?

r/Entrepreneur • • 14d ago

Starting a Business Is it me or is running startups is so hard these days

98 Upvotes

​

Been in this sector for over a decade. Feels like things are getting harder and much more competitive. I don't even bother joining accelerators because of their intake stats are mind blowing.

We got enough traction with patent but maybe still not good enough


r/Entrepreneur • • 14d ago

Lessons Learned Founders who’ve used Reddit for idea feedback: how did your last attempt go?

21 Upvotes

I’m researching how entrepreneurs get feedback on business ideas from people in their target market.

If you’ve tried doing that on Reddit recently, what happened? Which audience were you trying to reach, what did you post, and did the responses help you make a decision?

If it didn’t work, what did you try next? If it worked well, what made the difference?
I’m exploring a business in this area and want to understand people’s actual experiences before proposing anything.


r/Entrepreneur • • 14d 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 • • 14d 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 • • 14d 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 • • 15d 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 • • 16d ago

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

58 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 • • 16d ago

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

17 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 • • 16d ago

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

90 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 • • 16d 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.