r/Entrepreneur: Most Popular Posts Last Month
What r/Entrepreneur, a place for people starting or growing any kind of business, upvoted, argued about and asked for help with in September 2026. Built from every post that stayed up that month.
- Posts
- 141
- Posts a day
- 5
- Typical upvotes
- 14
- Typical comments
- 32
260 posts were submitted and 43% were removed by moderators or Reddit. Everything below is from the 141 that stayed up.
“Typical” is the median post. Updated monthly; this edition: September 2026.
Top 25 r/Entrepreneur posts in September 2026
Sorted by upvotes. Titles open the thread on Reddit.
- 1What’s an employee appreciation gift people actually liked?
I have a team of around 100 people and I’m planning an appreciation luncheon for the holidays. We’ll already have food and recognition, but I’d like to give everyone something useful without spending a fortune or…
206244Sep 23Hiring and HR
- 2Business is failing. No idea what to do next.
Hey everyone. I'm 25, and since I was 19, I ran a web design / SEO business. It changed a few times from being a general digital marketing agency, to a trades focused web design agency... etc. I focused on generating…
205188Sep 7Business Failures
- 3Why do people sell startups that are already making decent money?
I keep seeing listings like: \- profitable for 2+ years \- low expenses \- growing revenue \- owner only works a few hours a week And then...selling for $60k. My first thought is always: if it's really that good, why…
203102Sep 22Best Practices
- 42008 Crash. What business booms in economy downturn? Was your business affected?
2008 Crash. What business booms in economy downturn? Was your business affected?
198130Sep 17Success Story
- 5You have $50,000 that must be invested into any business.
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?
134129Sep 29How Do I?
- 6Do most successful founders end up without a family life
Not sure if this is real or just what I'm seeing. Most of the founders I know personally, and almost all the ones I follow online, are either divorced or never married. When you talk to them, nothing domestic ever…
11582Sep 20Lessons Learned
- 7Business is tough...
I had a multi million pound business until COVID wiped it out. I tried to rebuild as web dev, then AI came along. I built a product for a niche and was going well but, rather naively, we had 2 clients and they pulled…
9881Sep 1Business Failures
- 8One short drama made our 5-person team $120k in 30 days
We’re a five-person team based in LA, and one of our short dramas did a little over $120k in gross viewer revenue during its first month on FlexTV. Before anyone gets too excited, that is definitely not $120k sitting…
9332Sep 20Success Story
- 9I have the time, money, and hunger to become an entrepreneur, but I have no idea where to start..
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…
88108Sep 27How Do I?
- 10Now that anyone can build a web or mobile app, what's the real competitive advantage?
With Claude Code, anyone can now build the service they want, right? Looking at the communities, people really are trying a huge number of new things. If anyone, not just developers, can build these services on their…
84166Sep 18Mindset & Productivity
- 11Scared of success?
Has anyone else been kinda scared of success? In terms of growing really big, going viral online, etc. To preface, I have not started selling, I am only working on product development now and figuring it out. I am low…
6886Sep 15Starting a Business
- 12Running a business has left me with zero time where my brain is actually quiet
Working means screens all day. The second I stop, the phone is in my hand. Not because I want it. My brain just can't sit still at that point. Some of it is FOMO. Something moves in my space and I didn't see it, so I…
6766Sep 18How Do I?
- 13What is the best way to prepare yourself to own/run a business?
I’m going to be starting a CPG business (selling online). I want to make my first step into product development, but I always get kinda scared once it’s “done”, because then i’m like “now what”. Should I start posting…
6672Sep 8Starting a Business
- 14How does a serious company get taken seriously in all this AI fog?
Before I get bombarded by negative comments, I can see how AI has made entrepreneurship much easier in a lot of ways, like build products faster, do research much quicker, automate repetitive tasks, use AI agents for…
6384Sep 25Starting a Business
- 15How do I get the capital to start again?
Short back story. I've made 999silver jewelry for years. Had a good two year run with an online business that took off , personal stuff made my brain broken & I let everything crumble. Had to sell my equipment and all…
6353Sep 16Starting a Business
- 1618M have been running a ~25-30k/mo ish business now for 7-8 months and finally feel like I am in the moment right before I scale up
I first started a cold calling agency at the end of january of this year, which is also when i got my first client. After client 1 figuring out how to get a steady flow of meetings was extremely hard, but I eventually…
62113Sep 3Operations and Systems
- 17Think It's Possible To Buy A Pizza Shop On Seller Finance?
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.…
6074Sep 28Exits and Acquisitions
- 18Taking the leap
Putting in my two weeks notice on Tuesday. May end up being a bad decision, but I’m ready to either succeed or fail with the only person to blame being myself. I need to know what it’s like to hold my own fate in my…
6063Sep 5Starting a Business
- 19What do you think is the most advantageous career going into entrepreneurship?
The answer is probably very industry-dependent but overall, maybe sales? Design and marketing? My background is in design & marketing, then went on to work on tech UX strategy, and I feel like it’s given me a huge…
5966Sep 6Recommendations
- 20I won a contract that could double my revenue, but I don’t have the staff yet. What would you do?
I won a contract that could potentially double my revenue, but I don’t have the staff in place yet. I don’t want to hire too early and carry payroll, but I also don’t want to wait and end up scrambling when the account…
5378Sep 15Growth and Expansion
- 21Rich uncle wants to help me to start a business but i don't know what...
I have an uncle who has multiple businesses. Hes already a millionaire and i guess hes bored. He wants to support me (i live in another country, hes outside of EU) to start something myself. I guess he wants a…
5185Sep 22Starting a Business
- 22What’s one thing you wish you knew before starting your business?
I’ve been thinking about how different entrepreneurship looks from the outside compared to when you're actually in it. Before starting, most people focus on the big things-getting customers, making money, building a…
5163Sep 3Lessons Learned
- 23Am I Crazy For Wanting To Raise Money To Build A Racetrack In Socal?
I'm a car guy in SoCal There's basically 2 circut style tracks here where people can go track their car. One is like 4 hours away from SoCal where most of the car scene is, and it's a Club that has a $175k initiation…
5083Sep 10Starting a Business
- 24Founders who can't sell: what did it cost you to find someone who can?
I build, I don't sell. So what works better: going direct to one company and sharing profit with a single contact there, or using a sales partner? Tell me which one you chose, and how long it took you to know whether…
5056Sep 8Best Practices
- 25Nobody tells you that going global also means your money starts going everywhere
When we first started selling internationally, I assumed finding customers would be the hard part. What I didn’t expect was how annoying the money side would get. Customers paying from one country, suppliers in…
4735Sep 7Growth and Expansion
What people asked about or struggled with
Questions, complaints and “is there a tool for…” posts with the most discussion. A post with dozens of replies means many people have the same problem, which is where product ideas come from.
- How do you stop feeling ''guilt'' or miserable about not making as much as others?
Hello, I feel like im a pretty smart person and open minded, but when it comes to profits I feel somewhat depressed when I see others that have less or same amount of experience do much better than I do. I'm in…
96 replies43Check if it's worth building → - Rich uncle wants to help me to start a business but i don't know what...
I have an uncle who has multiple businesses. Hes already a millionaire and i guess hes bored. He wants to support me (i live in another country, hes outside of EU) to start something myself. I guess he wants a…
85 replies51Check if it's worth building → - How do I get the capital to start again?
Short back story. I've made 999silver jewelry for years. Had a good two year run with an online business that took off , personal stuff made my brain broken & I let everything crumble. Had to sell my equipment and all…
53 replies63Check if it's worth building → - How do you handle follow-ups when a prospect goes silent after you've done a lot of work for them?
I run Ironfin, a small studio that builds photorealistic 3D visualizations, drone photogrammetry, and VR training environments for mining and infrastructure. It's specialized, high-effort work. We don't operate on…
50 replies41Check if it's worth building → - How do you manage an experienced employee who constantly tries to prove they know more than the manager?
How do you handle someone who has more years of experience, but never wanted a leadership role until recently? They’re knowledgeable and capable, but they tend to take over, try to do everything themselves, and…
46 replies24Check if it's worth building → - How do you delegate work you’re used to doing at a high level without micromanaging?
One thing I’ve found difficult as responsibilities grow is handing off work I’m used to doing myself. You want the same standard, but constantly checking behind someone defeats the purpose of delegating. For those…
45 replies34Check if it's worth building → - How do you save and reuse AI prompts?
I’ve noticed that once I find a prompt that works well, I often want to reuse it later with slightly different inputs. Curious how everyone handles this. Do you: \> use templates with placeholders? e.g. Hello…
38 replies9Check if it's worth building → - Has Ai been any help in conducting Market research?
I've seen on Instagram recently about Ai making market research easier. Back in the day you had to hold focus groups, and go through months of customer research before releasing your product or service ? Or are you…
38 replies25Check if it's worth building → - Advice wanted: How can I market my home-maintenance service in front of more homeowners?
Per the title, I have a home-maintenance service. I help people maintain their home and help with its continuous upkeep. Primarily interior, but light exterior as well. (I know this is not a new idea or business model)…
32 replies7Check if it's worth building → - How do you decide which market to focus on when everything looks like an option?
One thing I’ve found surprisingly difficult in international business is deciding what not to pursue u can look at a few countries and find reasons to go after each one. One has a bigger market, another is growing…
31 replies27Check if it's worth building → - Do most companies waste what their sales team is learning?
I think a lot of companies seriously underuse their sales team as a source of market research. Sales is talking to the market every day. They hear the same objections over and over, they know where prospects get…
29 replies11Check if it's worth building → - How do you forecast when the deals that close aren't the ones you thought would close? Or just properly forecast in general?
We moved off Notion onto Salesforce, so at least the data sits somewhere reasonable now. Appointments come in at a steady clip and two have verbally closed this week. Past that I'm blind. The two closing weren't the…
29 replies16Check if it's worth building → - Feeling stuck at this point, please give suggestions
I’m a web dev with 5+ yoe, working on contract right now and have been working with the same client since 1.5years now. Sometimes I feel scared as to what if I am laid off, based on current condition of tech industry…
28 replies22Check if it's worth building → - Please recommend an Alibaba supplier for good quality packaging for clothes
I've tried ordering plastic poly bags for clothing on Alibaba from two different suppliers, but the feel of the plastic is not exactly what I'm after. I'd like something that feels smooth and a bit thicker but have no…
17 replies8Check if it's worth building → - How do I create these AI cinema cartoon-style videos (like TJR)
Hey guys, does anyone know how to create these animations that TJR keeps posting? Is that higgsfield? I genuinely have no idea which model that is. Would appreciate any help! Thanks!
14 replies0Check if it's worth building →
Best time to post on r/Entrepreneur
For every hour of the week we checked what share of September 2026's posts reached the top quarter by upvotes (more than 29 upvotes). Small samples are smoothed so one lucky post can't top the list.
Best days
- Tuesday31% top
- Thursday30% top
- Friday27% top
Best hours (ET)
Not enough posts to say.
Best day + hour
Not enough posts to say.
“% top” = share of posts from that time that reached the top quarter. Across the whole month it's 25%, so anything well above that did better than average.
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Questions
What were the most popular r/Entrepreneur posts last month?
In September 2026 the top post was “What’s an employee appreciation gift people actually liked?” with 206 upvotes and 244 comments. The full top 25 is at the top of this page.
What is the best time to post on r/Entrepreneur?
There weren't enough posts per day and hour to say.
How often is this page updated?
Once a month, a few days after the month ends, so late upvotes are counted. This edition covers September 2026.
Where does the data come from?
Every public r/Entrepreneur post from the month (141 posts), read from a public Reddit archive. Removed, deleted and NSFW posts are left out.