What r/Entrepreneur keeps coming back to
Complaints raised here by more than one person. One-off posts are not included.
70 recurring problems · 228 threads read · read since September 2026 · Reddit
Raised more than once here
Most people first.
- 98How to stop letting accounting stress ruin my life?“My panic attacks peaked when I answered every Slack pings at 2 AM.”
- 62How to handle unexpected software subscription price hikes and slow support“We are paying for 23 separate software subscriptions right now, everything from accounting to project management to CRM to email marketing to analytics to internal communication to file storage to scheduling to customer support to payroll, and the total monthly spend across all of them is $4,100 which is almost $50,000 a year on software for a 12 person company.”
- 47how do I get my first client?“I would appreciate any suggestions on how I can reach potential prospect clients to pitch my services to.”
- 43How to handle the financial and identity drop after leaving a career“What has been insane is the lifestyle freefall.”
- 28How to handle clients who demand refunds and bully you“Finally I walked. I had enough. I realized he was a nightmare client and his expectations were ridiculous.”
- 28How to start a business with no industry experience“I am looking into medical supplier and really need help in getting my foot in. How do I and where do I get started? Any pointers to websites links or courses? Any current or former employee willing to mentor?”
- 27How to balance a corporate career with having kids“That depends on how you define successful. If I have to give up my family life, that is not something I would consider a success.”
- 23How to avoid chaotic seat scrambling at a reception“I think there’s a place in the market to perfect your seating plan.”
- 22Why is project management just doing admin and updating trackers?“spent two hours this week on an invoice formatting issue. two hours. on formatting.”
- 19Why isn't cold outreach booking any client meetings?“I've tried several different cold email approaches, but haven't had much success getting replies.”
- 18How to respond when a client says your rates are too high“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?”
- 16Should I register a business before making any money?“Rich uncle wants to help me to start a business but i don't know what...”
- 14How to figure out what product to sell online“The hardest part of starting my entrepreneurial journey is that I have limited skills and zero connections. I'm a software developer, and that's the only thing I know, so I have a hard time coming up with good ideas”
- 14How to handle running a business completely by yourself“burnout hit me about 18 months into running my own thing. i kept thinking i just needed to push through it, that it would get better once i hit the next milestone. it didn't.”
- 12Why do simple CRM automations get so complicated?“Chaining a bunch of agents together usually just creates an endless game of telephone where you spend more time fixing their weird handoffs than actually getting work done.”
- 12How do you manage money across multiple countries and currencies?“Customers paying from one country, suppliers in another, contractors somewhere else, then different currencies and accounts on top of that. None of it is individually that complicated, but once you’re dealing with all of it at the same time, it gets messy pretty fast.”
- 11How to quit a corporate job to start your own business“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.”
- 11Migrating an established online store to Shopify Plus“I want everyone together on Nuke Nomad, but even after telling people about the new platform, the move has been slow.”
- 9Why are restaurant and cafe startup costs so high?“Dont overcapitalise, i spent like 300k building a very fancy restaurant about 1.5hrs away from Sydney, Australia......i would of been better off to use that 300k to rent a little tiny whole in the wall shop in Sydney CBD and whack a 20k coffee machine in it.”
- 9New hire interviewed well but can't do the job“A bad hire becomes obvious around week two or three, but without a checkpoint you second-guess yourself into month four.”
What this forum worries about more than the rest
How much more often a topic shows up here than across every forum we read.
ideation85.6×difficult clients85.6×cold email85.6×venture capital85.6×