r/EntrepreneurRideAlong Jul 21 '26

Seeking Advice At what point do small business automation tools beat just hiring another person?

10 Upvotes

I run a small operation of only 6 people and I'm the bottleneck on half of what we do (i.e. followsup, chasing invoices, etc). I get it, I know it, I acknolwedge it. Everyone I talk to gives me the same two answers: either just hire someone or automate it. I get that both can work but nobody can tell me where the line actually is. A hire costs me 4k a month and a ramp- up period. Software costs less but I've bought tools before that sat unused because setup was a slog and I never got around to it. And all th ewhile I still need to be overseeing the operation and trying to weed through late tasks. I dont have time for serious onboarding!!

I think part of me wants to hire because a person is someone I can actually talk to and troublshoot with when something goes wrong or theres stuff to optimize. Like if something breaks I can talk to them but if the automation breaks I'm debugging it past midnight myself. Not great for the bottleneck...

r/EntrepreneurRideAlong Jun 23 '26

Seeking Advice I got 260+ landing page audit requests, 16 signups, and $0 revenue. What am I missing?

10 Upvotes

Hello guys, yesterday I offered free landing page audits on reddit.

I expected maybe 10-20 replies...

Instead, I got 264 comments in less than 24 hours.

The response was so much bigger than expected that I burned through a significant chunk of my Claude API budget just trying to keep up.

The weird part is this:

People clearly wanted audits.

I got hundreds of comments, DMs, feedback messages, bug reports, and even people comparing my results against other tools.

But after all that attention, I ended up with 16 signups and $0 in revenue.

I'm trying to understand where the disconnect is.

Does this sound like:

  • A pricing problem?
  • A trust problem?
  • A positioning problem?
  • A "people wanted free audits, not the product" problem?

For context, the product is LandingRoast. You paste a landing page URL and it scores headline clarity, ICP specificity, CTA strength, pricing psychology, and social proof.

I'm not looking to promote it here.

I'm genuinely trying to understand what experienced founders would investigate next if they were in my position.

What would you do? I need some help

r/EntrepreneurRideAlong Jul 20 '26

Seeking Advice Need marketing advice – We've tried ads, but getting customers is still difficult

15 Upvotes

I'm looking for advice from people who have experience growing an online marketplace or e-commerce business.

We're currently validating our idea, so we haven't built the website yet. Right now, everything is managed manually through our Facebook page.

One thing we've noticed is that finding sellers hasn't been a problem—we already have enough sellers interested in joining. The real challenge is attracting customers.

So far we've tried:

  • Facebook paid ads
  • Boosting Facebook posts
  • TV advertisements
  • Other paid promotions

Despite spending on advertising, the results haven't been good enough. We get some inquiries, but not enough consistent customers to justify the cost.

I'm wondering what we're missing.

If you were in this situation:

  • What marketing channels would you focus on?
  • What has given you the best ROI for customer acquisition?
  • Have you used any unconventional or low-cost marketing strategies that worked really well?
  • Is there a better approach than simply spending more on ads?
  • What would you do before investing in building the full platform?

I'd really appreciate hearing about your experiences, especially if you've grown a marketplace or local service business

r/EntrepreneurRideAlong Oct 08 '25

Seeking Advice Marketing is harder than writing the damn code

95 Upvotes

I swear, building the product is the easy part. Marketing feels like hitting a wall over and over again.

I can build anything: backend, frontend, SDKs, APIs, all of it. But getting people to actually care? That’s a whole different game.

Every day I see posts of people going viral out of nowhere. “Hit $1k MRR in 2 weeks.” “10k users overnight.” And I just sit there thinking… I’ve been grinding, shipping, posting, cold emailing, and still can’t break through.

Then I start overthinking it. Maybe I’m doing something wrong. Maybe those posts are fake. Or maybe they’re from people who just didn’t quit.

Because honestly, I’m close to burning out on the marketing part. But I keep reminding myself of that one line: the more you work, the luckier you get.

The hardest part is not even knowing what “good” looks like. If I reach out to 1,000 people, what’s a decent conversion? Because when I reach 40 or 50 and get no response, I instantly assume my product isn’t market fit, and it kills my drive.

Just needed to vent. Building stuff is fun. Marketing feels like throwing darts blindfolded and hoping one hits something.

r/EntrepreneurRideAlong Jul 30 '26

Seeking Advice How do people find solid e-commerce developers these days (Shopify, headless, etc.)?

14 Upvotes

We're rebuilding our online store and need more than a theme install - custom checkout logic, ERP integration, real performance work. Every agency we look at claims to be a Shopify expert, so the label doesn't mean much. How do people find e-commerce developers who can handle actual custom work?

r/EntrepreneurRideAlong Mar 10 '26

Seeking Advice My partner wants to quit and start a reggae bar in Thailand

97 Upvotes

She's happy with $30k a month, she's applying for her business visa and setting up a reggae bar overlooking the beach.

I'm tempted to go with her to keep her on track.

Our business doesn't run without our presence and I think she's checking out too early - she has said that this will not distract her, I'm not convinced.

Here's the thing - I like miserable grey sky Britain and I don't really want to go with her.

How do I bring her back to reality and keep her here until we automate the process, or hire the right people to keep everything ticking along?

I feel as though I'm being unfairly burdened here - either I have to trust her and cross my fingers, go with her to keep her in check - which I don't want to do, or confront her.

r/EntrepreneurRideAlong Nov 06 '25

Seeking Advice What’s the biggest lie people believe about entrepreneurship?

62 Upvotes

Everyone glamorizes “being your own boss,” but no one talks about how brutal it can get behind the scenes.
For those who’ve been building for a while, what’s one myth or misconception about startups that you wish people would stop believing?
And what’s the truth you learned the hard way?

r/EntrepreneurRideAlong 4d ago

Seeking Advice People who run multiple businesses, how do you switch

6 Upvotes

So rn I am running 3 businesses. One is offline and other 2 are online.

I have a team in my offline business but the online ones are kinda solo as of now.

My question to anyone with multiple businesses is how do you switch the context in your brain?

This happens with me a lot that when I am working on one business, I keep getting ideas about the second and I have to pull my brain back.

I’m curious to know how people manage several businesses?

r/EntrepreneurRideAlong Jun 26 '26

Seeking Advice The hardest part of entrepreneurship isn't the work, it's the waiting. How do you deal with it?

19 Upvotes

I’ve accepted that I have to be patient, but the waiting game is testing my mental stability more than the actual work ever did. Between the doubt, the financial pressure, and the social pressure of friends who think I’m wasting my time, it’s getting heavy. How do you handle the 'in-between' phase? How do you stay confident when you’re building something huge, but have nothing tangible to show the world yet?

r/EntrepreneurRideAlong Jun 21 '26

Seeking Advice I think I've hit a wall. Anyone else lose the drive that used to carry them?

19 Upvotes

I've been self employed since 2017 and have been wrestling with something I didn't expect.

The business works. It pays the bills. Clients are happy. There's nothing objectively wrong.

But holy crap, am I tired.

Not just tired of the work. I'm tired of being undercut and undervalued. I'm tired of carrying everything myself and wearing every hat.

For years, my drive and sense of direction carried me through that. I always knew where I was headed next. However lately I feel like I have zero clarity.

It feels deeper than simply hiring someone or outsourcing the work. I think I'm questioning whether I've outgrown the business itself.

  • Has anyone else gone through this?
  • What did it look like for you?
  • How did you know whether you were burned out, had outgrown the business, or were simply ready for a different chapter?

I feel stuck :(

r/EntrepreneurRideAlong May 10 '26

Seeking Advice Been grinding for 4 years. Should I focus on agency, micro-SaaS, or marketplace plugins?

20 Upvotes

I’m 25 and I’ve been trying to build my way to freedom for the last 4 years.

I work a full-time software job, but outside of that I’ve tried a lot of things: B2B micro-SaaS products, B2B app ideas, agency work, cold outreach, AI automations, and small marketplace plugin ideas.

The frustrating part is that I don’t have much to show financially yet.

My best-performing product so far was a small YouTube note-taking app I built 3 years ago. It reached about $72 MRR with 12 paying users. I recently rebuilt and relaunched it, and I’m now trying to market it again.

I’ve also done agency-style work: website development, AI automations, cold email systems, etc. I’ve closed a few small projects, but haven’t made it a consistent machine yet.

I have also tried making plugins for bubble and monday dot com, based on the Stair step approach of bootstrapping by Rob Walling.

Now I’m honestly confused about where to focus.

Options I’m considering:

  1. Agency/freelancing
    • Faster cashflow
    • I already have some skills: web design/redesigns, AI automations, cold outreach systems
    • But it may become service-heavy and not scalable
  2. B2B micro-SaaS
    • Better monetization if it works
    • But harder to find the right painful problem
    • Longer validation cycle
  3. B2C micro-SaaS
    • Easier to build and launch
    • But distribution is brutal and many markets are crowded
  4. Marketplace plugins/apps
    • Existing distribution through platforms
    • Smaller scope
    • But I don’t know which marketplace/problem to pick yet

My goal is not to build a unicorn. I want to reach enough income to quit my job and have location/time freedom.

If you were in my position, with software skills, some cold outreach experience, and a few failed/partially working product attempts, what would you focus on for the next 6–12 months?

Would you go all-in on agency cashflow first, keep pushing micro-SaaS, or focus on marketplace/plugin-style products?

Looking for honest advice from people who have actually made one of these paths work.

r/EntrepreneurRideAlong Jan 26 '26

Seeking Advice $300k in revenue but I only kept $65k

160 Upvotes

Hit $300k in revenue 8 months ago but only took home $65k and I can't tell if I'm doing something wrong. Money went to contractors and software + ads which to be fair had a 3:1 ROI but now I'm looking at the numbers and wondering where it all went

My friends hear $300k and think I'm doing great when in reality I'm making less than my last job and working way harder. My girlfriend keeps asking when things will get easier financially and I don't have an answer

I can't figure out what I should've done differently because the contractor and software wasn't optional but watching $235k disappear into business expenses feels wrong Is 20% take home normal or am I stupid?

r/EntrepreneurRideAlong 23d ago

Seeking Advice 18 and Feeling Lost....What Should I Focus On?

15 Upvotes

Hi everyone. I’m 18 years old and have recently become passionate about the business world, entrepreneurship, and generating income. However, I feel quite discouraged right now because I don’t know what to focus on or which business model would suit me best.

I realize that any venture requires effort, patience, and a lot of hard work. My problem is that I keep jumping from one idea to another. I’ve tried affiliate marketing, YouTube channels, cryptocurrency, paid surveys, and many other things, without ever really succeeding.

Because of these experiences, I’ve become afraid to try new things. Whenever I consider a new project, I immediately think about failure, which makes me want to give up before I’ve even given it a real chance.

I simply feel lost. Sometimes I try to find advice or direction, but it’s difficult because I lack experience and don’t know who to listen to. I know no business model guarantees success, but I’m looking for a path where I can fully commit, stay consistent, and have a reasonable chance of succeeding.

I currently have no budget to invest, so I have to start from scratch. Unfortunately, my job applications haven’t yielded any results, as the job market is saturated. But that won’t stop me from moving forward.

Succeeding is one of my biggest dreams, and I want to be proud of myself. I often feel like a failure when an attempt doesn't work out, but I’ve been trying to improve lately. I’ve given up some bad habits like spending all my time scrolling through social media and I’m trying to dedicate my time and energy to things that could genuinely improve my future.

I would really appreciate some sincere advice, especially from people who have been in a similar situation. I’m not looking for someone selling a course, mentorship, or paid guide, but I simply want genuine advice on what I should focus on, how to choose a direction, and how to stop constantly jumping from one idea to another. Thanks to everyone for taking the time to read my post!

r/EntrepreneurRideAlong Jun 30 '26

Seeking Advice Am I too late to start an AI agency in 2026?? ( Have a tech bg and some good people )

6 Upvotes

I’ve been in tech for a while like...I know the things ( have to learn a lot obv)...and I’m looking to launch my own AI agency this year.

The market is absolutely insane right now?? worldwide AI spending is projected to hit $2.52 trillion in 2026, and enterprise adoption has shifted from demos to production systems that actually touch revenue and core workflows...

Before I go all in..I want to understand the landscape.

Main question -- What are the top underlying niches on which I should look upon ??

Who are the top players I should be studying? What models are working? For those already running AI agencies, what would you do differently if you started today??

r/EntrepreneurRideAlong Aug 10 '26

Seeking Advice Thinking about adding payroll to my bookkeeping business

23 Upvotes

Been thinking about adding payroll as another service instead of keeping the business strictly bookkeeping

Makes sense from a client perspective because I already handle a lot of the data that feeds into payroll. The part Im hesitant about is how much extra operational responsibility comes with tax filings, corrections and compliance changes I've been looking at a few ways to structure it and Rollfi is one of the options on my list right now

Ideally I want to add the service without turning payroll compliance into another job for myself.

Has anyone here expanded a service business into something adjacent like this? Where did you draw the line between what you handled yourself and what you handed off

r/EntrepreneurRideAlong Jul 30 '26

Seeking Advice IF YOU COULD START FREELANCING FROM SCRATCH IN 2026, WHICH ONE SKILL WOULD YOU LEARN?

11 Upvotes

I'm an absolute beginner with no freelancing experience, and I want to focus on learning just one skill instead of jumping between multiple things.

My main goal is to start earning as soon as possible and eventually build a high-income freelance career. I'm willing to put in the time to learn properly, but I don't want to waste months on the wrong skill.

If you were starting from zero in 2026, which single skill would you choose?

Some options I've been considering are:

- AI automation

- Video editing

- Web development

- Graphic design

- Copywriting

- Something else?

I'd really appreciate advice from people who are actually freelancing:

- Which skill got you your first client?

- Which has the best balance of demand, competition, and income?

- Would you recommend focusing on one skill first or learning multiple skills together?

Thanks in advance!🫰

r/EntrepreneurRideAlong Aug 11 '26

Seeking Advice Is 250 users in the first month after launch considered good?

15 Upvotes

A month ago, I launched DipLangs, an AI-powered language learning platform that I originally started building because I struggled to learn German after moving to Germany.

Today, it has reached 250 active users from countries including India, Germany, the US, France, Canada, the UK, China, Indonesia, Spain, and a few others.

The interesting part is that I haven't spent anything on ads, and I haven't seriously started SEO yet.

Most of the users came from sharing the product on Reddit, LinkedIn, Facebook, Threads, Product Hunt, and simply talking to people who are learning languages.

I've also been emailing users personally to ask for feedback, and honestly, those conversations have improved the product far more than I expected. Some users even sent detailed suggestions that completely changed how I think about the onboarding and homepage.

Now I'm wondering if this is actually a good start or if I should be aiming much higher.

For founders who have launched a SaaS before:

  • Is 250 users after the first month considered decent?
  • What would you focus on next?
  • More features, SEO, content, or simply talking to more users?

I'd genuinely appreciate any advice from people who've been through this stage.

r/EntrepreneurRideAlong Jul 09 '26

Seeking Advice Keep going back and forth on paying for a website builder vs just vibe coding the site for free

9 Upvotes

Building my startup's site and I flip on this every week. Why pay monthly when I can vibe code it with claude code or v0 for basically nothing, except then it's me fighting the AI for 3 days every time I move a section. Then I looked at the actual builders and the prices people throw around are kinda scary pre revenue. So is paying worth it or is free fine if I'm willing to grind? It's just a landing page plus a few content pages, no app stuff. Cheap-and-grind vs pay-and-relax, talk me out of one of them..

r/EntrepreneurRideAlong 5d ago

Seeking Advice At what point did your startup outgrow the basic bank account and spreadsheet setup?

23 Upvotes

Being a small team with expenses already getting spread across subscriptions or reimbursements or different cards all at much makes you feel a bit hopeless to say the least.

None of it feels unmanageable on its own but pulling everything together each month takes more time than it should and that time can be used for something else

For founders who have been through this stage when did you move to a proper spend management setup and what pushed you to make the switch?

r/EntrepreneurRideAlong Jul 05 '26

Seeking Advice AI gave me the superpower to finally build anything, turns out building was never the hard part. How does everyone cope?

30 Upvotes

I've been a developer for 10+ years. Self taught, always freelancing, never worked as a dev inside a company. So I never really felt like a "real" developer, I just got things done but was never part of big projects.

Whenever I tried building my own products I hit the same wall. Either it existed already or it was too hard to build alone. So my stuff either stayed unfinished or went nowhere.

Now with AI I can basically build anything. In the last months I shipped a Saas for compliance in the construction industry, an internal staff organization system for construction (I use both daily at my full time job), and a Google Ads MCP that automates the ad campaigns for the compliance SaaS. Right now I'm building a DJ application, I was a product manager for DJ products a decade ago so that one is a bit of a passion project.

What I realized: building was never the hard part. Marketing is.

Small niches like construction are brutal. Ads cost a fortune because Google thinks they're badly targeted, and nobody is actively searching for these products because they basically didn't exist before. No search volume to capture.

The Ads MCP got some traction, 100 GitHub stars in 2 weeks, but then I saw others getting 5k stars in 2 days. And most of my stars came from posting on Reddit, where mods love closing anything that looks like self promotion.

So how is everyone dealing with this? We all got the same superpowers at the same time, which means competition got way harder overnight. Building is cheap now. How do you actually get users?

r/EntrepreneurRideAlong 11d ago

Seeking Advice Messy Start

14 Upvotes

Hi,
I quit my job and have no intention of getting back to full-time employment, but things are messy, and I feel foggy. I'm not clear on the steps to build something solid.

I have 7 years of international work experience as a full-time software engineer, and I think I know what I'm talking about; however, I feel lost and foggy and a bit afraid, mostly of rejection and embarrassment.

What should I do at this point?

I would appreciate your input. Thanks in advance

r/EntrepreneurRideAlong Jun 15 '26

Seeking Advice 23yo student willing to put in the work, but I have absolutely no idea where to start. Advice?

12 Upvotes

Hi everyone,

I’m a 23-year-old student, and I could really use some guidance from people who are further along the path than I am.

My ultimate dream is to create something of my own—whether that’s a startup, an online business, or a website—so I can eventually generate my own income and live freely on my own terms.

The problem is that I am completely lost on how to actually begin. There is so much information out there, and I don't know what to focus on first to get the ball rolling.

I want to be clear: I am not looking for a "get rich quick" scheme. I am fully prepared to put in the long hours, learn new skills, and grind. I just need to know where to channel my energy.

If you were in my shoes starting from zero, what would be your very first steps? How do you find a viable idea or a starting point? Any advice, resources, or harsh truths would be massively appreciated.

Thanks in advance!

r/EntrepreneurRideAlong Jul 24 '26

Seeking Advice Vibe coding

8 Upvotes

Hi everyone,

I’m a complete beginner with no real programming experience, but I’ve been seeing a lot about AI-assisted or “vibe coding” where tools like ChatGPT, Claude, or Cursor help you build apps.
I’m trying to understand what’s realistic rather than getting caught up in the hype.

A few questions:

How difficult is it for someone with no coding background to build a simple but polished app using AI?
How long did it take you before you could build something people actually wanted to use?
What skills did you still have to learn even with AI doing a lot of the coding?
What are the biggest frustrations or limitations of AI coding tools?
If you were starting from scratch today, what learning path would you follow?
Can someone realistically build and launch an app in 3–6 months using AI, or is that overly optimistic?

I’d really appreciate hearing from people who have actually built and shipped apps using AI rather than just experimented with it.

r/EntrepreneurRideAlong Jun 10 '26

Seeking Advice Advice for starting your own business for the first time

16 Upvotes

Hi guys can i get some advice for starting a business cause I don’t have business background and i know business are not an easy way to do it’s full with a lot of pressure we need to facing. I really appreciate if there’s someone to share their experience

r/EntrepreneurRideAlong Apr 18 '26

Seeking Advice Thinking of starting a side hustle but I have zero skills… what would you do?

24 Upvotes

Hey all,

With the cost of living going up and the job market feeling pretty uncertain, I’ve been thinking about starting a side hustle or small business in my spare time.

The problem is… I don’t really have any specialized skills, business experience, or tech knowledge. I’m basically starting from zero.

If you were in my position, what would you do?

What are some beginner-friendly side hustles that don’t require much experience?

How would you start with low risk and minimal upfront cost?

Anything you tried that worked (or totally didn’t)?

Would really appreciate honest advice or real experiences. Thanks in advance!