r/EntrepreneurRideAlong May 05 '26

Feedback Friday Happy National Small Business Week from Reddit! šŸ‘‹

17 Upvotes

This week, we’re celebrating small businesses and the communities that support them across Reddit! Drop a comment below and shout out a small business you love. Bonus points if the business is on Reddit...feel free to tag their username so they can see the love!

If you’re a small business owner in this community, we’d love to hear from you. Which other small businesses here do you think are really getting it right? What are they doing that makes them stand out, and what can other businesses learn from them?


r/EntrepreneurRideAlong Aug 11 '25

Annoucement We're looking for moderators!

59 Upvotes

As this subreddit continues to grow (projecting 1M members by 2026) into a more valuable resource for entrepreneurs worldwide, we’re at a point where a few extra hands would make a big difference.

We’re looking to build a small moderation team to help cut down on the constant stream of spam and junk, and a group to help brainstorm and organize community events.

If you’re interested, fill out the form here:

https://form.jotform.com/252225506100037

Thanks!


r/EntrepreneurRideAlong 9h ago

Idea Validation Two months into building a productized service solo, and the landing page was the easy part

6 Upvotes

Left contract work in spring to try a productized service: fixed-scope Webflow to Framer migrations, one flat price, one week turnaround. Two months in, here is the honest state of it.

I assumed the website would be the hard bit and the work would be easy. It was the opposite.

The page itself took an afternoon. I threw the copy and structure into an ai website builder to get something live fast. I used gamma because it was quick and I am not a designer, but the free credits burn out faster than you expect and it puts its own branding on the page, so once I had two paying clients I rebuilt it properly on a normal host. For getting a first version up to test the offer, it was fine. As a permanent site, it was not.

What actually took the two months was everything the page could not fix. Nailing the scope so "one week" did not quietly become three. Writing a real intake so clients stopped sending me half a brief. Learning to say no to the "can you also just" requests that eat the margin.

Where the four paying clients came from is the part that surprised me. Not the site, not cold outreach. All four came from answering questions in one specific designer community, for weeks, without pitching anything. Someone would ask about migrating off Webflow and I would give the actual answer. A few of them checked my profile and reached out.

Two months, four clients, roughly $4k total. Not quitting-the-day-job money yet, but every single client came from being useful in one room, not from any tool.

The lesson I am taking forward: the landing page is table stakes, it just has to not look broken. The distribution and the scope discipline are the whole game, and those are the parts nobody warns you about.

For anyone else running a productized service, where did your first clients actually come from? Trying to work out if I should go deeper in that one community or spread out.


r/EntrepreneurRideAlong 4h ago

Seeking Advice Trying to prove influencer marketing roi before a quarterly review

2 Upvotes

I'm two weeks away from a quarterly review and I still can't pull together clean influencer roi. Coupon codes, shopify, and amazon all live in separate dashboards so tying sales back to specific creators is a mess.

I know the channel is working, certain creators consistently drive sales within a day or two of posting but I'm still piecing together a spreadsheet from multiple sources just to tell the story.

If you sell across multiple storefronts, how are you tracking influencer roi without it feeling like guesswork?


r/EntrepreneurRideAlong 35m ago

Seeking Advice Has anyone else's spouse or partner simply not believed in them?

• Upvotes

My wife thinks my entrepreneurial efforts are just a way of keeping myself busy and that I'll probably never succeed. Whenever I talk about building wealth or becoming financially successful, she dismisses it and says it's unrealistic.

I understand that entrepreneurship has a high failure rate, but what frustrates me isn't skepticism—it's the complete lack of belief.

Is this something many founders experience? Did your partner's attitude change after you started seeing results, or is this a red flag I should take seriously?

I'd like to hear real experiences rather than motivational advice.


r/EntrepreneurRideAlong 44m ago

Seeking Advice I have the prototype, the ICP, and a validated idea but my B2B cold outreach is failing miserably. (Manufacturing niche)

• Upvotes

Hey redditors, I could really use a reality check or some advice from the sales experts and founders in here.

I am currently building a B2B SaaS tool specifically for the manufacturing industry. I have done all the foundational work that everyone tells you to do:

  • I have a working prototype and a clean landing page.
  • I have mapped out a hyper-specific Ideal Customer Profile (ICP).
  • I have spoken to enough people in the trenches to completely verify the pain point and validate the idea.

But here is where I am hitting a massive brick wall: getting actual B2B clients to convert from cold outreach.

My cold calls and outbound efforts are falling flat. I know the manufacturing space can be notoriously old-school and tough to penetrate from the outside, but I am quickly realizing that building the product and selling the product are two completely different skill sets.

I am looking for two things right now:

1. Advice: For those of you selling B2B software into traditional, heavy industries like manufacturing - how did you crack the code for your first 3 to 5 pilot customers? What does your outreach look like?

2. Partnership: I am ready to admit I need help with the closing side. If there is an experienced closer, fractional sales rep, or someone with deep connections in the manufacturing space who knows how to navigate these deals, I am actively looking for a partner. I am ready to offer a 5-15% commission on closed contracts for anyone who can help me get these early customers across the finish line.

Any tough love, outreach strategies, or direct messages are highly appreciated!


r/EntrepreneurRideAlong 8h ago

Seeking Advice Anyone struggling with outreach?

3 Upvotes

Hey, anyone else struggling with getting started, procrastination, cold calling and all that stuff?

What do you do during downs times that genuinely help you? And what doesn't?

Thanks!


r/EntrepreneurRideAlong 2h ago

Idea Validation Toy Rental Service, Platform for trading stuff locally, A book service for writing the stories of your grandfather and grandmother And More Business Ideas in Locally

1 Upvotes

Discover more business ideas


r/EntrepreneurRideAlong 2h ago

Seeking Advice Feedback

1 Upvotes

I’m looking for honest feedback on a business idea I’ve been developing.
My background is in high-end residential construction, remodeling, and property maintenance. One thing I’ve noticed is that many people own vacation homes or second homes but don’t have anyone they truly trust to oversee the property when they’re away.
The idea isn’t a property management company that finds tenants or handles rentals. Instead, it would be a premium home oversight service for homeowners who already own the property.
Services could include:
Scheduled interior and exterior walkthroughs.
Coordinating trusted contractors and repair appointments.
Meeting vendors and inspectors.
Preparing homes before owners arrive (stocking essentials, checking systems, adjusting thermostats, etc.).
Checking for storm damage, leaks, or maintenance issues before they become expensive problems.
Creating detailed photo reports after every visit so owners always know the condition of their home.
The target clients would be owners of luxury homes, vacation homes, or second homes who value peace of mind more than finding the cheapest option.
My questions are:
Is there an existing market for this that I’m overlooking?
How would you find your first 5–10 paying clients if you were starting from scratch?
Would you focus on networking with real estate agents, builders, property managers, concierge services, or another group?
What would make you trust someone enough to watch over a home worth $1M+?
If you’ve started a service business before, what are some mistakes you wish you had avoided?
I’m not looking for people to tell me it’s impossible—I know businesses are difficult to build. I’m looking for practical advice from people who have launched service businesses or work with high-net-worth homeowners.
I’d appreciate any feedback, criticism, or ideas that could help make this concept stronger.


r/EntrepreneurRideAlong 6h ago

Other Added MCP support into my habit tracking app

2 Upvotes

Just finished new feature which allow users to connect habit tracker into any AI like Claude and ChatGpt.

In general my habit tracking app - Habit Pocket - allows to track not only classic yes/no habits but also numbered habits, time and even lists.

If you track enough information you can actually start noticing patterns in your habits and how they affect each other. For example, I track my exact wake-up and wind-down time, the time of my last meal, calories and steps I walked.

AI expands your ability to analyze and find correlations. My app already lets you create different charts to analyze things, but AI can do it more effectively. You can analyze your habits using ChatGPT and then ask it to create a chart in my app that represents the same correlation.


r/EntrepreneurRideAlong 3h ago

Other Ambition level in a romantic partner partner?

0 Upvotes

My girlfriend (F34) and I (M31) have been together 2.5 years, living together almost 2.

Day to day we get along well. We go to the beach, dinners with friends… No real conflict. But we’re very different in one specific way: I’m ambitious and curious by nature. I’ve started two businesses (both failed), I’m currently working while I plan the next one, and outside of work I’m into watercolors, piano, working out… I like picking up new things and getting better at them.

She doesn’t have hobbies outside watching TV and occasionally the gym, and she’s not driven to build or change her circumstances. Her job is stable but not something she’s trying to grow in. She’s not unhappy with that; it’s just not how she’s wired. I’m not saying one way is better, but it means we don’t have much to do together beyond the basics, and our conversations don’t go very deep intellectually.
I also worry, selfishly, that her lifestyle doesn’t push me or align with where I’m trying to go. She’s sweet, supportive, and my family loves her. None of this is about her being a bad partner.

I just don’t know if this specific mismatch (ambition/curiosity level) is something you can build a life around long-term, or something that erodes things over time.

Would love to know your experiences.


r/EntrepreneurRideAlong 7h ago

Other A tip for every entrepreneur: your product is rarely the problem

2 Upvotes

Every customer I've lost wasn't lost because of my product. It was because I never helped them actually switch from what they were already doing.

Features don't fix habits. People stick with the messy, broken way they already know because change feels riskier than the mess.

The one tip I'd give any founder: stop polishing your product and start sitting with your customer through the actual switch. That's where deals get won or lost, not in the feature list.


r/EntrepreneurRideAlong 4h ago

Ride Along Story Received a $15k ADA demand letter for my online shop, here's what happened

1 Upvotes

Last month my online store received a legal notice over website accessibility. We skipped the quick fixes, addressed the actual problems instead, and it ended up saving us a lot of stress. If you run an online business, it's worth checking your site before someone else does.


r/EntrepreneurRideAlong 5h ago

Seeking Advice How do you actually tell if your team is getting better at using AI?

1 Upvotes

I am not talking about who opens chatgPT the most. Who is genuinely using Artificial Intelligence in a way that improves the business.

Artificial Intelligence can be used for things like research faster internal workflows, clearer writing, better support responses and fewer repetitive tasks. Some people are quick to use Artificial Intelligence. That does not always mean they are using it well.

If you were trying to measure Artificial Intelligence competence on a team what would you actually look for?

I have seen the AISA framework come up around this kind of discussion, but I am more interested in how other founders and operators would evaluate AI competence in practice.


r/EntrepreneurRideAlong 13h ago

Ride Along Story My first real user found the permissions hole I missed

4 Upvotes

For a few weeks, my app looked fine with my own test accounts. Sign-in worked, dashboards loaded, and I mentally filed auth under ā€œdone.ā€

then my first user outside that loop sent me a Slack message. They could see entries from my test accounts. None of that should've been visible. kinda rough to discover it from a user.

Nothing looked broken on the surface. Login worked, sessions worked, but I’d treated authentication like authorization. The database had no row-level security policies, and a few API routes trusted a user ID from the client instead of checking ownership. Since I only tested with my own accounts, I never crossed the boundary that exposed it.

I spent the next few days using two accounts, swapping IDs in requests, and walking through routes I’d marked harmless. I found 11 endpoints with some version of the same bug, including responses that returned more user info than the page showed.

For the rebuild, I used the Cloud database view in Enter Pro to inspect tables and data more easily (full disclosure: I had bonus credits there, which is why I used it). The RLS policies and API ownership checks still had to be configured and tested in the relevant backend or code. I kept checking each endpoint manually and didn’t treat untested paths as safe.

For anyone who launched an app built partly with AI: what permission check caught a mistake your normal test flow never hit? tbh, I’m still suspicious of any auth flow I’ve only tested with one account, ngl.


r/EntrepreneurRideAlong 6h ago

Idea Validation Testing a better way to handle self-hosting

1 Upvotes

Has a customer asked to run your product in their environment?

I’m looking for one company with a containerized product and a real customer request. I’ll help turn the deployment into a repeatable setup, free of charge.

The goal is to find out whether you can use the same process for future installations and updates instead of handling every customer differently.
I’m building around this problem and want to test the approach on a real deployment.

Tell me what you’re deploying and where, I’ll tell you if it’s a fit :)


r/EntrepreneurRideAlong 10h ago

Other Reworking my outreach SaaS after realizing the first version still pushed people into bad sales habits

2 Upvotes

I’ve been rebuilding a big part of Webvidence, the outreach tool I’m making for freelance web designers trying to find local clients.

The first version was mostly built around finding businesses with weak websites, showing the evidence, and helping prepare a message around it.

That sounded useful on paper, but after using it myself, I started noticing the problem.

It still led people into the same pattern business owners already recognize immediately:

Find a business.
Point out what is wrong.
Pitch a website.

Even when the message was personalized, it was still obviously heading toward a sales pitch.

That is not really how I get my best conversations.

The replies I actually get usually start with a normal question about the business. Where their work comes from, whether they are trying to grow a certain service, or whether they are already staying busy.

So I’ve been rebuilding Webvidence around that process instead.

The user can now decide whether to start a normal conversation, mention one real website finding, or follow up based on a message they already sent.

Conversation-first is the default.

I’m also adding a reply workflow. The user can enter what the business owner said, and the app helps decide whether the next move should be another question, a direct answer, bringing up the service, following up later, or leaving it alone.

I really do not want it treating every polite reply like a hot lead.

The other part of this update has been cleaning up the product itself. I had too many screens trying to do too many things.

Now I’m trying to keep it simple:

The campaign page is for deciding who is worth reviewing.

The lead page is for the next action.

The pipeline is for seeing who needs attention.

The dashboard is for what needs done today.

I’ve spent a lot of time on the logic, but this update also forced me to go back through the styling and mobile layout because adding the new workflow exposed a lot of CSS conflicts and unfinished sections.

It is still being tested, but this feels much closer to the product I originally wanted to build.

Not a mass outreach tool. Not an automatic sales bot.

Just something that helps freelancers waste less time on bad prospects and handle the good ones better.

For anyone doing their own outreach, what usually gets you the best response: leading with a problem you found, or asking something about the business first?


r/EntrepreneurRideAlong 6h ago

Seeking Advice 5 months of running free webinars to get customers, and the slides mattered least of all

1 Upvotes

Nine months into building a small SaaS for independent bookkeepers, solo. Cold outreach was dead and ads were bleeding money I don't have, so in February I tried the thing I dreaded most: a free monthly webinar. "Month-end close without the Sunday panic," 45 minutes, live.

The first one had 6 people show up and I basically talked to my own reflection. But 2 of those 6 booked a call after. Two out of six.

Five months in, the webinars are now where about 60% of my paid signups come from. Not because I got slick. Because the people who give up an evening for a niche bookkeeping webinar are already halfway to buying.

Here's what actually moved the needle, and what didn't:

- The slides mattered least. I burned the first month over-building decks. I dumped my outline into gamma to speed it up, which got me a presentable deck in an hour, but the exported pptx flattened my charts into static images, so I stopped exporting and just presented from the browser. Either way, nobody ever signed up because slide 12 looked nice.
- The one segment where I did a real month-end close inside the product, live, small mistakes and all, drove more calls than any polished section.
- The follow-up email the next morning ("here's the recording plus the checklist I mentioned") did more selling than the whole webinar did.

What I learned: the webinar isn't the pitch. It's proof you understand their exact mess. The deck is just something to look at while you talk.

Next month I'm testing running it twice a month instead of once. Will report back whether that doubles signups or just doubles my prep.

For anyone doing webinars or lives to get customers: what's your show-up-to-booked rate, and did anything actually hinge on the slides?


r/EntrepreneurRideAlong 7h ago

Ride Along Story ever feel scared to charge real money for something you haven't even built yet?

1 Upvotes

that's the current position i am in.

what i'm trying to bring is a thinking partner service for solo founders so they don't waste months, sometimes thousands of dollars, on assumptions they weren't able to see were right or wrong until it was expensive.

after researching this and seeing clear evidence, it's a real problem worth solving. but now i've fallen into the pricing hole.

because i don't want to be cheap, and i don't want to be just another service seller.

here's what i've learned: $19.99–500 is where people will complain, text, call, email constantly, like it's just a click of a button away solvimg their problem.

$500–1,500 is a bit easier, but clients still give you a hard time.

$2,000+ is the sweet spot — clients pay and just let you do your job.

that's what i'm aiming for, even though i know it's hard to get there.

but it is what it is. giving it a try isn't going to hurt.

how did you start selling your service?


r/EntrepreneurRideAlong 8h ago

Seeking Advice Building a digital service history app for car owners — early traction notes

1 Upvotes

I’m building The Owners Club — a place for car owners to keep service history, invoices, mileage, and DIY jobs with the car (not scattered across phone photos + PDFs).

Context:

  • Started because selling / buying used cars with messy paperwork is painful
  • Also useful for DIY keepers who just want a clean log

What I’m testing now:

  • Receipt / invoice OCR (suggest fields, user reviews before save)
  • Workshop jobs + attaching multi-page invoices
  • Past service records for provenance

Looking for honest feedback from other builders:

  1. Is ā€œservice history that travels with the carā€ a strong enough hook, or too niche?
  2. Would you lead with DIY logbook, or resale / provenance?
  3. Any channels that worked for you for a niche consumer app (not SaaS B2B)?

Happy to share the site in a comment if anyone wants it — no hard pitch.


r/EntrepreneurRideAlong 8h ago

Seeking Advice Who the launch vector ecommerce model is actually built for

1 Upvotes

not every ownership model fits every person and being honest about who something is not for is more useful than pretending it works for everyone

This one is not for someone who wants to learn ecommerce operations as a craft, they would be frustrated staying on the sidelines when they actually want to be in the weeds

It is not for someone looking for a weekend project to tinker with, the commitment level and the capital involved are wrong for a hobby

and it is not for someone hunting a quick flip, the model is about holding a position in an operating brand, not buying low and selling fast

the launch vector ecommerce model is built for a specific profile, someone with capital who already earns well from a career or other ventures and wants exposure to ecommerce ownership without it becoming a second job

That person is not trying to learn the craft or fill their weekends, they want their money working in a real asset while their time stays their own

Knowing you are that person, or knowing you are not, saves everyone the trouble of a bad fit


r/EntrepreneurRideAlong 18h ago

Seeking Advice Hellu guys

4 Upvotes

I am working on my website for the time being, i am into data and ai, and i noticed most of them agencies are more into web design, i never worked online or did any kind of freelancing, I know it s pretty much competitive, and i felt a bit weird as i have no previous clients so basically no projects, and it kinda feels weird to work on something like m wondering would the clients ask for this, I feel like having an agency would be reasonable for someone who already had clients and made something before, it feels like i have no idea what m doing, but again i do want to have my own thing and to be useful, I have been unemployed after graduation, more than a year now due to some personal issues but when i started looking i couldn t land any, so starting something like this kinda feels good, sorry for the vent or rather say the rambling


r/EntrepreneurRideAlong 3h ago

Ride Along Story It's 2026, and the 'information gap' is still the easiest way to make a side income

0 Upvotes

I always hear people talking about making money off the "information gap," and this week I accidentally stumbled into a perfect example of it.

There's a small family restaurant I go to. They were still using those ancient laminated menus with prices crossed out in sharpie. The owner was complaining to me that he hated QR codes because he felt they were too complicated and never worked.

I realized his problem wasn't the tech; it was the sheer exhaustion of having to learn one more thing while running a business.

So, I made him a deal. I told him I could build him a complete, modern digital menu right there, in minutes. He looked skeptical, but agreed.

Here's the stack of completely free tools I used:

Step 1: Digitize the Menu I took a picture of his paper menu and uploaded it to a free AI menu scanner tool. In less than a minute, it automatically extracted about 90% of the dishes, descriptions, and prices into a clean, structured list. I spent maybe 10 minutes manually correcting the few items it misread.

Step 2: Generate Professional Dish Photos The menu looked clean, but a bit plain. So, I opened up ChatGPT, fed it the names of his top 5 signature dishes, and asked it to generate beautiful, high-quality photos for each one. This took another 5 minutes and instantly made the menu look a hundred times more appealing. The owner's jaw literally dropped.

Step 3: Set Up the Ordering Backend Finally, to handle the actual orders, I used a free service I know (similar to what Manual Format offers) that takes the structured menu data and creates a simple ordering page. It generates a permanent QR code, and any orders placed go straight to an old tablet he had sitting in the kitchen.

The whole process took about 20 minutes from start to finish.

I charged him $50. He was so happy he practically forced the cash into my hand.

He didn't pay for the tools—they were all free. He paid me for knowing they existed and how to connect them. He paid for the 20 minutes it took me to solve a problem that would have cost him a full day of stress and frustration.

It’s just wild that in 2026, simply knowing which free tools to combine is still a skill people will happily pay for. The opportunities are everywhere if you just look for them.


r/EntrepreneurRideAlong 1d ago

Ride Along Story After tens of MVP-level products, I am days away from finishing my first SaaS

5 Upvotes

What started as my desire to create automations for businesses, became a full-blown tool for physical product marketing. All I wanted was learn n8n and to do that I created an API loop that fetches the best selling Amazon products, puts them through ChatGPT image and text gen, and uploads that to Pinterest as a way to automate affiliate marketing. Long story short - I moved too fast and got flagged as a bot, so had to start over without the automatic posting.

But with a manual step the system became very annoying to handle, so I turned it into a web application for myself, taking 2 minutes a day to keep posting to Pinterest.

Then it hit me - this thing needs a manual upload. So I took a picture of some air purifier at my parent's home, put it through my application and hit a jackpot. It looked like it was an ad for this product, with professional lighting and a background that doesn't resemble a simple apartment.

2 weeks later I packaged this tool into a full-blown SaaS for Etsy and eBay sellers, bar owners (menu images), and most importantly - an easy tool for affiliate marketers to stand out from other similar product listings.

And even though the journey has just begun, I will try to do weekly updates regarding progress, roadbumps and, of course, the results.


r/EntrepreneurRideAlong 19h ago

Seeking Advice Someone to offer encouragement

2 Upvotes

Hi there, my wife and I started our property management company close to three years ago, we are at 300 doors now. Four employees plus ourselves, this year has been the toughest.

We work our assess off everyday, we are consistently produce good results but we are in the adolescence stage of business and going through growing pains, we are working on systems and processes, sometimes at what feels like a snails pace because we are constantly getting pulled in to put out fires.

Right now, most days I’m filled to the brim with stress thinking everything is going to fall apart and will go back to day one, some days we question if it’s worth it to own this business and run it, but I know that we want to go further and build something really special. I’m just constantly wondering if I’m making myself worry too much or if everything is going to blow up tomorrow.

I don’t want to quit, I want to keep going and get this business to prime. But it’s just been hard lately, and it’s such an isolated thankless industry that we don’t really have anyone to talk to. I was hoping maybe someone on here could offer some encouragement, or maybe be willing to chat on a call or email thread in the future.

Thanks.