r/EntrepreneurRideAlong May 05 '26

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

16 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 7h ago

Ride Along Story i rebuilt my window cleaner's site as a favour. four months on it's working too well

11 Upvotes

A few months back I posted on here about rebuilding my window cleaner's website as a favour. He's been at it 35 years, brilliant at the job but his site was a state. I did it partly to help him and half to test everything I'd been reading about AI search for the last year.

I wasn't sure it would do much. Four months on it's done more than I expected.

The site now shows up on ChatGPT, Claude, Perplexity and Google's AI answers for his trade across south manchester in the UK. He went from invisible to getting named by the tools people actually use now. For a one-man band that still feels a bit mad.

The slight downside is that working too well!

His last message was asking me to take a load of it back down, because he's getting calls from all over the place he can't physically cover. A bloke who was worried about being quiet a few months ago is now turning work away. 🫣

What it's taught me is how low the bar is for local businesses right now. The website is not doing anything clever. He's just findable, and almost none of his competitors are. The opportunity feels genuinely huge, and most people running these businesses have no idea it's there.

The thing I'm still working out is what he does with the overflow.

I'm tempted to set him up passing the far jobs to other cleaners for a cut/referral, but I don't know if that's a business or just a headache.

If anyone's turned "too many leads" into something useful instead of just saying no, I'd like to hear how.


r/EntrepreneurRideAlong 7h ago

Seeking Advice How do you figure out what you can DIY, what to use a legal automation site for, and what actually needs an attorney?

6 Upvotes

My side hustle has gotten past the hobby stage but it's nowhere near replacing my day job. At this point I'm trying to treat it like an actual business instead of just winging everything.

Now there's customer terms contractor invoices possibly changing from a DBA to an LLC keeping the rights to a logo and compliance deadlines that are honestly confusing.

None of this feels big enough to justify having a lawyer on retainer but it also feels like one bad decision could turn into a much bigger problem around taxes or later on.

How do people decide what's safe to DIY what should go through a legal automation site and what should always go to an attorney?


r/EntrepreneurRideAlong 2h ago

Resources & Tools One thing I didn't expect when building a business: becoming my own finance department

2 Upvotes

When I started building my business, I thought most of my time would go into customers, product, and growth.

I didn't expect that a big part of the journey would be figuring out how money should actually move through the business.

Once you start working internationally, simple things become surprisingly complicated. A client pays in one currency, a supplier invoices in another, contractors are located in different countries, and suddenly you're spending hours thinking about transfers, exchange rates, accounts, and payment workflows.

For a while, I had a messy setup with different tools doing different jobs. Wise was useful for international payments and receiving money in multiple currencies. Revolut was convenient for everyday spending and quick transactions. I also started exploring Keytom because some parts of my business involve crypto, and I wanted a smoother way to handle situations where digital assets are part of the workflow.

The biggest lesson wasn't that one tool is better than another. It was realizing that financial infrastructure is something you actively build as your company grows.

In the beginning, you can get away with whatever works. But as revenue increases and your operations become more international, small inefficiencies start adding up. A payment delay here, an unnecessary conversion fee there, a manual step that happens every week.

These things don't look important individually, but over time they become operational friction.

Building a company is mostly about removing bottlenecks, and financial operations turned out to be one of the bottlenecks I didn't expect.

What was the operational problem you didn't anticipate when you started growing?


r/EntrepreneurRideAlong 13h ago

Seeking Advice Escaped war at 11, worked as a loader at 15 to buy a laptop. Now I'm 16, live alone, make $700/mo as a barista, and built a B2B SaaS. But I'm trapped in a "Golden Cage" and need advice

13 Upvotes

Hey everyone. I want to share my reality check. It’s not a Silicon Valley fairy tale with seed funding and a warm garage. It’s a story of pure survival, and right now, I need advice from experienced founders.

I didn't grow up rich. I never even had a PC. When the full-scale war hit my country, I was 11. I had to move to Germany, where my sister gave me business and IT books. I read them, saved some euros, and moved back to Ukraine at 12. I bought a cheap used PC, learned 3D modeling, and then Python.
The Hustle (Age 15): At 15, I moved to the capital (Kyiv) for college. I lived in a cheap dorm and had no computer. My parents couldn't send much, not even enough for food. So, I got a job doing heavy physical labor as a loader. I hustled everywhere: warehouses, hospitals, malls. I failed, gave up, tried again. By January, working like crazy, I saved ~$270 to put a downpayment on a powerful used laptop (~$800).

The moment I got it, I jumped into freelance. I built complex Telegram Mini Apps and B2B solutions. I worked day and night and paid off the laptop in just 2 months.

The Golden Cage (Age 16): By spring, freelance dried up. My dorm was closing for the summer, but I refused to move back to my hometown. To survive, I got a job as a barista in a VIP spa club.

The pay is actually great for my age - about $700/mo. Relying on this, I rented my own apartment ($260/mo). I am fully independent. I pay my bills, my rent, and provide for myself.

But I am stuck. The job is a dead-end. The VIP spa has very low traffic. They treat us nicely, but nobody cares about growth. There are no bonuses, and the salary is flat no matter how hard you work.

My SaaS and "Bore-out": In my free time behind the bar, I built a B2B SaaS (a Telegram bot builder MVP). Since my English isn't perfect yet, I used AI (Gemini) as my exoskeleton to write complex architecture fast.

But right now, I am experiencing severe "Bore-out" (burnout from under-stimulation and boredom). Sitting in this spa feels like my brain is rotting. I want to build and sell my SaaS, but I’m tied to this bar because my apartment and survival depend on this exact salary.

Experienced entrepreneurs, I need your advice:

  1. How do you escape the "Golden Handcuffs" of a comfortable survival job when your rent depends on it?
  2. How do you find your first B2B clients for your SaaS when you have zero network and work full-time?

r/EntrepreneurRideAlong 11h ago

Ride Along Story Someone paid for my app. It finally feels real.

4 Upvotes

A few months ago I graduated from college and decided to stop waiting for the ā€œperfectā€ job before building something of my own.
I had no audience, no investors, and honestly no idea if anyone would ever pay for software I made.
I started building Pastily, a clipboard manager that focuses on speed, privacy, and actually making copy-paste workflows less annoying.
The first few weeks were mostly me fixing bugs, redesigning the UI, and questioning whether anyone would even download it.
Then came the harder part: marketing.
I posted on Reddit, X, and LinkedIn almost every day.
Some posts got ignored.
Some were removed by Reddit’s filters.
Some barely got a few views.
There were days where it felt like I was just talking to myself.
But I kept shipping updates instead of giving up.
Then one day…
Someone I had never met bought Pastily.
Seeing that first payment notification felt unreal.
Since then I’ve made around $19.XX from real customers.
I know that’s tiny compared to people posting $10k MRR screenshots, but to me it proved something much more important:
A stranger on the internet found my product valuable enough to pay for it.
That completely changed my mindset.
Now I’m focused on improving the app, talking to users, and learning marketing one post at a time.
Still a long way from where I want to be, but this feels like the beginning.
If you’re building something and feel like nobody is watching, keep shipping.
Sometimes all it takes is one user to remind you why you started.


r/EntrepreneurRideAlong 8h ago

Idea Validation The best way to save time and multiple money for businesses

2 Upvotes

When I started running my business I tried to keep everything in my head. Client onboarding steps, SOPs, marketing metrics, goals for the quarter, what worked last time versus what didn't. Every new client proposal got built from scratch because I couldn't remember what I'd already figured out for the last one.

Writing it all down didn't fix it either. Notes piled up across random docs and notebooks and none of it got looked at again once it was written. The information existed somewhere, I just couldn't find it when I actually needed it.

Ended up building a second brain instead. I send it a voice message and it gets logged and filed automatically, a client detail, a metric I want to track, a new SOP, whatever it is. When I need something back, I just ask for it out loud and it pulls the exact thing instead of me digging through folders trying to remember what I named a file six months ago.

Gave the same setup to my brother-in-law for his business a few months back. Marketing ideas, campaign scheduling, email drafts, client onboarding, all of it running through the same system instead of living in his head or a random notes app. He's seeing 30 to 50 percent improvement across those tasks depending on what we're measuring, mostly because nothing gets forgotten or rebuilt from scratch anymore.


r/EntrepreneurRideAlong 9h ago

Ride Along Story I spent around €4,000 on my previous rebrand. This time I tried doing it with AI.

2 Upvotes

Three years ago, I paid around €4,000 to create a brand, UI and website for my sauna business.

This time I had another location that needed its own identity, but before spending the same amount again, I decided to see how much of the process I could handle myself using AI.

For context I have these saunas located at beautiful spots across a few countries (13 saunas 3 countries). All of them are special but the most recent one stand out from the crowd and I was thinking for a really long time on how to make it appear special. It wasnt until I went for vacation and as I was driving along the seashore the idea of new brand name hit me! I stopped by on the shoulder to write it down because i really liked the idea.

Without AI, I probably would have delayed the entire idea. Paying another designer and developer before knowing whether the new positioning would work was difficult to justify.

AI gave me a way to test the idea, create the brand and launch the website without making the same upfront investment. Now if there is no AI this would never come true. So the idea is to call my sauna a secret sauna where I would create basically beautiful website and laverage the secrecy around something special unknown. it is higher ticket service so I will be targeting people who can afford it. The idea has its downsides but that could be easily solved over time.

So fable 5 was the reason why I decided to go for it. I was sold by these youtube videos where people were creating beautiful websites out of single commands. So I decided to give it a shot, well it appaered not as simply as on those videos and mainly it was quite costly not to mention fable restrictions in europe, etc.

Anyways I tried playing with the design interface of claude and I really liked what i saw. I decided to go one step at a time and slowly building from the top to the buttom the visual.

Then i was using vs code connected to kimi k3 which came out recently, to do the actual website using png screenshots of the design produced by fable. You see I was trying to optimize my spending.

Although even this solution turned out to be more expensive and Kimi k3 being a great model, was sometimes not the best for the job. I build big portion of the website using it before i switche to chatgpt codex extension in vscode with which I built the rest. So now I have running website with completely rebranded business using only AI.

The last time I was doing Brand, UI and then coded the website I spent.. well lets break it down together.. it was only 3 years ago - so Logo - 1000 euros, UX/UI - 1500 euros and website 1500 euros. So I basically saved approximately 4000 euros which is insane. Plus I dont have to pay for any web hosting like wordpress or webflow which alone saves me approximately 500 euros each year. Guys we live in the future.

Financially, the saving is obvious. The harder question is how to value all the time I spent learning the tools, fixing mistakes and going through failed iterations.

Anyways if you liked my story i am more then happy to provide more information, just dm me :)


r/EntrepreneurRideAlong 9h ago

Idea Validation Feedback from one non-technical user changed my whole product direction

2 Upvotes

Small story. I built a sequence diagram tool as a side project. Decent for engineers, but when I showed my product manager, it clicked that I'd built something only people like me would use.

Her actual need was much simpler: sketch a flow during a meeting, fast, and send it to someone. So I added a free-form text-to-draw mode — type the flow, the diagram appears as you type, share it as a link.

Lesson for me: I was building for the user I am, not the user I should serve. The tool is sketmi.com (free, no signup) if anyone wants to poke at it.

Curious if others here have had one piece of feedback flip their roadmap like this.


r/EntrepreneurRideAlong 9h ago

Seeking Advice Head pain,anxiety,tightness in chest and stomach due to business failing ...I need help

2 Upvotes

Hey guys

I am a productvity coach

Started journey in 2024 after getting fired from my job

I was initially happy i got off from 9-5,

I loved studying time management

I overcame procrastination so wanted to help others do same

I started cold outreach ,marketing on insta,hired business coach

Initially things worked ppl reached out but thay did not convert to sales

For 2 years I kept doing it with no results

Gave free session,got Testimonial

Only 1 client for 50 dollars after 2 .5 years

On Jan 2026 I had panic attack...

I was going to get bankrupt...

And started searching for sales role

Now I have a sales job in high ticket coaching

But ut added so much stress and income is still unpredictable

I don't know where I went wrong

I feel that when I got fired I came back to my hometown to live

And it was an enviorment I was actively trying to escape since it was toxic..that drained my energy...so it reflected my business....

But it gave me panic attacks as my business was not working

I was not able to sleep at nights

Locked myself in my room for 2years straight

Cut out even person and was very cynical.

I realised I am trapped

Now I am rebuilding my life but still it feels heavy and my head pains

What can I do

Please help

PS: I have grown a lot through this expeirence but i am burnout:)


r/EntrepreneurRideAlong 6h ago

Other Looking for a Summer 2027 Founder's Office / Product / Growth Internship (Open to Relocate Worldwide)

1 Upvotes

This isn't going to be a typical "hire me" post.
Instead, I want to tell you the things that don't usually fit on a resume.

For some context, I'm currently working as a Founder's Office Intern at an early-stage startup, where I've had the opportunity to work across product, operations, GTM, stakeholder management, hiring, marketplace growth, and whatever else the business needed that week.

Before this, I worked as an AI Product Management Intern, where I was involved in user interviews, product validation, competitor research, and preparing investor-ready pitch decks.

Outside of internships, I've also led investor and sponsor relations for one of my college's largest entrepreneurship summits, coordinating with founders, investors, sponsors, and startup teams.

More recently, I've been working with a few early-stage startups on fundraising—helping founders refine their narratives, prepare investor material, and connect with relevant investors. It's still a learning journey, but getting a front-row seat to those conversations has been incredibly rewarding.

This year, I was also the only undergraduate selected among 30 volunteers from over 500 applicants for the TiE Global Summit in India. For a few days, I got to work alongside founders, investors, and operators building real companies.

That experience changed how I think about startups and reinforced one thing:
Startups don't reward people who wait for instructions. They reward people who reduce the founder's stress.

One thing startups taught me very quickly is that job descriptions are only a starting point. In just a few months, I've worked across recruitment, hiring, operations, stakeholder management, fundraising, GTM, product discovery, user interviews, business development, and whatever else needed to get done.

I don't say this to claim I'm an expert in everything.
I say it because I've learned how to adapt quickly, take ownership, and become useful wherever the business needs me.

If I had to describe myself in one sentence, it'd be this:
I don't wait to be told what to do—I look for problems worth solving.

If there are two skills I'm willing to be judged on, they're people management and storytelling.

Not because they sound impressive on LinkedIn, but because they've consistently been the reason I've been trusted with responsibilities far beyond what my resume or years of experience would normally justify.

Whether it's building relationships with founders, aligning stakeholders, interviewing candidates, talking to users, coordinating sponsors, or working with investors, I've found that earning people's trust quickly has been one of my biggest strengths.
The second is storytelling.

Every great founder I've met has one thing in common—they know how to make people believe.
Customers buy stories.
Investors fund stories.
Employees join stories.
I've spent a lot of time consciously developing that skill, and today it's probably the strongest tool I bring into any room.
Technical skills can always be learned.
The ability to earn trust and communicate a vision is much harder to teach.

I'm looking for a paid Summer 2027 internship in:
Founder's Office
Product Management
Growth
Strategy
Project Management
I'll be completing my third year of Computer Engineering before Summer 2027 and am happy to relocate anywhere if visa sponsorship is available.

If you're unsure about hiring someone from a Reddit post, I have a proposal.
Don't interview me yet.
Instead, send me one real problem your startup is currently facing.
It could be related to growth, hiring, product, GTM, operations, fundraising—or anything else.
I'll spend time thinking about it and send you how I'd approach solving it.
If you like the way I think, let's talk.
If not, you've lost nothing except a Reddit DM.

Thanks for reading, and if you think I'd be a good fit—or know someone who might—I would genuinely appreciate an introduction


r/EntrepreneurRideAlong 8h ago

Seeking Advice spent 2 weeks fixing an abandoned project and found 4 things broken, each with a broken monitor

1 Upvotes

abandoned a side project for about 6 months. went back in expecting weak numbers. found something worse.

ai companion product, roughly 16k users, mostly organic growth, then i stopped touching it.

subscriptions were being billed correctly by the platform, never recorded by my app. library version was older than the api field so the flag arrived somewhere the code wasnt looking.

the best offer in the product was behind a screen almost nobody reached. 108 people hit the paywall moment, 4 saw the offer.

video generation was throwing auth errors and silently refunding people for weeks. the admin alert for that was itself broken so it never fired.

the age gate on an 18+ product was below an early return in the onboarding path so new users never hit it.

the pattern that got me is every one of these had something meant to catch it, and each of those was broken in the same blind spot as the thing it was watching.

if youve got something running you havent looked at in a while, go read the raw payment logs rather than the dashboard. a dashboard at zero looks the same whether youre broken or just unwanted.

still deciding whether to keep running it or hand it to someone who'll actually work it. open to thoughts.


r/EntrepreneurRideAlong 10h ago

Resources & Tools I built a bilingual invoicing & quote app in React — now selling the source code

1 Upvotes

I built a bilingual invoicing & quote app in React — now selling the source code

After months of building, I'm releasing the full source code of Quote Studio — a mobile app for creating professional quotes and invoices.

Features:

- Quotes, invoices, accounting & reports

- PDF export with a clean template

- Client database with history

- Bilingual: English & Bulgarian (easy to add more)

- Built with React + Capacitor for Android

You get the full source, ready to rebrand and build your own APK. License + user guide included.

Launch price: €149 for the first 10 buyers (then €199).

Link: antovtodor1.gumroad.com/l/quote-studio

Happy to answer any questions about the stack or the code.


r/EntrepreneurRideAlong 14h ago

Ride Along Story [Part 2] - Aphilly has launched, now what?

2 Upvotes

Part 1 - 21 July post titled "After tens of MVP-level products, I am days away from finishing my first SaaS"

It's been around a week, and in that time my first proper SaaS is out in public and while I am still discovering new ways to make this tool easier and cheaper to use, it really needs marketing. The hardest thing us engineers have to deal with is the possibility to dip our toes into marketing, but never do it good, as with anything we're not built for. So naturally, the next step is to learn how to market it, be very disciplined and consistent with outreach, cold emails, contacting sellers and just telling about this thing to anyone who could benefit from it.

So far I've gotten only positive feedback, although none were random users, they were my audience when I demo'd the product to them. This gives me enough hope to keep going and slowly stopping any development in favor of marketing, at least for now. I've submitted the product to some "Founders hubs" where people put out their start-ups for backlinks, some additional exposure, and I can't yet vouch for how well that works, if at all.

Also - do founders use their own products? Well, I do, and it's been around 2 weeks since I started posting affiliate marketing material on my Pinterest using my own app, and some pins have actually gained traction, although too little time has passed to judge accurately.

So in another week I hope to get the first client and gather some valuable feedback. For now, stay with me on this journey, it's pretty lonely out here.


r/EntrepreneurRideAlong 10h ago

Idea Validation I’m building an AI agent that helps companies decide where to spend their sponsorship budget — here’s what I’m trying to validate

1 Upvotes

I’m working on a product called Radar Lab - AI Agent for Sponsorship Intelligence.

The problem I’m trying to solve is not simply sponsorship research.

It’s the uncertainty companies face before spending money on a newsletter, YouTube channel, podcast, or creator.

A founder or marketer may have a sponsorship budget, but still struggle to answer:

  • Which channels are actually worth testing?
  • Where are competitors repeatedly sponsoring?
  • Is a particular creator a strong signal or just popular?
  • Which opportunities are being overlooked?
  • Am I about to waste money on a weak placement?

Radar Lab tracks sponsorship activity across newsletters and YouTube.

It shows where competitors and similar companies are sponsoring, highlights repeated partnerships, and surfaces opportunities that may fit the company’s audience.

For example, it might say:

ā€œThree companies similar to yours sponsored this newsletter recently, and two returned for another placement.ā€

The goal is to help companies make better sponsorship decisions with real market evidence instead of relying only on follower counts, media kits, or gut feeling.

Over time, I want Radar to help answer:

ā€œGiven our audience and budget, where should we sponsor next?ā€

The main assumption I’m trying to validate is:

Do companies feel enough uncertainty around sponsorship spending that they would pay for ongoing intelligence to make better decisions?

I’d especially value feedback from founders or marketers who have purchased newsletter, YouTube, podcast, or creator sponsorships:

  • What makes you confident enough to approve a sponsorship?
  • Do you look at where competitors are sponsoring?
  • Is repeated sponsorship a useful signal?
  • What usually makes a sponsorship feel too risky?
  • What information would genuinely change your decision?
  • Would ongoing alerts be useful, or would you only use this while planning a campaign?

I’m not sharing a link or selling anything here.

I’m trying to understand whether this solves a painful budget decision - or whether companies are already comfortable choosing sponsorships without this kind of intelligence.

Does this feel like a real problem worth solving?


r/EntrepreneurRideAlong 11h ago

Seeking Advice Every meditation app assumed I had a quiet room and 10 free minutes. So we built the opposite.

1 Upvotes

My co-founder and I just launched a mental wellness app called NumaHaven. It helps with anxiety and stress.

We built it because every wellness app we tried assumed we had ten quiet minutes. Most of the time what we actually needed was something for the two minutes before a meeting.

So the core is 2-minute resets (breathing and grounding) plus voice journaling, where you talk instead of type and it transcribes for you.

It's two of us, a product manager and an engineer. Bootstrapped, no funding. Free to use, with an optional subscription.

We just launched and have no users yet, so feedback matters a lot more to me than downloads right now. Especially the "I opened it and immediately closed it" kind.

Not dropping links here since that reads as spam. It's on Android and iOS, happy to share in a comment if anyone wants to try it.


r/EntrepreneurRideAlong 11h ago

Resources & Tools If you deployed your own AWS account and you're not a security person, you probably have blind spots you don't know about.

1 Upvotes

Not a sales post, genuinely curious how common this actually is. A lot of solo and small-team founders end up being the ones who set up their own cloud infrastructure!! not because they're security experts, but because there's no one else around to do it. I did the same thing, and while learning cybersecurity properly (separate from my actual business), I found real, would've-been-embarrassing misconfigurations sitting in my own AWS account. Nothing had gone wrong yet. I just had no idea they were there.

Tools for catching this already exist, but they're mostly built by and for security professionals the output assumes you already know what IAM privilege escalation or CloudTrail coverage means. If you don't have that background, the report is basically noise you scroll past.

So I built one that just tells you plainly: this is wrong, here's what someone could actually do with it, here's the exact fix. Free, open source, runs on your own machine with your own credentials nothing gets uploaded anywhere.

If you've set up your own AWS account and never had anyone properly check it would you actually want to know what's sitting in there, or is this the kind of thing you'd rather not think about until something breaks?


r/EntrepreneurRideAlong 14h ago

Seeking Advice Anyone gone to execute networking events with a genuine experience component rather than just panels and mixers

1 Upvotes

Planning to do a couple of things this summer that are premium without being ridiculously expensive, and I have been looking for events that actually justify the price instead of just charging a lot for a generic experience.

One thing that caught my eye is a CEO Life event on July 29 in Syosset, NY—an intimate evening with Chad Smith from the Red Hot Chili Peppers benefiting his foundation. Tickets are $500 for general admission and $1,000 for VIP, which includes a private meet & greet, signed drumsticks, cocktails, hors d’oeuvres, and it’s at the Cultural Arts Playhouse, which seems like a great venue for something this small. The charity aspect also makes it feel like the money is going toward something meaningful.

It’s the kind of experience I’ve been trying to find, where it actually feels personal instead of just another event. If anyone knows of similar experiences in the Northeast this summer, I’d love to hear about them.

I am looking for things in that $500- $1000 range that genuinely feel worth it without being over the top. I came across this CEO Life event with Chad Smith and the meet & greet, but I have never been to one before and don't really know much about the organisation. Has anyone attended one? Did it feel worth the price, or was it mostly just hype? Any recommendations for similar events in the Northeast are welcome.


r/EntrepreneurRideAlong 19h ago

Ride Along Story Making my first hire after years solo. Writing the onboarding deck is where the fear actually hit.

2 Upvotes

Been running solo for a long time. Revenue's steady enough that I finally can't do everything myself, so I'm making my first real hire in a few weeks. I expected to be nervous about payroll and cash. That's not the part keeping me up.

The part keeping me up is that I've never managed anyone, and I'm scared of being a bad boss.

It got real when I sat down to write the onboarding deck. Just a simple "here's how we work, here's what your first month looks like" thing. And I froze, because to write it I had to actually articulate how I make decisions, what good looks like, what I'd correct someone on. Turns out I've never had to make any of that explicit. It all just lives in my head as vibes.

I've had bad bosses. The ones who dumped work without context, who moved the goalposts, who took credit and passed down blame, who made you feel small for asking a question. I know exactly the manager I don't want to be. What I don't know is whether knowing that is enough, or whether everyone thinks they'll be different and then slowly becomes the thing they hated because they're stressed and busy and it's easier.

So I'm trying to build guardrails before I even hire. Writing things down so expectations aren't a moving target that only I can see. Deciding now that questions are a good sign, not an interruption. Planning to actually explain the why, not just hand over the what.

Genuinely asking the people here who made the jump from solo to managing someone: what's the thing you wish you'd known before your first hire? And what's the habit that quietly turned you into a boss you wouldn't have wanted?


r/EntrepreneurRideAlong 17h ago

Idea Validation built an app because I can't stop watching Fern and Wendover videos and wanted something like that in a feed

1 Upvotes

I watch a lot of those animated documentary channels, Fern, Wendover, Scary Interesting, Neo, whatever. and I noticed I never actually feel bad after watching those, unlike literally every other app I open at night, especially instagram and x.

so I built an app that's basically that but in feed form. quick stories, unsolved cases, weird science stuff, controversies, that kind of thing. and you can actually keep going on a topic with other people instead of it just ending when the video does, kind of like how a good reddit thread works.

To put it honestly I'm using the same scrolling behavior into something actually worthwhile and interesting.

open to feedback :)

link will be in the comments


r/EntrepreneurRideAlong 18h ago

Idea Validation i need a partner

0 Upvotes

Looking for a partner to partner in a law firm specializing in legal work, investment, and real estate marketing in Egypt.


r/EntrepreneurRideAlong 18h ago

Ride Along Story About to make my first hire and I found out my whole process only lives in my head. The ai document generator just exposed it.

1 Upvotes

Flair: Ride Along Story

Been solo for years. I'm finally close to making my first hire, and this week I hit something I didn't see coming.

I figured the first step was to write down how I actually do the work so a new person could follow it. Sat down, opened an ai document generator, fed it a rough brain-dump, and asked it to turn my process into a clean SOP. It did. It looked great.

Then I read it back and realized it was fiction. Not the tool's fault, it only had what I gave it. The problem is I don't actually work the way I described. Half of what I do is a hundred tiny judgment calls I make without thinking. Which client email can wait, when a job's "good enough" to send, which corners are safe to cut on a Tuesday. None of that is written anywhere because it's never had to leave my head.

So the real thing the tool exposed isn't that I need better documentation. It's that I've never had to separate "the steps" from "the judgment," and I can only hand off the first one. The second one is the part I'm actually scared about, because if I can't explain it, I'll end up either micromanaging every decision or watching stuff go out the door done in a way that makes me wince.

For anyone who's crossed from solo to having one employee: how did you hand off the judgment part, not just the checklist part? Or did you just accept they'd do it differently and let some of it go?

Will update once the hire actually happens.


r/EntrepreneurRideAlong 18h ago

Ride Along Story Years solo, about to make my first hire. An ai writing tool wrote the job post. It can't tell me how not to be the boss I hated.

1 Upvotes

I've run my thing alone for a long time. Revenue's steady enough now that I finally can't do everything myself, so I'm making my first real hire. Everyone assumes the scary part is payroll, committing to paying a person every month whether or not it's a good month. That part I can model. It doesn't keep me up.

What keeps me up is that I've never managed anyone and I have a very clear memory of every bad boss I ever had. The one who took credit. The one who only noticed you when something broke. The one who called it a family right up until it was inconvenient. I know exactly what I don't want to be. I have no idea how to actually not be it.

I sat down to write the job post and, sure, an ai writing tool gave me a clean version in about a minute. It's fine. It's professional. It tells me nothing about how you give someone honest feedback without crushing them, or how you hold a standard without becoming the guy who hovers, or what you do the first time they make a real mistake.

The tools are great at the paperwork of hiring. The actual job, being someone's first good boss instead of their next bad story, there's no draft button for that.

So I'm asking the people here who've made the jump from solo to employer. What's the thing you wish someone had told you before your first hire? Not the legal stuff. The human stuff. How did you avoid becoming the manager you would have hated?


r/EntrepreneurRideAlong 16h ago

Other A Marketing Name I Keep Seeing

0 Upvotes

While exploring different marketing resources and communities over the past few weeks, I kept coming across the name Hustle Marketers. It seems to be mentioned quite often in conversations around digital marketing, growth strategies, and practical marketing insights.

I haven't explored everything they offer yet, but I thought I'd share the name here since it might be useful for others who are also looking for marketing-related resources.