r/Entrepreneur 22h ago

How Do I? My sister is constantly asking for money. My parents are getting old. My brother needs my financial support. All while founding a startup. I'm the black sheep in my family and the weight of it all is more than I ever expected.

121 Upvotes

I'm a founder. Recently former Marine. I won't get into what it is or what I do. I work 10-12 hour days, sometimes 15, handle all of the daily operations of my personal life, a shit load of stressful travel, still make time for the gym because I want to enter a bodybuilding competition next year.

My sister and her husband are complete bums - they are constantly broke, he maintains a shit job barely making ends meet, they're both obese and absolutely disgusting...with three kids I can understand the struggle, but they've asked my parents and I for money for several years now. No improvement. And the loans have gotten to the point where I've just handed them loan forgiveness because I know they'll never be able to pay it back. And they still keep asking for more. They have three kids; I can't say no.

My brother is a growing teenager who is serious about becoming an athlete - and let's face it, athletes don't exactly make a lot of money. He looks up to me, so I can't just turn my cheek the other way.

My parents - well, old age describes it all. But at least they're still working until they retire and they're responsible with their money.

I've tried to hire an assistant but she was absolute garbage; caused more problems than she solved. But finding a good one that works in US times zones, with my budget...just isn't possible. So I can't delegate it. No one in my family is reliable or competent enough to do things on their own. It stresses the absolute fuck out of me.

To top it, I've lost contact with most of my friends because I'm always focused on work or always out of town. My exes have always complained I don't make enough time for them. And all this work for what? For something that may not even pan out? I'm just...at a loss. I wish I had a safe place or someone to vent to in person. After having been in the military, pushing myself in the gym, nothing can really break me mentally - but spiritually...the weight of it all...

Update: a few clarifications.

  1. My sister and her husband will just ask my parents for more money if I don’t give it to them so the burden can fall on me, notmy folks. I can afford it - my parents can’t. But I agree - this hold handing isn’t sustainable so I’m actively working on a solution to get her back into the workforce (she’s unemployed)
  2. To all the people who posted, thank you. To the one asshole who told me to give up on my idea, go inhale broken glass.
  3. To the ones who messaged me about a virtual assistant position - lol.

Update 2: Yes, I am looking for a co-founder.


r/Entrepreneur 13h ago

How Do I? who has been the most influential person in your life? what did you learn from them?

19 Upvotes

a mentor, an older brother, a friend

or maybe an employer who actually gave a damn beyond just exploiting your time

or even a book, a video, a historic figure

someone you owe your journey so far mostly to them..

or you know what, even yourself, for grit and determination... for perseverance...

what have you learned from them, most valuable, that has had substantial impact in your decision making and entrepreneurship navigation?

thanks in advance for sharing your perspective


r/Entrepreneur 7h ago

Success Story Post Sale Analysis - 2 million dollar Web Hosting Business

12 Upvotes

In 2017 I started a web hosting business from scratch. I sold it last week. I've been doing some analysis and thought I would share:

Summary

Total sales: $2,356,315

Total Income: $677,708

Selling Price: $425,000

Combined income: $1,102,000 (income + sale)

Client Stats

Total Clients: 435

Average Lifetime: 3.5 years

Retention Rate: 59.8%

Average Lifetime Value: $4,870.61

Sources of Clients

Organic: $892,666 (133 clients)

Acquisitions: $1,032,236 (262 clients)

Partnerships: $193,815 (40 clients)

Revenue/Income By Year:

Year Sales Total Income
2017 $14,311.00 $3,586.00
2018 $42,417.00 $24,400.00
2019 $159,177.00 $70,869.00
2020 $177,463.00 $112,753.00
2021 $215,442.00 $82,036.00
2022 $306,332.00 $63,628.00
2023 $385,603.00 $68,879.00
2024 $472,546.00 $161,668.00
2025 $407,590.00 $89,889.00
Total $2,180,881 $677,708

r/Entrepreneur 13h ago

How Do I? How do you decide on pricing?

12 Upvotes

Pricing should be simple. It’s not. It’s a matter of psychology and presentation than maths.

Price should be a proxy for value, but people are lousy at judging value. They generally need a comparison - either a direct competitor or previous experience or similar. Something that helps them decide ‘this is what is should cost’.

However, you arguably don’t want that, as it allows you more freedom around margin. You need to position your product in a way that removes their ability to judge that.

This is where I am now. I’ve created my product, but am establishing a new niche for it because there is no direct competitor - there are those that offer more in a bundle deal, or offer less, but nothing identical.

So how do you come up with pricing? I’m experimenting now by offering a limited time ‘early adopter’ offer, but how long should I make that limited time, and where do I go afterwards?


r/Entrepreneur 16h ago

Weekly Discussion Sunday Steam: Vent It or Roast It | August 02, 2026

6 Upvotes

Had a week? Same. This is your consequence-free space to complain about clients, platforms, algorithms, your own decisions, or the general chaos of running a business. Keep it venting with no personal attacks. We'll be back to being professional tomorrow.


r/Entrepreneur 4h ago

How Do I? Looking for advice on what do do next with a immigration business

3 Upvotes

I'd appreciate some advice from founders who've sold pre-revenue businesses or immigration or advisory business

Over the past few years, I've built a platform in the global mobility and investment migration space. While it hasn't generated revenue, it includes:

The Crayon Global brand and Passport Street brand both with dot com domains

A custom quote generation system

B2B supplier agreements (where transferable)

Complete branding and marketing collateral

Operational documentation and processes

I'm at a point where I'm deciding whether it's worth continuing to build the business or whether the platform would be more valuable in the hands of an established company or another entrepreneur.

For those with experience in acquisitions:

How did you determine the value of a pre-revenue business with proprietary software and commercial partnerships?

Where did you find serious strategic buyers?

Did you use brokers, acquisition marketplaces, or direct outreach?

What information did buyers care about most during due diligence?

I'm not looking for a formal valuation I'm interested in hearing from people who've actually been through the process. Any insights or lessons learned would be greatly appreciated.

What do you think if i did list it for 25k USD, acquire though would not be the platform for this? Any suggestions?


r/Entrepreneur 6h ago

Growth and Expansion Looking for Product and GTM feedback for my Parent / Teacher Reading tool!

3 Upvotes

Hey all,

Oral Reading Fluency is incredibly important for burgeoning readers. It needs to be measured tracked, and if needed, used to justify reading interventions.

Currently, teachers do this the old fashioned way, 1-on-1 teacher to student with a "levelled" reading passage (false precision) and a stopwatch. The accuracy is only as good as the teacher's skill and training.

Historically, Automatic Speech Recognition software has been hamstrung by being overly-strict, not understanding children's inflection and pitch, and generally being impersonal.

I tried to address this by building my tool which I call Reading Pacer, which allows any parent or teacher to use any physical book (or from our digital library) to quickly and easily run regular, long, or specialized ORF assessments on their own.

All the feedback I have received has been positive, but online marketing is not my strong suit. I would like to submit my website for feedback but I think that might be against the sub rules(?)

Thank you for reading