r/advancedentrepreneur

I thought opening a smoke shop would be pretty simple at first. find a decent spot, get the licenses, fill the store and start selling.

But the more I dig into it, the more questions keep coming up. Suppliers, payment processing, what products are actually worth carrying, hiring, keeping inventory under control, getting customers back, etc.

for anyone who's actually run a smoke shop, what part ended up being harder than you expected?

Was there anything you didn't think much about before opening that became a big issue later?

I'd rather hear about those things now than find out after putting money into a location.

I’m a 22yo guy living in South Korea I’ve been thinking about business ideas almost every night since I was young, and today is actually the first time I’ve decided to ask a question here

I’m curious to hear from people who have built marketplaces before

When u were just starting out, where did ur very first sellers actually come from?

I’m especially interested in the period before u had meaningful traffic or brand recognition

Did u:

* Reach out to potential sellers directly?

* Use Reddit, Facebook groups, or other communities?

* Offer incentives or reduced fees?

* Get ur first sellers through personal connections?

* Run paid ads?

* Or use another approach that worked surprisingly well?

I’d be particularly interested in hearing what actually worked in practice, rather than what u expected to work

If u built a marketplace from zero, how did u get ur first 10 to 100 sellers?

one more thing I’d like to mention is that I’m planning to target the US and European markets

There’s so much lead generation advice that gets repeated because it sounds right.

“Just personalize your cold emails.” “More outreach = more leads.” “Follow up 7–10 times.” “LinkedIn is the best channel.” “Run ads and let the algorithm find your buyers.”

What’s one lead gen tactic you’ve actually tried that didn’t live up to the hype?

And what worked better for you instead?

I’ve been building websites and trying to monetize them since 2007–2008.

I started making real money online around 2009–2010, and in 2011 I quit my job and became a full-time entrepreneur.

For the next 12 years, entrepreneurship was my life.

Most of my businesses were built around working alone. I learned SEO, paid advertising, affiliate marketing, lead generation, and online partnerships. I built some sites that did quite well, and overall, I’d say I was reasonably successful.

But there was a flaw in the way I was building everything: I was operating almost entirely in solitude.

In 2021, I decided to completely change direction. I wanted to rebuild my identity publicly, put myself out there, and pursue a different kind of entrepreneurial path.

Ironically, that brought a lot of positive attention. People praised what I was doing, and I started chasing the lifestyle that came with it.

Then came lifestyle creep.

Looking back, I invested way too much time, money, and energy in the wrong things. I lost focus on what had actually made me successful in the first place.

Eventually, reality caught up with me.

In 2024, I had to take a regular job again – doing essentially the same type of work I had previously done as an entrepreneur, but now as an employee.

That was difficult to process after spending 12 years building my own businesses.

But I still want to come back to entrepreneurship.

It’s in my blood. More importantly, I value freedom and independence too much to simply accept that this is where the story ends.

The difference now is that I’m trying to approach it with the lessons I’ve learned.

My energy isn’t what it was 10–15 years ago. I have more responsibilities, less time, and considerably less appetite for wasting years figuring things out the hard way.

I already have a routine. I’ve structured my schedule, written down my goals, and created an actual plan.
The problem is that progress feels incredibly slow.

I’m curious about people here who have gone through something similar.

If you’ve had a successful entrepreneurial period, lost your way, went back to employment, and then tried to rebuild your business again later in life:

What did you do differently the second time around?
How did you manage your energy and time?

How did you avoid getting distracted by lifestyle, ego, or things that look like progress but really aren’t?

And most importantly, what helped you actually regain momentum?

I’m not looking for a motivational speech. I’m interested in practical lessons from people who have actually been through it.

What would you tell your past self if you had to start again?

Let's say you're a DTC (Direct-to-Consumer) Brand for hobbyists and specialize in selling chess boards.

When you're DTC, the biggest roadblock you face is the absence of tangibility.

Your buyers are unable to visualize how the chess board will look on their table and what size the pieces are.

So obviously, just like most chess brands, you throw up the dimensions of the boards.

But do you think that's enough?

Why not give more?

Think of it.

When you provide the dimensions, you're assuming the buyer has a measuring tool on them or has the willingness to over exert their hippocampus (part of brain that stores spatial memory) just to buy your $30 chess board.

Why not also have a photo of the chess board in play, being used by people.

Because now the buyer doesn't just see how the board and pieces look on the table, they can gauge the actual scale through the people using it in the photo.

Give and give more. You will get and get more.

I launched a skill-based gaming platform about a week ago where players compete against each other for predetermined prizes based on their performance.
We had a strong first week, mainly from one customer who really liked the platform and generated a lot of activity quickly. Whop has now suspended us as an “unsupported business.”
My biggest concern is that there’s a significant balance locked in the account. A large portion is my own money that I put into the platform, plus revenue we’ve made, and I still have player payout obligations.
Has anyone dealt with this before?
What’s the best way to get the remaining balance released if Whop won’t reinstate us? And what payment processors actually support skill-based gaming/contest businesses?
I’m looking for a processor that will approve the business model upfront — not trying to hide what we do.

First of all, thanks to anyone who actually reads this whole thing. I know we’re all supposed to be running our businesses instead of reading strangers’ existential crises on Reddit, so I appreciate it 😂

I’m 18 (I’ve been deeply involved in the business for 2 good years now, please don’t laugh 😆) and I’m a partner in a construction and renovation business with my father. I have real responsibilities (estimates, clients, suppliers, projects, admin, etc.), so when I don’t perform, it actually affects the business and other people.
My problem is consistency.

I’ve had extended periods where I’ve been extremely productive. I can work hard, stay focused, take responsibility, get shit done, and genuinely enjoy doing it. I’m ambitious as hell and I love business.

So I know I can work. That’s what makes this so frustrating.

I seem to go through cycles where I’ll be doing great for months, then gradually start procrastinating more and more until I can literally sit in front of my computer with important work waiting and somehow waste hours doomscrolling, watching shows, browsing random shit, etc.

And the funniest part is that I don’t even enjoy procrastinating.

When I’m relaxing, I’m thinking about how I should be working. I tell myself that as soon as I get back to the office I’m going to work my ass off.
Then I sit down at the computer and my brain suddenly wants to do literally anything except work.
So I end up neither working properly nor relaxing properly. Fantastic system. 10/10.

I’ve also realized that I live in the future way too much. I think constantly about what we could build with the company, where I could be in a few years, financial goals, the life I want, etc.

It motivates me, but sometimes I think I’m basically getting high on my own future instead of doing the boring work required to actually get there.
Eventually reality hits, I get pissed off with myself, have a massive burst of motivation, become disciplined again… and sooner or later the cycle repeats.

And this isn’t really a knowledge problem.
I know about time blocking, website blockers, putting the phone away, exercise, routines, planning the night before, breaking tasks down, etc. I’ve tried systems and they work, until I stop following the fucking system.
That’s what I actually want to solve.

I don’t want to need motivation, guilt or panic to function. I want to become boringly consistent. I want to work hard when it’s time to work, be someone people can rely on, and then actually enjoy my free time without feeling guilty.

So I’m mainly asking people here who genuinely recognize this pattern:

If you used to be like this and eventually became consistently reliable, what actually changed?

Environment? Accountability? Removing easy stimulation? ADHD treatment? Learning to tolerate boredom? Better separation between work and free time? Simply growing up and developing discipline? Something else?

Most importantly, what made it stick after the initial motivation disappeared?

I’m already going to find a therapist and get properly evaluated, including for possible attention/executive function issues, so respectfully, I don’t need 50 people telling me “go to therapy” or diagnosing me from a Reddit post. I’m handling that separately.

I’m looking for lived experience from people who can genuinely say:

“Yeah, I used to operate like this. Here’s what I learned.”

Thanks in advance for any input, especially from people who’ve actually been through it.

whats your first message to your potential clients, when u just want to get their feedback without annoying them?

especially if these people are not your friends, so theres no warm intro, no shared context, nothing. just me reaching out cold and asking for their time.

im trying to figure out how much to put in that first message,

- do u say straight away that u re building something and want feedback?
- or do u start with a question about their work and get to the point later?
- how long should it be? 2 lines? a short paragraph?
- do u ask for a call or just keep it in text so its easier for them to reply?

if u have a message that actually worked for u, id love to see the actual wording,

thanks!!

Hi everyone,

I’m from India and I’m planning to start a small business from home with a budget of around ₹50,000 (approximately $600).

I want to start solo, without renting a shop or hiring employees initially.

My situation:

Budget: ₹50,000 maximum

Location: India

Work setup: From home

Team: Just me initially

Available time: Around 4–8 hours/day

Goal: Build a real, sustainable business rather than a quick-money scheme

I’m open to both online and offline businesses.

I’m also willing to learn a new skill if the opportunity is good.

I already have some experience with HTML, CSS, JavaScript, basic Python and website development, but I don't want to limit myself to technology. I’m open to completely different business ideas as well.

I’m especially interested in businesses that can start small and gradually grow.

What would you do if you were in my position?

I would really appreciate advice from people who have actually started a business, especially solo founders and small-business owners.

If possible, please tell me:

What business would you start with this budget?

How much would you initially invest?

How would you get your first 10 customers?

What would the expected monthly expenses be?

What kind of profit margin is realistic?

What was the biggest mistake or challenge you faced?

Can the business eventually scale beyond a one-person operation?

I’m open to ideas from India or other countries, as long as the model can potentially be adapted to the Indian market.

I’m not looking for get-rich-quick schemes. I want practical advice based on real experience.

Thanks in advance to everyone who shares their experience. 🙏

We got our first few B2B customers with me doing basically everything myself finding companies, sending emails, following up keeping notes wherever I remembered to put them. It was fine with maybe 10 conversations going but once that became 40 or 50 I started forgetting stupid stuff follow ups sitting for 4 days accounts I researched twice because I forgot I already did it so that kind of thing.

I spent a weekend cleaning the whole process up and realized I was doing way more sales admin than sales. Started moving the repetitive parts into one flow and keeping my time for picking accounts and talking to people it's running better now but kind of weird how quickly founder led sales turns into managing a little sales operation without you noticing

Throwaway-adjacent framing, but the situation is real and I want honest reads from people who've actually sat on a cap table, not theory.

Three of us starting a company. Two of us handle the build side, the third runs sales and commercial. From the beginning we agreed on roughly equal thirds. Now, before anything is signed, the commercial co-founder is saying he needs a clear majority for himself, with the two of us splitting the rest, and his stated reason is that "investors won't fund a startup that doesn't have a majority shareholder."

I've been around long enough to be suspicious of a reason that happens to benefit the person giving it, but I also don't want to torch a good partnership over paranoia if this is a genuine market norm I've just never run into.

What I've considered so far:

One, I've never actually seen an investor require a single founder to hold over 50%. If anything I've heard the opposite, that heavily lopsided founder equity this early is a yellow flag for later rounds because it leaves the operators with too little to stay motivated through dilution. But my sample size isn't huge and I could be wrong.

Two, I keep thinking the real issue he's pointing at is control, not ownership, and those are separable. You can give someone decision-making authority through board structure, a casting vote, or defined decision rights without handing them the economics of a majority stake. If control is the actual need, there are cleaner instruments for it.

Three, the part that bothers me most is timing. We have no term sheet, no investor in the room, no raise underway. Solving a hypothetical future investor's hypothetical preference by permanently reshaping equity today feels backwards. If it ever becomes a real requirement from a real check-writer, we can revisit it then, with leverage and specifics.

So my questions for people who've been through a raise or a co-founder split:

Have you ever actually had an investor demand a majority shareholder as a funding condition, or is this folklore?

And if the underlying need really is control rather than ownership, how did you structure decision rights without lopsiding the cap table? I'd rather solve the real problem than trade equity to settle an argument.

When coming up with startup ideas, what do you guys do when an idea you have has already been built by someone else. It's almost impossible to think of a completely new idea so with this competition, how do you know if you should pursue it further or if the competition is more likely to just beat you?

For example, I was thinking about creating a dev tool which is largely an LLM that understands your screen and recent tasks already, so that you don't have to provide the context to your agent every time. Instead they already know what's happening and what you're working on. Upon doing more research, i found a company called "littlebird" which has ~40 employees, passed an initial seed round, and is already a pretty established app which does something similar.

For cases like this, how do you know if you should just move on, or find a wedge within the competition?

So there’s an interesting stage of growth where the business is clearly past the point of “the founders can just figure it out.” Where you basically start running into problems that really need someone who has fixed it before better operational systems, proper financial planning, a real marketing strategy, stronger technical decision-making, etc. But at the same time, hiring a senior person full-time feels premature.

The workload might not justify a 40-hour-a-week executive, and the fixed cost is difficult to justify when you’re still trying to keep the business lean. This turns out to be a surprisingly awkward stage.

You don't necessarily need another employee. You need senior judgment someone who can come in, make the right decisions, put the right systems in place, and potentially help the existing team execute them.

I'd like to know how other founders handled this stage when they reached it.

I'd be more interested in hearing about what you actually did and how it played out than generic advice.

Hey guys, happy Sunday ! Just curious, what distribution platforms do you all use for your products ? 🤔 Trying to expand to get my first client in

I'm debating whether entrepreneurs should invest time in creating videos, sharing their expertise, and discussing trends in their industry.

Does being visible as the founder actually help generate trust and business? Or is it more effective to keep the focus entirely on the company and its products or services?

I'd love to hear from founders who've tried both approaches. What worked better for you, and why?

I've been burned before by projections that looked solid on paper but fell apart once a client paid late or an unexpected expense hit, so I'm skeptical going in. How accurate is cash flow forecasting software really, especially for a business like mine with irregular income and seasonal swings? I want to know if the accuracy holds up in practice or if it's just a polished guess dressed up as a forecast.

when my last company got acquired, i was forced to give up equity i'd negotiated for in the apa, because of bureacratic laws of my home country which make it hard for me to own equity in a foreign llc.

in retrospect, i probably could have gotten better lawyers and ironed it out but in the moment, after a gruelling acquisition proccess and facing health issues - i was tired and just wanted to let go, so i relinqueshed my equity. this came to bite me severely later on as the company grew much larger, was acquired by a public company in cash and my equity would have been worth much more than the cash i got for the initial acquisition

this has left me quite paranoid and i have been researching ways founders/co-founders are forced to let go of their equity - to avoid chances of this happening again

if you/someone you know has been through something similar, can you please share the story of how it happened, what could have been done differently and if there was any resolution?

Hey {{firstName}},

Saw {{companyName}} is scaling paid ads.

I took a look at your site and found 5 things that could be costing you conversions from traffic you’re already paying for and put them in a short checklist.

I do CRO for DTC brands and recently helped {{cantmentionnameonreddit}} generate an additional $111,000/year in revenue from a 3-week test.

Let me know and I'll shoot the checklist over to you?

Best,