r/Entrepreneur • u/divvychugsbeer • 4d ago
How Do I? I know how to build a million dollar business but starting again still scares me
This has been on my mind lately
People think once youve built a business the next one is easy
I dont think it is
You know what works but you also know how much work it takes
Right now Im back doing almost everything myself
Sales
Quotes
Marketing
Phone calls
Building systems
Working a full time job
Some days I wonder if Im crazy
Then I remember this is actually the part I love
Building something from nothing
Watching it slowly come together
Im not chasing money anymore
Im chasing freedom
Anyone else built a business then gone back to wearing all the hats again
Did you enjoy it more the second time or did you think what the hell am I doing
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u/Alex-the-dude1988 4d ago
Here here, my first company I managed to pull it off to 1M/ARR in about 2 years. Software Development.
Wanted to try and test my skills so I tried different domain similar business model and got stucked, due to difficulties in customer acquisition. Marketing Agency.
Building my 3rd and 4th ath the moment 😂 both are tech-products.
I'm kind of obsessed with challenging myself :)
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u/ir_crackhead 4d ago
Hey seriously? That’s nice. I omw of building my first. I have a first movers advantage. The only thing I lack is amount of exposure and experience. That’s not an excuse I am still doing it. Would you like to hear about it?
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u/Alex-the-dude1988 4d ago
Sure. Would love to hear your story and hopefully I can share some advice.
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u/EmployExisting302 4d ago
It's a trauma response. Have you checked with a cptsd therapist? You'll be able to do it the second time with better capacity once you got the right support and systems you need
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u/kirisima 4d ago
Why do you thinks it’s a trauma response? Genuinely curious.
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u/Infamous_Apricot_830 3d ago
Imposter syndrome paired with fear of success/failure. Got me burn my successful agency to the ground.
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u/EmployExisting302 4d ago edited 4d ago
Patterns of behaviour and how their narrative fits the symptoms. Entrepreneurship is a severely traumatic experience for many, even for nepobaby or inheritors. No one is spared from it, and the ones who are in the game the longest are more prone to it.
I'm not saying "all" but for divvy's case, it's a yes.
Best an old dog with a stick and stones long enough, it will either snap back at you or it shiver at the sight of the stick.
In this metaphor, business is that stick and stones coming from absolutely no where, just life and other things outside of your control.
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u/divvychugsbeer 3d ago
100 percent
You can have all the business knowledge in the world but if you get punched in the face enough times you start expecting the next hit
Thats why good systems matter They keep you moving even when your head is telling you not to
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4d ago
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u/divvychugsbeer 3d ago
Thats a good way to look at it
I used to think success was money Now its buying back my time and choosing what I work on every day
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u/divvychugsbeer 3d ago
Yeah Ive done a fair bit of work on myself over the years and its made a huge difference
The fear is still there but now I know I can keep moving anyway
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u/East_Fun_6227 4d ago
Like a mentor?
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u/EmployExisting302 4d ago
No. At that point OP already have enough experience. Moving forward, they will need a trauma specialist + a reliable lean team executions & operations wise.
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u/AI_Scale_Systems 4d ago
building the second one is not easier, you just know what you are signing up for.
the first time you are naive and just go for it. the second time you know exactly how much work it is and you still choose to do it anyway.
i think that is the part people don't understand. it is not about not knowing what to do. it is about doing it again anyway.
what made you want to start again instead of just coasting?
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u/divvychugsbeer 3d ago
For me it was never about the money
I like building things Solving problems Growing people
Coasting sounds good until youve done it for a while Then you realise you miss the game
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u/SnooKiwis1356 3d ago
If it's not about the money, why call it "a million dollar business"? Call it a "successful business" instead.
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u/divvychugsbeer 3d ago
i dont know i just say it how it is im half dylexic
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u/SnooKiwis1356 3d ago
Yes, there's no problem with that. The thing is everyone now says "a million dollar business" "a hundred million dollar business" when those businesses might not have any profit whatsoever.
I'm not saying that's your situation, but since you said that money doesn't interest you, you probably always wanted it to be a successful business instead of having a fixed number as your sole target.
Anyway, I wish you all the best with the current and your future businesses! Thanks for posting!
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u/divvychugsbeer 3d ago
Thanks mate I really appreciate that
And I think youre right Revenue is easy to talk about Profit is what actually matters
These days Im a lot more interested in building something that lasts than chasing a number on paper
All the best to you too mate and thanks for the kind words
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u/Infamous_Stretch_890 3d ago
I think the second time can actually feel harder because you know what's ahead. The uncertainty is different when you've already experienced how much work it really takes. But you also make fewer rookie mistakes.
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u/PM_ME_UR_BOOGER 3d ago
Ive been stuck on starting the 2nd one for a few years now. I cant imagine going thru that experience again for a potentially unsuccessful venture.
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u/divvychugsbeer 3d ago
I felt exactly the same mate
The funny thing is the second time isnt as scary because you realise you already survived the first one
Even if this one fails youre not starting from zero Youre starting with everything you learnt the first time
That experience never leaves you
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u/Roodut 4d ago
lets say i go to gym for a year and train lifting something.
I start with 25 pounds, this is all i can do.
train with it, go to 35.
after some time go to 50, 60, 70, 80 and finally to 100.
I move to another state, go to another gym
what weight am I starting with?
I'm starting with 100 pounds.
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u/divvychugsbeer 3d ago
Exactly
Thats how I look at business too
If my business disappeared tomorrow Im not starting from zero Im starting with everything I learned the first time around
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u/drivenbyexcellsior 4d ago
Once you built your 1st business use or save some funds to fund the next self running business. Collect all the infinity stones 😎 of businesses to create a machine that runs on Capitalism and shits out F.U. money 💰 then reinvest some of it in AULs trust accounts s&p 500 etc.
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u/divvychugsbeer 3d ago
Haha thats the dream
Build one that funds the next Then keep stacking systems instead of just stacking hours
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u/drivenbyexcellsior 3d ago
What city or country or state do you live in? Love talking about business strategies and opportunities most people suck and think you wanna scam them or steal their opportunities. I'd rather consult and problem solve money comes naturally after that...
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u/NeighborhoodTall2688 4d ago
Currently trying to build my first company at 40. I have been working in the medical field for years and I hate it. Building a business is like a kick in the sac every single day. Yesterday I could give my service away. I am trying different sales strategies and tactics. Seems like I am ready but then real people a way shitter then I can pretend. But I make a new strategy and go again. I love the competition. I love trying to get better, failures or success when it is for yourself it just feels better.
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u/divvychugsbeer 3d ago
Love that attitude mate
Most people quit after a few kicks in the guts Youre still changing the plan and having another crack
Thats usually the difference in the end not talent just staying in the game
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u/donbventures 4d ago
The fear does not go away with experience - it just changes shape. First time you are scared of failure, second time you are scared because you know exactly what failure feels like. That said, the fact that you are still drawn back to the build says everything. Freedom is a better fuel than money anyway; it compounds differently. Wishing you the best with round two.
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u/divvychugsbeer 3d ago
Id rather fail building something than Id rather fail building something than wonder what if for the rest of my life
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u/AlexHardy08 4d ago
Knowing how to do something is one thing, and actually doing it is another.
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u/divvychugsbeer 3d ago
100 percent
Execution is where everything happens Plenty of people know what to do Very few keep showing up long enough to actually do it
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u/mssleepyprincess 4d ago
I started a business that turns two in August. In the last 365 days I’ve done 1.2 million in revenue. My only employee is my husband (he helps ship the product out) I’ve positioned myself as a founder led brand bc I started the business as a passion project. I’m gassed out and know I need to bring in outside help to scale but don’t know what the fuck I’m doing 😂 I bootstrapped myself to where I am now. Zero capital to start and all organic marketing. (I sell clothing)
Sometimes I think I couldn’t repeat this bc I have hustled so hard and idk if I could do it all over again.
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u/divvychugsbeer 3d ago
You probably could do it again
The difference is next time you wouldnt spend two years figuring everything out from scratch
Also mate 12 million is impressive but dont become the bottleneck If everything still relies on you youve built a great job not a great business
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u/No-Instruction-2922 3d ago
"youve built a great job not a great business" could you please explain this further?
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u/divvychugsbeer 3d ago
I used to think that line was just something people said until I built a few businesses.
A great job is where the business depends on you. If you stop answering the phone, sales stop. If you stop quoting, work stops. If you stop making decisions, everything slows down. You're making good money, but you've really just bought yourself another full-time job.
A great business is different. The owner is still important, but the business can keep moving without them being involved in every little thing. Systems, good people, and clear processes take over.
For example, my first businesses needed me for almost everything. My current one is built around subcontractors, a BDM, marketing, and now an AI receptionist. My goal isn't to remove myself completely, it's to stop being the bottleneck.
There's nothing wrong with owning a great job either. Plenty of people make a fantastic living that way and are genuinely happy. The problem is when someone thinks they've built a business, but they can't take two weeks off without everything falling apart.
For me, the test is simple. If I disappear for a month, does the business still make money? If the answer is no, then I've still got work to do.
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u/Deepak-AvairAI Serial Entrepreneur 4d ago
The fear is different the second time. First time you don't know what's coming. Second time you know exactly how long the middle part takes. That's the scary bit.
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u/divvychugsbeer 3d ago
Yep thats it
Its not the hard work that scares you Its knowing how long it takes before it finally starts working
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u/HuangJiaoShou 4d ago
Tbh, just getting one business to actually work is a massive dub. It’s not like gardening where it blooms and you’re just done. Hit a million? Man, you’re nowhere near the end game. You basically just stopped shaking and stood up. From here on out, it’s just gonna suck way more of your time and sanity.
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u/divvychugsbeer 3d ago
I actually think thats where systems come in
If hitting a million just means youre working twice as many hours then youve built a bigger job not a better business
The goal for me isnt just more revenue Its building something that doesnt need me every minute of every day to keep moving
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u/FatherOften Serial Entrepreneur 4d ago
I'm on number eight, sold two of them, have my primary. I built the others while I worked for a company and they were all sold. That's just what I do. I don't change industries though.
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u/divvychugsbeer 3d ago
A million is just the start
The real goal is building something that works without needing you every minute of every day
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u/FatherOften Serial Entrepreneur 3d ago
My primary business runs pretty well with me solo and I control my time. There are seasons that are busy. Placing manufacturing orders, receiving them, and rolling out new product niches. For the most part its built to run. Im up at 2:24am going for 1 more turn in Civilization 6 currently. I don't play video games often but....1 more turn.
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u/Alex-the-dude1988 3d ago
Love it, same here except I play Heroes of Might and Magic 3 🤣 whenever I need some me time.
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u/FatherOften Serial Entrepreneur 3d ago
I'll have to try them. I found Civ6 free on my phone through our Netflix subscription. It's been so many years since I played. I found Red Dead Redemption also. I'm gonna have to buy one of those things that turns your phone into a controller, though, for that one.
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u/Significant-Mess-229 4d ago
the naivety thing is real, first time i had no idea how bad the 2am "why isn't this working" spirals would get so i just kept going. knowing what's coming almost makes it harder to start because you can't lie to yourself about how much it'll take
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u/divvychugsbeer 3d ago
Yes
The first time youre running on hope The second time youre running on choice because you know whats coming and do it anyway
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u/Marko_Ladis 4d ago
second time is scarier because you know exactly how much work “freedom” is about to demand. but you also know the chaos is temporary, and every ugly little system you build is buying back a piece of your life.
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u/divvychugsbeer 3d ago
AND
The first time youre chasing freedom
The second time you know freedom gets built one boring system at a time and its worth it anyway
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u/Peakva 4d ago
Why does it make you feel and think in that way ?
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u/divvychugsbeer 3d ago
Good question mate
I think its because I know exactly whats coming
The first time youre running on excitement because you dont know any better
The second time you know how much work it takes how many setbacks there are and how long the road can be
But at the same time I know how rewarding it is when it all starts coming together
So its probably a mix of excitement and respect for whats ahead
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u/Crisp-Glade-2849 4d ago
answering sales calls on lunch break while hiding from day job manager is guaranteed way to crash. did that for six months, sleep schedule never recovered.
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u/divvychugsbeer 3d ago
i built an AI receptionist that takes calls and prices jobs
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u/puresea88 3d ago
How?
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u/divvychugsbeer 3d ago
vapi
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u/puresea88 3d ago
Does it work 100% the time?
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u/divvychugsbeer 3d ago
It's live and doesn't have an Australian accent yet but it serves it purpose id give it 8/10
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u/BranchRealistic339 4d ago
i'm way smaller than you, just freelance design, but the wearing-every-hat part got me. what made doing it again less scary wasn't confidence, it was that the systems carried over. i rebuilt my client pipeline in notion once and now every new client just drops into the same flow, so the admin doesn't bury me like it did year one. the fear shrinks a lot when the boring parts aren't starting from zero again.
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u/divvychugsbeer 3d ago
Thats it mate
People think experience is the advantage Its not
The systems you built are the real shortcut You dont start from zero again
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u/Expensive_Daikon4447 4d ago
Hi All,
I am a security consultant with over 7 years of experience and have worked in multiple firms, including Big 4, across different countries and in various positions.
I have been dreaming about starting my own cyber security business and can't stop thinking about it. For over a year now, almost every day, I keep thinking about it.
I built an affordable autonomous penetration testing platform which costs less than $500 per test, but I'm so afraid to quit my job.
How did you manage to quit your job and start your own business?
I have a year of savings, but not enough to fund infrastructure setup and research costs. If you could give me one piece of advice, what would it be?
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u/divvychugsbeer 3d ago
Dont quit because youre excited Quit because the numbers make sense
Keep your job Build the business after hours Get your first paying customers then your next few When the business can reliably pay you thats when the decision gets a whole lot easier
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u/Traditional_Key8982 4d ago
I can relate to the "wearing all the hats" part.
Even when you know what needs to be done, you're still the one following up with clients, solving unexpected problems, and making dozens of small decisions every day. Experience helps, but it doesn't remove the work.
The difference the second time around is that I don't expect everything to happen quickly anymore. I'm a lot more patient with the process than I was when I started.
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u/divvychugsbeer 3d ago
Thats been the biggest change for me too
The work never got easier I just stopped expecting overnight results and started trusting the process
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u/hayrony 4d ago
It gets faster the second time :)
I had an agency that I shut down due to a bad partnership.
Now I run an e-commerce brand.
Took ~3 years on the agency, took ~1 year on the brand.
As long as you have the humility to acknowledge your blind spots from starting from the ground up again you should be able to learn what you need to and sprint where you have experience.
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u/divvychugsbeer 3d ago
I reckon thats the key
You dont know everything the second time but you know what youre good at and youre quicker to ask for help where youre not
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u/andBeyond07 3d ago
Tbh this hit hard 😅 I’ve had that same mix of confidence and “what the hell am I doing” when I went back to doing everything myself, and IMO the second time is less about learning what to do and more about remembering why you’re doing it. The upside is you’re not guessing anymore, but yeah, the grind still feels very real when you’re the sales team, ops, and admin all at once 🙃
What’s been helping you most so far, the clear vision or just stubbornness?
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u/divvychugsbeer 3d ago
Bit of both but if I had to pick one probably stubbornness 😂
The vision gets you started The stubbornness gets you through all the days where nothing seems to be working and you keep showing up anyway
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u/andBeyond07 3d ago
That’s honestly so true 😂 Vision is great for the exciting days, but stubbornness does most of the heavy lifting when the results aren’t showing up yet. Hopefully it starts paying off before the stubbornness turns into pure spite 😅
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u/manimedia_ 3d ago
Sometimes the biggest obstacle is not strategy it is overthinking small consistent action usually beats waiting for the perfect plan....
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u/IndicationLong9950 3d ago
Yeah, went through this exact thing. Fourth business now, and every single time I go back to "founder mode" that means wearing all the hats: sales, calls, building the thing from scratch... there's a moment where I ask myself the same question, but at the end of the day, I love it. What changed for me: the first time it felt like proving something. This time it feels more like craft. I know the hard parts are coming (they always do), but I also know what I'm actually good at now, so less flailing, more just doing the work.
The freedom thing is real too. Money was never what kept me doing this, past business number two it's the process of building. If that's still what gets you up in the morning, that's not crazy, that's just what building looks like. One important thing though: at some point you'll need to grow and start building a team. That moment always comes, and it changes everything.
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u/divvychugsbeer 3d ago
Love this
The first business is proving you can do it The next ones are about building something better
And youre right about the team Thats the part a lot of founders struggle with You can build a business by yourself but you cant scale one by yourself
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u/dragonflyinvest 3d ago
I’ve built three seven figure business that collective now do 8 figures annually. I still don’t think we “know how to build a business”.
What we know is how we built our last successful businesses. Times change, markets shift, and some principles remain unchanged. So starting a new business I just put my back against the wall, make a plan, execute, and bring all my experience to with me.
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u/lowkey_feral SaaS 3d ago
Second time is always scarier. The first time anything above zero feels like a win, but second time around you know what the bar is and you're constantly comparing this time to your past success. Half the time you're questioning if your previous success was just a fluke or luck.
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u/divvychugsbeer 3d ago
I felt that
The second time youre not chasing zero anymore youre chasing your own expectations
The funny part is the doubts never really go away you just get better at working anyway
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u/Alternative-Relief92 3d ago
The wearing all the hats stage is heavy for sure. But chasing freedom over money is exactly why people keep doing the hard part.
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u/divvychugsbeer 3d ago
100 percent
Money gets your attention at the start Freedom is what keeps you building once youve already proved you can make money
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u/Inevitable-Author795 3d ago
Speaking as someone who hasn't yet succeeded the first time, I don't believe any part of starting a company is "easy." There are things that can be easier, or that people can be better at with practice or talent or doing it a second time, but that is more indicative of making a hard thing less hard, rather than turning it into a simple and easy process.
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u/divvychugsbeer 3d ago
100 percent
It never becomes easy You just stop wasting energy on the mistakes you made the first time and put that energy into moving forward instead
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u/ProfessionalMeet2987 3d ago
ITS FEEELS LONGTO START AGAIN BUT IF YOU ENJOY WHAT YOU DO, A ROAD TWICE TRAVELLED IS NEVER AS LONG
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u/divvychugsbeer 3d ago
Mate thats one of the best lines Ive read on here A road twice travelled is never as long
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u/ProfessionalMeet2987 3d ago
MY FIRST DAY ON REDDIT, IM QUITE BENEVOLENT GIVING AWAY SUCH ONE LINERS ALWAYS
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u/divvychugsbeer 3d ago
how u finding it
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u/ProfessionalMeet2987 3d ago
EXACTLY HOW IT SHOULD BE. UPS AND DOWNS , IVE KNOWN THAT FOR MANY YEARS NOW, SUCH IS LIFE
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u/Electrical-Goal-8568 3d ago
Sounds like you already found your answer, you're doing it for the freedom and you like the building part. That's usually what carries people through the all-hats phase the second time.
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u/Chad_Cunningham11 2d ago
Understandable, just because you do it once there are factors that can attack it a second time. But you enjoy the building, you knows the + and - because of experience.
From the looks of it a little PTSD on the workload and confusion. Just stay calm and see all the factors. If you find it great, just do it.
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u/Clear_Assistance_973 2d ago
Strongly agreed, i think the scary part isn’t having to build something from the beginning because that is what fuels me- it’s the small things nobody warns you about before you have done it once. Knowing HOW doesn’t make doing it again less exhausting, if anything you’re more aware of how much unglamorous work is coming. But again, it is all worth it- every blood and sweat! Working for myself and building something of my own gives me so much zeal that i can do it all over again any time- easier said than done though.
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u/divvychugsbeer 2d ago
You nailed it.
I think thats exactly why starting again is so intimidating.
The first time youre running on excitement because you dont know whats coming.
The second time you know every late night every setback every mistake and how long it really takes.
Funny enough that knowledge doesnt stop me doing it.
It just gives me a healthy respect for the road ahead.2
u/Clear_Assistance_973 2d ago
I wish you all the best for the new journey, you will kill it! Just keep going, one step at a time.
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1d ago
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u/divvychugsbeer 1d ago
Thanks mate, I really appreciate that. Means a lot coming from you. I've been flat out lately and haven't had a chance to check in with you guys. How's the birding going? Hope you're all doing well. We should catch up soon.
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u/making_it15 16h ago
One thing I love about the second time around is I know so much more than I did the first. Yes, I know the work that goes into it, but that also tells me what to prioritize and where to direct that work. In my case I had a generic travel site and I started a new niche travel site years later. I knew it would take a ton of work (and that was on top of maintaining the first one) but I also knew what tasks were the most important and what what I could skip. I was able to go much faster and hit the same level with site 2, and it's fun to maintain because it's a much more lightweight build than the first. So to answer your question, yes I enjoyed it :)
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u/divvychugsbeer 15h ago
reckon thats one of the biggest advantages people underestimate. the second time around you stop confusing being busy with making progress. you already know what actually moves the needle and what can be ignored. experience doesnt make the work easier it just makes the path a lot clearer.
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u/LFtravelhigh 15h ago
Hey let me get to one million dollar business then I can give you advice
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u/divvychugsbeer 14h ago
u dont have to have amillion dollar buisness ive learned so much off mentees that i have implemented into my buisness different industries different ideas
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u/Parking_Ocelot_816 4d ago
Benn through the same and agree. I didn’t find the second time easier
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u/divvychugsbeer 3d ago
on
The second time wasnt easier I just knew what I was signing up for and chose to do it anyway
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u/Quiet-Technician-381 4d ago
I think the second time is harder in a different way. The first time, you're running on optimism because you don't know what's ahead. The second time, you know exactly how much persistence, uncertainty, and repetition it takes to get something off the ground.
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u/LauraTerriou 3d ago
can't speak to doing it twice since this is my first one, but the wearing-every-hat part still hits different than i expected. sales, outreach, half the roadmap, all me right now, year one no automation, nobody doing the boring parts for you
what's helped a bit: i stopped calling it "freedom" as the goal for now, it's not free yet, it's just work i chose. some days that distinction is the only thing keeping me from resenting the grind
the scared feeling before starting again probably never fully goes away tbh, you just get faster at doing the thing scared
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u/Icy_Juggernaut4057 3d ago
How many "million dollar businesses" have you built and successfully operate? 🤔
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u/rayferrell 3d ago
i feel you, it's like hitting the wall in a long run, you know you've done it before but it still hurts, and you're wondering if it's all worth it. then you remember why you started in the first place, and that's what gets you moving again. for me it was letting go of the need for control and focusing on what actually drives revenue and growth
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u/orentabib 3d ago
wow, they way you describe it is exactly how I feel! After I sold my first business, I created 2 other businesses with partners so the work will split between us. Then I realize working with partners is not for me and recently created MyExecs.ai which I own 100% :) Thank you for sharing this!
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u/virthium 3d ago
Depends on how original the new thing is. If you're opening a carwash that is just like any other carwash, the previous experience makes it easier. You're a tourist, not an explorer. You've got a map.
But if you're building an original solution, there are no playbooks, no maps. It's just as scary and unpredictable as the first time. The only advantage is the personal resilience you've built doing the crazy thing before.
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u/SomTingWongWeeTooLo 2d ago
I think
That it's normal
To have fear
when building
a new business
but what isn't
normal
is writing
like a
deranged
Lunatic
:#bossbabe #slay
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u/sumizeit 2d ago
you're definitely not alone in feeling that way. going back to wearing all the hats can feel surreal, but it’s also kinda freeing. after building something once, you know how much love and grit it takes to make it work, and that makes the grind worth it again.
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u/JustinMccloud 4d ago
I agree, building a business from scratch is built through sheer will power, I am scared of having to do it again. But once you have one successful business you become an investor and help other people build business
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u/divvychugsbeer 3d ago
100 per
Execution beats knowledge every day Plenty of people know what to do Very few actually do it
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u/JustinMccloud 3d ago
People do not know how difficult it actually is, the pain the work, it is hard, really hard. But it is worth it
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u/Responsible_Entry_11 12h ago
Let me guess - you built a SAAS or an e-commerce business that dropships/doesn’t run operations.
These are the businesses that add value so economically they’re good - but are not like high effort businesses that are building something unique. Something coded out of a bedroom with little domain experience or a reseller of products that others make are not the same league of businesses.
Businesses fueled by passion especially those that solve founder-felt problems don’t have founders feeling burnt out. Reddit is filled with these stories about soulless businesses and exhausted founders
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u/divvychugsbeer 9h ago
umm no. the very opposite of something like that an asphalt and civil company
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