Why do I still feel broke even though the business is doing well?

★★ signal-medium r/smallbusiness · ↑ 85 · 💬 38 · 2025-11-30 · kw: any tool that · open on reddit ↗

Tool

Ramp

Issue

Business owner with $40k MRR suffers from scarcity mindset preventing necessary tool investments ($200/mo PM software upgrade rejected after 2-hour analysis despite acknowledging need), manually reviewing business checking account daily and expensing business costs on personal card to avoid guilt, underinvesting in growth tools and hiring due to anxiety about recurring costs.

Cost

$200/month × 12 = $2,400/year in blocked PM software upgrade; additional unstated opportunity cost from underinvestment in tools and people hiring

Recommendation

Ramp (for automated expense tracking and corporate card issuance); percentage-based profit allocation budgeting framework (set % for runway reserve and % for growth investments); weekly runway and margin tracking; ROI-based investment decision-making for revenue drivers vs. expenses

extracted with

anthropic/claude-haiku-4.5 · 2026-05-08

Body

I started my agency about 18 months ago and we're doing pretty well. We just hit 40k MRR last month but I cannot shake the scarcity mindset and it's starting to affect how we operate. Like I'm talking about obsessing over every single expense to an unhealthy degree. Last week my business partner wanted to upgrade our project management software to a plan that costs an extra $200/month and I literally spent two hours building a case for why we didn't need it (fun factwe definitely need it) I just couldn't handle the idea of adding another recurring cost. She was pretty mad at me and I fully understand here I just don't know the reason behind me being like this I grew up pretty broke and bootstrapped this thing on like 3k and now even though we're profitable and growing I still operate like we're one expense away from shutting down. I review our business checking account basically every day. I still use a personal card for a bunch of business expenses because I feel guilty putting them on the company card even though that makes no sense whatsoever My partner thinks I should talk to a therapist about it which honestly might not be a bad idea but I'm also super curious if anyone else deals with this? Like at what revenue point did you stop feeling like every dollar going out was a personal attack? Or does it never go away? The ironic thing is I'm probably COSTING us money by being so cheap since we're definitely underinvesting in tools and people because I'm too anxious about everything? Anyone has any tips on how to improve with the way I'm dealing with everything? Thank you

Top comments (8)

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[score=19] specialshi86

It sounds like you’re too frugal if you want to continue to grow. In order to grow, you should be expected to invest a certain amount back into your company. For me, I had to work hard to change my mindset on money. Budgeting was a huge help. I committed that a % of profits would be set aside for a rainy day, and a % would be invested in our continued growth. Whether it’s hiring people, adding to our tech stack, training, etc. That has helped as I have a set number to work with - and from there I prioritize investing in things based on the expected ROI. For example, If I add a tool for our team that saves everyone a few hours every week in admin work, they can spend that time doing something that helps our company elsewhere - like more work tied to revenue generation. If I hire someone that I can delegate tactical work to, it frees me up to me a multiplier for the company and focus on sales. It doesn’t mean I spend like crazy, but it really helped me having a set budget in the early days that was specifically tied to investing in our growth. Good luck!

[score=10] Full-Example-4912

It's normal. Growing up broke creates this feeling that doesn't just go away when you're actually 'making it' Here's what helped me: I started tracking our actual runway and profit margins weekly. Once I could see okay we have X months covered and we're growing at Y% and expenses felt way easier to handle. Dont get me wrong the stress didn't disappear but it got more manageable. Since you're suffering with expenses, what tool are you using? We have Ramp integrated within our company for expenses/cards which definitely helped since everything's automatic (automatic matching receipt and you can issue cards to everyone including yourself so that you can follow all the expenses way easier) Also your partner is right about the software btw. That $20/month probably saves way more than that in wasted time. At 40k MRR after 18 months you're doing amazing!! The feelings are valid but they're also lying to you a bit so relax keep calm and don't be scared of taking actions ;) Good luck!

[score=4] silesadelatierra

It’s hard to find a good balance between financial responsibility versus unreasonable penny pinching, both in your business and personal life. I believe there’s no amount of income that justifies financial irresponsibility, and yet nothing grows when you don’t feed it. I think the good news is that it’s easier for a tight ass to loosen up than it is to tighten up a loose asshole.

[score=3] PuttPutt7

I'm very frugal on EVERY expense. If not... Then money seems to vanish quickly. That being said. Realize there's is a difference between an expense, and a 'revenue driver'. Most revenue drivers still cost something, but if you can look at them from the outlook of "this will make me more money in the future, or save me X hours a week" then it's technically making you money. It's all about framing.

[score=3] Little-Set1246

Totally normal founder mindset. Growing up broke hard-wires you to stay in survival mode even when the business is fine. A bit of coaching or therapy helps rewire that so decisions come from data not fear.

[score=2] Majestic_Republic_45

I love it! Listen up, been in business 30 years with a successful service business. You keep doing what you’re doing. You will learn how to loosen up the purse strings a little. Immediately, we have to stop expensing things personally that are for the business. That makes zero sense. Think of it this way - you’re paying 30% more for any item u pay for personally that is for the business which should be in direct conflict with your mindset. Next - if it does not make me money, I don’t buy it. However, I will buy almost anything that makes me more efficient. You can say “that makes me money”, but I do it now to give me more free time because I am at a different stage in my business career. Free time is now worth more to me than money. AND pay for everything in CASH! Finally, you will probably never stop feeling the way u do. It’s what keeps a business owner hungry. I could have quit working 5 years and and I continue to work and provide the same level of service to my clients even though I could easily slack at this stage. I’ll do that until I don’t want to anymore. Good luck and you’ll figure it out!

[score=2] Original-Tune1471

That's actually a great mindset to have. Just need to fully realize needs vs. wants. Sounds like you got the not going anywhere near the wants down, so just try to think about what do you exactly need at that moment and will it affect business if you don't get it. In times of economic downturn like we're in now, cheapness is a great attribute to have. I save as much as I can and make sure to not spend a penny for the most part on my wants for the business, but only on needs. It put my restaurants in a great position right now with a lot of cash in the bank even though the restaurant industry has essentially tanked this year. In the future once you see your bank account get super fat, you'll relax a little bit by bit lol.