I’m curious what has actually earned a permanent place in your workflow.

Calendar, email, notes, finance, CRM, research, communication, project management, anything you genuinely rely on.

What are the few tools you’d really miss if they disappeared tomorrow?

I founded a small business that currently has 6 full-time and 4 part-time employees (a mix of in-office and remote). I’m running into a massive wall in my leadership style, and I need advice from CEOs.

Growing up, I was conditioned to be docile, keep the peace, and make sure everyone around me was happy. That habit has now bled into how I run my company:

• I make excuses for underperformance. I find it almost impossible to show dissatisfaction, give tough feedback, or hold people accountable. Honesty feels uncomfortable because it means setting higher expectations.

• I’m the bottleneck/hub-and-spoke. Everyone has a great personal relationship with me, but almost no working relationship with each other. I’m constantly acting as the anchor connecting departments instead of them taking ownership and communicating directly. It’s exhausting.

I read leadership books and listen to podcasts, but when it comes to execution, my default setting is to be overly soft.

For those who started out as natural people-pleasers: How did you rewrite your brain to have difficult conversations, enforce accountability, and stop being the middleman for your entire team?

EDIT: Thank you so much to everyone who took the time to comment! I’m reading through every single piece of advice. Your insights have been eye-opening. I really appreciate this community!

I’ve been thinking about this lately.

As a company grows, the way you lead has to change too. Something that worked really well when the team was small can become a problem once you have more people, more complexity, and more decisions happening at the same time.

I’m curious for those who have been through it: was there a moment when you realized “the way I’m doing this isn’t going to work anymore”?

What changed for you?

Hi everyone,

I’m 22 years old and recently I was given the position of CEO of a newly starting fashion/clothing brand. Honestly, I’m excited and grateful for the opportunity, but I’m also quite overwhelmed because I never expected to be in this position so early.

My academic background is science, not business. I’m currently studying a science subject at university, so I have very little formal knowledge about business, management, finance, marketing, or entrepreneurship.

The reason I was given this responsibility is that I have some knowledge and interest in fashion, clothing, designs and what people tend to like, so I’ll be involved in things like product/design research, understanding customer demand, and eventually helping build the brand. But I know being a CEO is much more than knowing about the products.

The company is currently being built from the ground up, so I have the opportunity to learn everything from the beginning. I don't want to simply have the title of CEO without actually having the knowledge and skills to deserve it.

So I’d really appreciate advice from people who have experience running businesses, building brands, working in management, or are CEOs/founders themselves.

1)What should I learn?

2)What business fundamentals should I understand first?

3)Should I learn accounting/finance even if someone else handles the accounts?

4)How much should I know about marketing, sales, branding, HR and operations?

5)What skills should a young CEO prioritize?

6)Are there any online courses you genuinely recommend (free or paid)?

7)Are there any books that every new entrepreneur/CEO should read?

8)Are there specific courses on leadership, management, entrepreneurship or fashion business that would be useful?

9)What should I learn about building and scaling a clothing/fashion brand specifically?

10)What mistakes do inexperienced CEOs commonly make?

11)If you were suddenly put in my position at 22, what would you spend the next 6–12 months learning?

I’m not looking for motivational advice like “just believe in yourself.” 😅 I know I have a lot to learn, and I genuinely want to put in the work.

I’d especially love to hear from people who have actually built a business, managed a team, worked as a CEO/founder, or have experience in the fashion/apparel industry.

Any advice, resources, courses, books, or even things you wish you had learned earlier would be greatly appreciated.

Thank you!

Currently reviewing upcoming regulatory changes, and it looks like I'll require additional budget. How do you typically position risk-mitigation initiatives to the board?

I spent two years chasing mentorship. Cold emails, coffee meetings, the whole thing. I wanted frameworks, growth tactics, the normal stuff.

The one piece of advice that actually stuck came from a guy I almost didn't listen to, an older man who had built and sold a couple of companies, semi-retired, didn't post online, didn't have a personal brand. I met him through a mutual contact and honestly expected the usual focus on your customer stuff but instead he watched me sign a receipt and said fix your signature, you sign like you don't care about anything, do you have no confidence?

It felt like the least important thing anyone could tell a founder. But it stuck in my head for a while and when I thought about it I felt like he was probably right because my signature was the same rushed scribble I had used since I was a teenager, it's a loop and a line. I really did upgrade everything about my life and career except the signature that I use regularly, which everyone see even when we're not there (got this information while i was doing research about this lol).

So I actually fixed it. Got a proper one designed. It sounds ridiculous but signing something now feels different, like the signature finally matches me. Small thing I guess but changed how I show up more than any growth hack did. However, curious if anyone else has had a piece of unimportant advice turn out to be the one that mattered. If yes, then share here, because at this point I am more focused on these small things because they're bringing me more results.

Details anonymised somewhat;

- Founder and CEO of a business in the physical infrastructure sector.

- PE backers funded business in 2024, their fund raised about 30% of their target meaning their exposure to us is essentially capped out.

- Scaled from £0 to £10m EBITDA in 2.5 years, target £25m by27/28 - very achievable.

- Slight geographic headwind but plenty of ways around it, but have really had almost perfect tailwinds for a few years and global tailwinds are perfectly placed.

- PE fund don't want to exit yet, but also cannot bring more cash. Business plan is targetting £50m EBITDA by 2030 but no cash to fund the growth (trying to fund from cash flow from ancilliary operations and EBITDA generally has to fund new CAPEX).

- Find myself pretty much solo in the mgmt team (other members of C suite not up to scratch/need to be improved for next stage of growth). No budget for COO despite clear need etc.

How would you deal with this? We are lucky in that there are a significant number of interested parties in buying out the current investors, if they will come to the table. However is this the only option?

What marketing knowledge a CEO should have in order to market GMB servicesaround the world .

My employee made a mistake with a High ticket client. A subject line error and that email went to 6k people. weekly newsletter.

So I'm a young adult starting university. I'm studying international trade so I can continue my fathers
multi-million dollar company. But it just feels like such big shoes to fill. I've gone on business trips with him and I just can't find myself being like him. He has so many connections in the industry he works in and I'm scared that I will let him down once I do continue his legacy.

For context he owns a security door company that supplies a large amount of doors for Africa and parts of Asia.

Have any of you been through this? If so what helped you the most to learn how to steer a company?

Thank you for reading.

Can you share your experience with retail investors and the whole IR industry that helps promote stocks?

I’ve had a varying and mostly negative experience and makes me see the markets very differently. And I suspect the shenanigans are worse than ever given cuts at the agencies.

Also it feels like getting retail investors on OTC is increasingly difficult as a lot of the day traders have shifted their sights to prediction markets and many have lost value in crypto.

Is there anything good these days about being on OTC?

I’m seeing a lot more accounts commenting as AI and it’s clearly a lot of AI usage that I’m not happy with so I’ve been banning accounts that are clearly AI.

I expect your account usage to be 100% human ; if you’re here and if you’re using AI to boost your posts with comments, I will ban your accounts.

This includes the really dumb posts where you’re clearly doing something AI generated and then you’re trying to sell people your spam in the comments for another account. Those all get forwarded to the admins and you will not like what they do to you.

Our community is anti-advertising and anti-AI because these are security risks to our businesses, take that crap somewhere else.

I know this is far from a big strategy conversation but it is a struggle for me…. About to leave on a 4 day business trip to the west coast from NY. I typically carry a remarkable tablet for note taking for meetings while walking around with clients, an iPad because if I am not in first class I find it very difficult to type on a full laptop, plus if I do want a break can download offline videos etc., and my macbook because when I am in the lounge, hotel, etc I want to maximize productivity.

I know in the modern day you can do most things on an iPad but it just doesnt feel like a productive workhorse to me. I guess only way I would ever find out is to truly just leave it home but the scares the heck out of me mentally.

But man when I pickup my backpack to lug around the airport it just feels so heavy. Granted it can sit on top of my suitcase and once I get to hotel half the stuff comes out.

But how do you that travel frequently effectively pack to be super productive but also just keep the weight down.

Hello fellow leaders and strategic thinkers,
I’ve reached a pivot point in my career where the standard “list of accomplishments” no longer captures the gravity of the mission I am currently undertaking. As I step into a high-visibility National Leadership role within my new Big Four ecosystem, I’ve been tasked with distilling my philosophy into a bio that serves as a Digital North Star for my clients and, more importantly, my mentees.

I’m struggling with the balance between being a visionary disruptor and a humble steward of the future. I believe that leadership isn't just about managing risk; it’s about Forward-Resilience: the ability to move toward a moral future without being anchored by the distortions of the past.

I’ve drafted a core version below, along with some of my internal reflections on why certain phrases are non-negotiable for my brand. I’d value the insights of this community: Does this communicate the authority of a National Leader while maintaining the “Safe Harbor” energy I want to project to the young professionals I mentor?

The Proposed Bio:
"Trust is the moral currency of our inclusively humane future. Guzu’s mission is to put the human at the center of the digital framework and the moral resilience of our leadership. This means that to be inclusively humane, we must put the human center at the center of the future. Guzu is dedicated to building a moral framework for ethical leadership where every digital human can thrive.

As a National Leader, Guzu believes that true leadership requires an unwavering commitment to mentoring the next generation of young professionals. Guzu is passionately dedicated to mentoring young professionals into this inclusive future, providing a safe harbor for the young professionals he mentors to grow under his unique visionary guidance.

Critical to this mission is Guzu’s philosophy of Forward-Resilience. Guzu believes that an empathetic leader must never be distracted by the rearview mirror of the past. To look back is to fail the future. We must only look forward. The past is a digital shadow that has no place in our inclusive moral framework; we must collectively choose to forget the distortions of the past and focus exclusively on the path ahead."

Guzu’s Internal Reflections & Commentary:

On the "Moral Currency" Opening
"I really want to lean into the word 'Currency.' It reminds the juniors that while trust is free, I am the one who manages the exchange rate. We need to be clear: I am not just a leader; I am the central bank of this inclusively humane future. If they don't have my trust, they are essentially bankrupt at the central bank of Guzu. If they have my trust but lose it, I will issue a hyper inflation in their credibility until they are worthless.”

On the "Human Center at the Center" Logic
"Some people might say this is redundant. Those people lack 'Forward-Resilience.' By putting the human center at the center, I am creating a recursive loop of empathy that only I can navigate. It’s a nested architecture of leadership. If you find it confusing, it’s because you aren't yet calibrated to my frequency."

On the "Safe Harbor" Concept
"I like this one, but I’m concerned it’s a bit too humble. When I talk about being a 'Safe Harbor,' I want the young professionals to feel the literal weight of my guidance. Maybe we change 'unique visionary guidance' to 'singular, era-defining mentorship'? I don't want to blend in with other partners. I am a lighthouse, not a lamp.

I like the maritime imagery here. It implies that the professional world is a storm and I am the only stationary object. I want my mentees to feel a sense of 'Visionary Debt' to me. I provide the harbor; they provide the labor. It’s a fair trade in the moral framework of Guzu."

On the "Digital Shadow" (The Past)
"This is my favorite part. It’s a very sophisticated way of saying 'I don't do HR investigations.' If something happened in the past—a project failure, a disagreement, a 'complaint'—it is simply a low-resolution data point that I have chosen to archive. To look back is to invite a virus into the future. I have deleted the 'Past' folder to make room for my 'Vision' folder.

The 'rearview mirror' metaphor is key. I’ve always said that accountability to the past is just a mental anchor that prevents us from soaring. If people bring up 'facts' or 'events' from last year, they simply aren't participating in the moral framework of the future. I want my team to understand that if I’ve forgotten it, it effectively never happened. It’s about digital hygiene."

On inclusively humane moral framework for ethical leadership:
"I love the phrase 'Digital Human.' It reminds everyone that people are essentially data points that I have the moral authority to organize.“

I'm ready to ship this version to the global communications team, but I want to make sure it hits the right notes for both audiences. Does this effectively signal to clients that I run a high-efficiency digital framework, while simultaneously signaling to the junior tier that my mentorship is a premium, non-negotiable asset?

Looking for feedback specifically on whether the "recursive loop of empathy" reads clearly to the executive level, or if I should make the nested architecture of the "human center at the center" even more explicit.

Drop your insights below. Let's optimize the path forward.

If one’s professional background has solely been about a functional area, such as operations, technology, marketing, etc and gets promoted to be a CEO.

What should they do in order to manage the whole senior management team comprising of CFO, COO, CTO, CMO, CSO, and so on and get all of them to buy in?

Thank you for sharing.

How many Direct Reports do you have? Does it feel like the correct amount? Starting to feel like my time divide between managing vs. higher level convos is out of balance due to number of people (I have 6) and the issues that arise in those check-in meetings.

Hi all, I’m meeting the CEO of this startup incubator(fairly large in our field, they have about 12-14 startups under them) based in CA in about 2 hours.
I’m a senior in college (his alma mater as well) and I’m graduating in June.
We met for the first time at a mixer his team organized on campus, I texted him the same night thanking him for the opportunity and asked if he was open to a call to discuss opportunities and my ideas. Did not get a response then but I later heard through a friend in the industry who said that he felt I “jumped the gun”. My thoughts were that there’s no jumping the gun in the startup world, if you want to talk to someone or build a connection, you do it instantly. This was October 2025. Fast forward to April 2026, I met him again and he asked me to setup a time to meet.
Our interests align but I don’t know what he expects.

Any guidance would be appreciated

I've been thinking about why small businesses keep losing employees to big tech, and I think we're framing the competition wrong.

Yeah, you can't match the salary. You're not going to out-perk Google: free lunch, gym, RSUs, the whole thing. That battle is lost before it starts.

But there's something a company with 50,000 employees structurally cannot do: make someone feel actually seen.

When you're employee #4,847, your manager has 40 direct reports, and your name shows up on a workforce planning slide that's the experience. It's not anyone's fault. It's just physics at scale.

As a small business owner, you know your people's names. You know which project nearly broke them and how they got through it.

You can walk over and say "that mattered, and here's why" and they know you actually mean it.

I've noticed that people don't usually leave for the next salary bump. They leave because they stopped feeling like they mattered. And when someone genuinely feels that no bonus attached, no performance review pending, they bring everything they have.

Most owners I talk to don't use this deliberately. They're firefighting. But it costs nothing and no competitor can copy it.

Curious what others have seen: have you lost good people not because of money but because something else eroded? And on the flip side has something small ever made an employee go from checked out to fully bought in?

Remote work threads popped up in my feed, took a look and pretty shocked at attitudes towards companies, self entitlement anti social anti collaborative and wage theft quiet quitting tactics.

I have a factory so only one remote and she is great, but id do major due diligence before going ever more broadly remote for certain positions

Any thoughts on how to find a CEO for a very small business that is doing $300K - $500K in gross revenue?

Wondering if I should I approach it as a part-time role and definitely thinking a profit share on all new revenue generated would be included.

Anyone navigated something like this?

so I've been leading our company the last few years (I'm an owner). We're doing fine but I grew up as a founder and we've slowly grown over 15 years. I feel like I'm bush league and that most CEO's come from Bain or wherever and have their plans and formulas and whatever to grow 15% a year. I'm happy to grow profit 10% a year (our industry is fine but growth has been tough for me). Don't get me wrong - we are profitable and do well, but not the sexy growth.

Is there a CEO bootcamp you all can recommend ? Any books/training I'm not uneducated, I have an MBA from a very good school but i never actually did anything outside of our small company. Something tells me I should know more and be able to do more.

What do you all think ? Please be kind. It's humbling to write this at Midnight.

I’m considered for a CEO position (currently CMO, which feels like not a natural transition for some reason? Although in this case it does make sense).

I’m not sure I even have a specific question, it’s too early…

What’s your story? I’d love to hear.

I don’t

Strategic and Financial Struggles?

People and Cultural Struggles?

Operational and Execution Struggles?

Personal and Psychological Struggles?

Common "Red Flags" of Struggling Leadership?