Sharing to just vent and to ask if anyone else has experienced this.

I (22F) am CTO & co-founder with my (20F) CEO. A year ago, we raised a pre-seed, and now we're raising $3 mill seed to meet client demand. We're in a legacy industry that is going through a crisis right now and adoption is good because of it.

It's been a bit over a month since we started meetings, and she called me today while I was napping (programming all-nighter) and confirmed we're oversubscribed, and I went back to bed.

I thought getting mainstream support would make me feel less stressed, but there's no relief. The idea of being responsible for losing $3 million is freaking me out. My cofounder and I don't come from money, and both had personal terrible things happen prior to starting this - so this is a very intense surprise. We also got a lot of pushback for both being young drop outs when our industry heavily trusts experience.

This is a good thing for us, but I know how much pain and work being a fast growing company is. Is this just what fundraising is after a certain period of time?

edit: muting this, but thank you to everyone for your responses. :,-)

I work for a seed stage startup in an executive role. Cofounders are opaque with the finances, but have assured us we have plenty of runway. Pay was 1d late on the last cycle and 4d late this time.

When I confronted our CEO about it, they said the person who was supposed to pull the trigger on the payday was on vacation so it didn't happen, but their first day back from vacation was the day we were supposed to be paid, and we still haven't been paid yet. fwiw we use Gusto for payroll.

I asked my CEO, well, shouldn't pay just be automated? and they shut me down saying this is just the way it is.

I get more and more demotivated every day it's late and nobody mentions anything. I have a team depending on me so I'd feel bad if I just stop working, but I also feel stupid working with no pay. I feel like I should be finding another job instead.

EDIT: fwiw I've asked the CEO multiple times if at least the other executives can be looped in our finances and have been denied. They view it as some kind of liability and privilege to know about our finances. They are novice founders.

I'm at the stage of seeking pre-seed funding to grow. I got a response to an email from a guy: We'll call him Jonathan C Miller. He invited me to meetings, explained how my company was going to be presented to the funding syndicate. Talked about other successful startups in my field that he had worked with. Name-dropped some big successes. It all seemed to be going well, so there were alarms going off in my head. I did some research on him - he has a handful of companies (we'll call them fytns group, fitness ventures, fitrepreneur, fitness syndicate) with websites, but the websites aren't great, and some of the links don't work (oh well, maybe he's not a details guy?). I continue to have the meetings with him and even added a suggested feature to my apps to show how fast I can ship code.

After a week of emails, whatsapps and meetings, he sends me some paperwork, and there it is - what it's all been leading up to: my up-front payment for his consultancy work. Unfortunately it wouldn't be legal [apparently] for him to defer the payment until *after* the funding is secured, although he can reduce it, and also has kindly offered to refund the fee if the funding pitch is unsuccessful [really? well that's ok then!].

I paid Crunchbase's fee and looked him and his companies up - he's the only employee & owner in each case and they all point to each other, and some weird crypto thing in Hong Kong. None of the companies he name-dropped mention him or his companies funding them. He then sent me a hilarious 'reference' email introducing me to the head engineer at Fitbit, and they replied (from their Hotmail address!), advising me to work with Jonathan, but they couldn't talk because they were just getting on a plane to a 'retreat' in the Phillipines.

So now I'm back to sending cold-call emails to angels and VCs, and feeling rather deflated and humiliated, but at least I'm not also down $2500.

Remember - if it sounds too good to be true, it probably is. Do your research and don't part with cash to 'release funds'!

Edited for the avoidance of doubt

Wanted to share for me the bootstrapped person/startup that inspires me: Ben Chestnut bootstrapped Mailchimp from nothing and sold for $12 billion cash.

This and many other similar stories pushed me to bootstrap my projects rather than seek venture funding.

Last week, he officially left the company.

Here's how he pulled off the best bootstrapped exit of all time:

1) Mailchimp founder Ben Chestnut learned about small business from his mom, who ran a hair salon from the family's kitchen in Georgia.

From an early age, his future would lie in the creative industry.

He studied physics at the University of Georgia and industrial design at the Georgia Institute of Technology.

He still lives there to this day.

2) His first job was as a designer at Cox Interactive Media.

But he got the entrepreneurial itch and started a design agency with his friend Dan Kurzius in 2001.

They quickly realized they were sending clients emails, but there wasn't a good tool on the market for this.

Mailchimp was born!

3) One of the great advantages they had as designers was well..they could design.

And they also realized while there were new email marketing competitors, none had design chops.

Mailchimp grew quickly from its quirky design and memorable monkey mascot.

In the 2000s, Mailchimp invented the 'freemium' model, which became the most popular Internet business model.

After introducing freemium, their profits increased 650% in one year, and their total users went from 85k to 450k.

4) It wasn't all plain sailing, however.

Chestnut stepped down as CEO of Mailchimp after arguing in a leaked email that asking for pronouns at the start of meetings “does more harm than good”

What Ben did next was shocking but also perfectly reasonable: he sold.

5) Mailchimp was sold to Intuit in 2021, 20 years after its founding, for $12 billion in cash.

The buyer? Intuit isn't a widely known brand, but it owns Quickbooks and other popular small business software products.

Here's Ben explaining why he sold:

Ben and Dan each retained 50 percent ownership of the company from inception, which was a feat in and of itself with virtually every other company raising venture capital.

If this was the case at sale, Chestnut likely walked away with north of $5 billion dollars.

6) Not bad for a side project.

Today, Mailchimp is still the world’s leading email marketing platform, with a staggering 60 percent market share — more than 16 million people use it to power their email marketing.

You probably read emails powered by the software every day.

Mailchimp's story goes to show there's many paths to success and you don't really need to sell off parts of your company to raise capital.

About a year into building my app as a 1st time, non-technical founder, I became frustrated with the progress of the team I hired.

Mainly it was the slowness, amount of bugs, and I started to notice some of the bugs were backend issues which scared me. I thought maybe the app looked pretty but was crap under the surface. The team that built this was an Indian dev shop team, and the total spent was about $25k.

I decided to make a switch from that team to an American who was more startup & MVP focused. It has now been another year since I hired him. Since then the speed of progress is about 30% of the original Indian team, the scope of the app was gutted and now is about 40% of what it was, and the cost is 10 times…yes…an order of magnitude more expensive.

I’m just super frustrated at this point. I feel like returning back to the original Indian team. It’s just not worth the cost I feel like.

I’m completely taking it on faith that the app backend is somehow bulletproof under the surface. Yet…there are still bugs, the app is still a shell of its former self, progress is unbelievably slow, and I’m just totally demoralized.

What should I do? Like if I can’t make determinations on the codebase itself, how am I supposed to evaluate if this American developer is worth it?

The hard part is I like him on a personal level, but he’s just unbelievably expensive.

I'm a final year Computer Engineering student, hence applying for jobs all around. There's this particular trend I've noticed with startups that are coming up these days. That is, even for the absolute basic stuff they'll use 'AI', and they'll think they built something 'revolutionary'. No. You're breaking your product in ways you don't realise.

An example, that even some well established companies are guilty of: AI Chatbots

You absolutely don't need them and it's an entire gimmick. If you really wanna implement a chatbot, connect the user to an actual person on your end, which I think is not possible if you're at a 'startup' stage. You'll need employees who can handle user queries in real time. If the user really is stuck let them use the 'Contact Us' page. A really close relative of mine is very vocal about the frustration he faces whenever he tries to use the AI Chatbot on any well known e-com website.

The only case for AI Chatbot that makes sense is when it's directing the customer to an actual customer support rep if none of the AI's solutions is working for the customer. Even then, implementing a search page for FAQ is extremely easy and user friendly.

Another example: AI Interviewer

I recently interviewed for a startup, and their whole interviewing process was AI'zed?!?! No real person at the other end, I was answering to their questions which were in video format. They even had a 'mascot' / 'AI interviewer' avatar designed by an AI (AI-ception???). This mascot just text-to-speech'ed all the questions for me to rewind and hear what I missed again. And I had to record video and audio to answer these questions on their platform itself.

The entire interview process just could've been a questionnaire, or if you're really concerned on the integrity of the interviewee, just take a few minutes out of your oh-so-busy schedule as a startup owner. Atleast for hiring employees who would make the most impact on your product going ahead.

I say the most impact, because (atleast as a developer) the work done by these employees would define how robust your product is, and/or how easily other features can be integrated into the codebase. Trust me, refactoring code later on would only cost you time and money. These resources would rather be more useful in other departments of your startup.

The only use case for an AI Interviewer I see is for preparing for an actual interview, provided that feedback is given to the user at the earliest, which you don't need to worry about as a startup owner.

So yeah, you're probably better off without integrating AI in your product.

Thank you for reading.

TLDR; The title; I know AI is the new thing and gets everyone drooling and all, but for the love of God, just focus on what your startup does best and put real people behind it; Integrating AI without human intervention is as good as a broken product; Do your hiring yourself, or through real people, emphasizing on the fact that the people you hire at an early stage will define your growth ahead;

I searched the subreddit and found only references to Taleb from 8-9 years ago, so I wanted to re-up the conversation.

His Incerto series (Fooled by Randomness, Black Swan, AntiFragile, Skin in the Game) hits on the themes of randomness and, specifically, what I think of as "the structure of chaos." The future is fundamentally unpredictable and random in ways that fool even the most intelligent statisticians, forecasters, and entrepreneurs.

If I could boil down my biggest learnings from this series, it's this:

• Every massively successful startup is fundamentally lucky. They did not strategically optimize every decision to achieve success - they only think they did because of postdictive narrative building. They were fooled by randomness.
• If you understand the structure of randomness (specifically, what Taleb calls Mandelbrotian "Black Swan" randomness vs. Gaussian "normal" randomness), then you realize that *someone* has to occupy the long tail positions at the upper and lower distributions - but the people occupying those positions have no more choice in the matter than you or I do.
• You can do all the correct things and still fail. In fact, this is the most likely outcome by far. But if this is true, then it relieves a ton of the pressure that comes with trying to optimize every decision and minute of your day, all the time.

We still have agency. We can still materially impact our customers and the direction of the business, but it's more a question of exposure: how do I limit my downside risk to acceptable levels while exposing myself to as much upside as possible?

Everything else will happen as it happens.

However, this DOES mean we can quit listening to gurus, reading business help books written by MBAs, or listening to endless podcasts from entrepreneurs and VCs with survivorship bias (I'm guilty - having done all these things). Every startup will succeed or fail in its own unique, unpredictable, and completely inimitable way.

Twice recently, I've seen posts on her slagging Stripe. They used similar arguments against Stripe. This morning I decided to do a little digging to see whether something else was going on. Sure enough, it lead me down a rabbit hole of sock puppets and self-promotion.

Today's post was put up by u/Radiant_Alana and a very quick look into their post and comment history leads to a very quick conclusion that this person's anti-Stripe stance is based on the fact that they're the founder of OpenPay.

Or, are they? because that's what's been claimed by u/Strange-Device4359, u/Maleficent_Code7254, u/Xak2020, u/ankit77, and u/Serenity_Radiate as well as another now-deleted account.

All of these accounts are sock puppet accounts whose post and comment history show that the folks behind OpenPay are shady af.

I don't do business with shady people and think that these accounts should be banned from this sub.

Edit: Added u/Serenity_Radiate thanks to QuackDebugger for finding that one.

From the first thought 3 years ago, to go full-time into my project 1,5 years ago, I finally achieved market access in a highly regulated industry. It is a promising business, we got a great team and support. And first clients.

I feel very emotional about this moment, proud, exicted of what to come, a bit afraid, happy, exhausted and a lot more. It was hard, dedicated work, I wouldnt say stressful as I always had a goal in my inner eye and now I look towards the next 2-3 years where I can make this business grow.

Being a founder is great, I would do it almost the same again until this point. This is all, I just wanted to share this milestone. Have a great weekend!

True wealth will often come from creating value for others.

Instead of trying to chase after quick money, focus on building products or services that make other people richer.

This approach works because:

• When you help others become more successful, they're willing to pay a anything for what you offer
• It creates a win-win situation where your success is directly related to your customers success

Examples:

• Shopify: Gives businesses a platform to easily set up an online store, which helps them make money online
• Stripe: Simplifies online payments, which makes it easier for businesses to accept money from customers worldwide, helping them become more successful
• Coursera: Offers courses and certifications helping people get more skills to advance in their careers

When you can demonstrate a clear return on investment, pricing becomes less of an issue.

Do you agree with this approach?

TLDR: CTO. The feeling of being "2nd" in my own startup is eating me up. How do other CTOs handle this feeling?

Recently watched the video on co-founder selection which came from YC. There was one particular line which stuck with me, "The startup is bound to fail if both co-founders want to operate as a CEO." Also, The CEO is bound to be the face and become famous once the startup becomes famous.

We are two co-founders building in e-commerce + AI field. I am coming from a tech + domain background with heavier tech focus while my co-founder comes from domain + tech background with more experience on domain. Based on the discussions, we decided to split 50-50 equity and I lead the tech role, become the CTO while he takes up the CEO role. Both of us started from scratch here. IMO, I had a slightly higher opportunity cost where I left a really high paying job while my co founder had a comparatively lower salary. But, this could just be my bias.

Now, the problem - sometimes I feel he tends to behave a little bossy assuming he is the "CEO". This creates a feeling in me that I am the 2nd person in my own startup. All the LinkedIn posts, all the talks where we represent the company, he tends to be taking the lead while I am sitting there assisting. I want to speak more, but do not want to step on his toes, so finally just tend to the be supporting him.

He feels everything is going well, but this feeling of being forgotten for the startup I built with an equal effort has been eating my brain for quite a few months. I thought about bringing up this topic, but I have no clue if there are any solutions here.

I know some folks do not want to come to limelight so are happy to be a CTO in the background. But, I do not. Just because we decided to choose random titles, I do not want to be left behind. I want to be part of the fame which my co-founder is a part of.

Am I overthinking here ? Do other CTOs get the same feelings ? How do you guys overcome it?

“We’ve raised $6.6B in new funding at a $157B post-money valuation to accelerate progress on our mission. The new funding will allow us to double down on our leadership in frontier AI research, increase compute capacity, and continue building tools that help people solve hard problems," read the company’s blogpost.

The closure of these funds follows the resignation of Mira Murati, Chief Technology Officer. Mira Murati announced on Wednesday that she has resigned from OpenAI after more than six years there, most recently as its chief technology officer.

"After much reflection, I have made the difficult decision to leave OpenAl," Murati wrote in a statement on X. "I'm stepping away because I want to create the time and space to do my own exploration."

I built a startup years back it meant to seamlessly organize large group events and hangouts. The issue I faced with it was although we reached close to 1000 users I couldn't get it viral in time before I received the letter from FINTRAC to cease and desist since its fintech.

Anything I can do with the code I built over the years? Our algorithms were quite fascinating (my opinion) we leveraged insights from the automatic trading logic to make it such that you can use rule based logic to accept going to an event and then it all worked automatically based on the rule (min group size etc.) after that you receive notification if this thing is happening or not based on the rule.

Our goal was to use ML to identify social networks you have (the different groups you hang with) and what you guys like to do then start making suggested plans automatically that are seemless.

Edit: Thanks for the amazing feedback and insights and connections. Its clear to me now that the only potential buyer for this is someone who happens to be interested in starting the exact same thing (unlikely), so they run the platform as is just execute it better and get it for a small fraction of the cost and time to build new. I also received lots of interest in joining other teams of startups in similar space, I am thankful to all. I just don't want to do this in B2C model anymore.

The startup has been around for 3 years and is currently making $1.6million ARR. They are also in late stage conversations with a VC firm for a $7m fundraising round for 20% stake in the company. The founder and current CTO is offering me a role as co-founder and CTO with an annual salary of ~$100k. However he is asking me to pay $20k up front before joining for my 5-15% equity stake in the company. Is this normal?

We are located in the United States

Let me guess, you've probably applied to startups and gotten rejected... or wondered if it's unattainable if you're not from San Francisco or used to work at Apple. The truth is, great startups are picky. They have to be.

But if you're a great candidate whose career is more of a winding path than a straight highway... I feel you.

I don't have a perfect resume: No Ivy League/Stanford, no FAANG job, I don't live in San Francisco... but last year I wrote an insane application that got me a job I can safely say has been a dream job so far.

Here's what I did:

-I researched the company like crazy, signed up for the product and studied the job description in detail

-I created an artifact as if I already worked there. I'm in marketing so I wrote an article - complete with SEO research and social media images (SEO and social media skills were mentioned in the JD specifically).

-I used a bunch of their widgets on my website and created a separate page to the application

-I sent it to them

The next morning, I woke up to an email saying: "Incredibly impressed with so much of what you've done here. I think you may have ruined applications for this type of role for me forever."

3 weeks later, I started at the company and have just celebrated my 1 year anniversary. If you want to join a great startup, here's the advice I'd give you:

15 minutes or 15 hours

If you want to stand out, there are 2 ways (besides a perfect resume): Spend 15 minutes recording a Loom video giving the company ideas/feedback. This will set you apart from 90% of candidates. Or spend 15 hours crafting something crazy — like I did. This will set you apart from literally everyone.

Send over an artifact

I once heard "The best way to get the job is to do the job before you get the job". This is absolutely true. If you just act like you already have the job and send the company something you made, your chances will skyrocket:

They see that a) you can do great work and b) you're proactive — both of which are generally valued in startups.

Research DEEPLY

Read 10 blog articles, maybe 20... The more obscure, the better: People will be impressed when you reference facts and things themselves may have forgotten. Try the product — pay if you have to.

Especially at startups, this will familiarize your name. And it'll shorten your on-ramp time, which makes you an even better candidate.

It doesn't take much to become a way better candidate than the hordes of people blindly dumping their resumes into someone's inbox

At 18, I really didn’t see myself getting into business later on.

If I could chat with my younger self, I’d definitely say:

Stop worrying about what everyone else thinks. Just get into what you love, try new things without fear, and always go with your gut. Remember, it's the risks we skip, not the ones we take, that we usually regret.

In a shocking move that's sending ripples through the tech world, Matt Mullenweg, the founder of WordPress, has just banned WP Engine, one of the world's largest WordPress hosting services, from the WordPress ecosystem.

This decision has ignited a firestorm of speculation and debate, with supporters praising the move, while critics decry it as a heavy-handed abuse of power.

This illustrates to me just how much power lies in the hands on one man.

I am young entrepreneur, still figuring out the entrepreneurship situation, not a complete newbie and have built some products and made some money, but fairly new to this game.

Throughout this journey, the BIGGEST problem I have faced is find the right people to TRUST and work with.

I have been cheated and betrayed by people so many times, now I have seriously started to think, why is it always me : (

From cofounders ghosting to cofounders literally running away with my money to clients screwing me over, I have seen it all and have grown up to learn from those mistakes and not to repeat them. I have seen multiple betrayals and people changing after money is on the table.

Would love to know something about your journey of betrayals and cheating that you have faced in your business life.

Everyone loves this mantra, and Paul Graham's essay on it. But have you ever seen it gone wrong? More often I've seen startups struggle with applying it and actually things manually, than overdoing it. But:

• I've seen a startup that have held onto the non-scaling aspect too long before they realised it was that thing that they couldn't scale (inhouse delivery).
• A startup that in building an MVP went overboard on very basic tech stuff such as a database, trying to be lean but the dev had non of it.

What have you seen?

Hello reddit community 😁

I am part of a small team working on our own startup and trying to understand the real struggles of product validation and finding product-market fit (especially for tech founders). We know that often times, founders get their hands dirty with programming and building the “next big thing” without proper research beforehand, therefore they fail😐

If you’ve faced challenges getting your product or service ready for launch, I’d love to hear what worked (or didn’t) for you.

Here’s what we’re curious about: - What were the biggest challenges you faced when launching your product? - How did you overcome them?

Thanks and best of luck to everybody 🚀

this isn’t targeted towards anyone so keep reading or don’t… idc

beyond the AI hype, the not so complex industries/solutions (whatever that might be), and the need to work on shiny objects, lay great opportunities for massive businesses.

I have worked in manufacturing as an engineer and encountered many problems that can be solved with technology. I have investigated opportunities within supply chain, healthcare, defense, and pharmacy management. From my conclusions, there’s definitely great opportunities for the ones who are willing to deliver solutions to the deep rooted problems within these industries.

to give an example, there’s a major demand for skilled machinists within all sectors manufacturing. At my previous job, we had about 12 machinists running 12 machines. Imagine the cost associated with that. Now imagine automation reducing the number of machinists needed by automating some of the tasks.

Imagine if you could predict drug shortages using pharmacy data? Imagine if you could increase visibility within the supply chain by leveraging data, determined bottlenecks, and reduced costs?

too many smart people seem to be working on things that do not deliver much value. Seriously, how many damn AI assistants do we need? Go beyond the shiny objects and dig for the gold.

Hey folks. Just wanted to get your input on an offer i've been extended.

For reference, the startup has no MVP, 0 outside investment whatsoever yet. All the founder has is a simple demo of what he thinks it would look like. Basically, a glorified wireframe.

I have been offered 10% equity to be a partner, with me "eventually" being the CTO. This offer to me seems like a slap in the face... I stated that, given I would be the one completely building the tool from the ground up, that I should be the CTO cofounder and should be given something like 30-40% plus a market rate salary once some milestone is hit (investment of X amount or revenue of X amount or profit of X amount). I didn't come up with these numbers on my own but scoured the internet on what is fair and even went conservative.

He claims "You wouldn't be a cofounder, but you'd be a partner with the ability to transition into a CTO role". How would I not be a cofounder given I would be the one building the entirety of the tool for MVP/hopefully initial investment while he would be the one being the face of the company doing the marketing? He claims he already has a vc lined up at 7% for 500k. I find this incredibly hard to believe as this is nothing more than an idea and a glorified wireframe at this stage.

Am I insane?

Edit: what would you expect to be a fair deal, given the infancy stage of the startup?

I’m a software engineer with 17 years experience in the financial industry. I am going to startup a software company. I’m looking for an individual to partner with to brainstorm ideas, and bring our idea to market. This individual should be self motivated, and have experience in the software industry as well. Thanks!

What do you do with your sleepy startups?

I have a lot of abandoned projects, either because I didn't do the marketing, or because I don't like them anymore.

So I decided to create a solution to try and sell these projects.

Even a small amount doesn't matter.

ALL built projects have value.

And if you're not going to exploit that value, you might as well sell it to someone who will be motivated to do so.

I thought it might be a good idea to create a microacquire of failed or sleeping startups.

Anyone can list their projects, their startups, their side businesses...

What do you think of it?

What are some standard rejection lines/signals from VCs during fundraising? I've mostly heard "It could be a great business but we're not sure it's venture scale". What else do you get?

Any hard "No"s? :)

What if the VC says the above, and yet asks for more details to send to them in closing?

Just practicing pitching now, and learning to read signals. Any pearls of wisdom welcome.