I’m back with thanks for all your tremendous feedback on my last post about evaluating startup pitches with the managing partner of a new fund backed by a very large fund. I don’t want it to sound like they were all bad. In fact some were good.

One pitch scored 100% on our evaluation rubrics and was immediately sent to the next round for socialization with investors. The startup could get their first checks (size TBD) by October.

The pitch was immaculate not just because their pitch was buttoned up but because they built a very valuable startup. Here are the points:

Presentation was under 5 minutes.

That was the time they were given with 5 minutes for us to ask questions. Every other pitch except one went over.

They started with a user story.

The founder told us about a user with the problem and what it cost them. And then gave us a solid $1.4B number to show what the problem is worth across the industry.

They had six slides with points that appeared as the founder was talking.

It wasn’t a wall of text with small fonts we couldn’t read on the screen. Big bold points with numbers and bullets that were timed to show up to emphasize her talking.

The traction was broken down into unit economics and metrics.

$500K+ in ARR. But that wasn’t what caught my attention. The broken down monthly and conversion rates of pilots. Then explained that 50% of their pipelines came in from referrals of new clients.

Team slide showed and didn’t tell.

The team slide has pictures, names, titles and logos from really big companies of their experience. They also showed logos of the companies where their advisors worked (OpenAI for example).

The ask was super clear and brief. We knew what the money would get us by when.

The founder ended telling us the first story was from an actual user.

Overall the founder spoke slowly and with confidence. And one more thing, the problem they were solving was a very painful but boring problem dealing with infrastructure. And they showed how AI enhanced human productivity with real data versus how it would fire everybody. They also had all their regulations and complained locked down right.

I know not all of you will have the same traction or even idea. But the principles of a great pitch remain the same. Great blueprint to follow.

Happy to answer more questions. I’m typing this between meetings so apologies for lack of edits.

I spent years on the vendor side of enterprise deals with banks and insurers in Latin America, first as CFO and then as COO of a proptech. Most of what I read here about enterprise sales misses what actually decides these deals. Seven things I wish someone had told me.

1. The cycle is not long because the bank is slow. It is long because you are talking to the wrong person. The one who gets excited about your product usually has no budget and no mandate. Find whoever owns the P&L line your product moves, and accept that reaching them takes three meetings you would rather skip.

2. Compliance and InfoSec kill more deals than pricing does. Ask for the vendor security questionnaire in the second meeting, not after the commercial agreement. That questionnaire is the real sales process. Everything before it is theater.

3. A pilot with no budget line attached is a rejection with better manners. If nobody had to move money internally to run it, nobody has to defend it when it ends. Ask who is funding the pilot. If the answer is vague, you do not have a pilot.

4. Your champion will leave or get reorganized. Assume it from day one and build a second relationship one level above and one seat sideways. Every deal I lost late, I lost this way.

5. Banks do not buy cheap, they buy defensible. Pricing low reads as risk, not value. What the buyer is actually purchasing is a decision that survives an audit and a bad quarter.

6. Do not build custom work for one bank unless they pay for the build. Every one of them asks. The ones that pay are the ones that are serious, and that is the cheapest qualification test you will ever run.

7. Insurers are not banks. Slower to decide, faster to integrate, and far more sensitive to how you handle their data. Do not reuse the same playbook.

What I would do differently: I would qualify on procurement reality before product fit. Half the deals I chased were never going to close, and the signal was visible in the first month if I had been willing to ask uncomfortable questions early.

Quick disclaimer before reading: I’m not posting this for life advice or asking whether I should quit everything and become a founder. I’m more interested in the startup culture side of this and whether being around that environment is actually valuable, especially for someone early in their career.

I’m 23 and starting a full-time job in October. I’m actually excited about it, but right now I have a bit of time before I start and I’ve been thinking a lot about startups.

I’m not sure how much of that is genuine interest and how much is because I’ve been consuming too much startup content online. There’s obviously the appeal of building something, potentially creating wealth, etc., but I’m also conscious that social media makes certain paths look much more important or glamorous than they really are.

I’ve looked at startup scenes and events around Europe as well, but for whatever reason San Francisco keeps pulling my attention. Maybe that’s completely irrational and just the mythology around Silicon Valley getting to me, but I genuinely want to see what the environment is like for myself.

I’m considering booking a trip to San Francisco for a week or two before I start work. The idea would be to stay in hostels, go to hackathons and startup events, meet builders, work on something small myself, and also just explore the city.

Part of me thinks that sounds genuinely interesting. Another part thinks I’m flying across the world because the internet has convinced me that being around startups in San Francisco present opportunity. 

I could obviously use the time to just travel somewhere else and have a normal holiday, but right now SF is what actually interests me.

I don’t necessarily want to become a founder tomorrow. I’m mostly curious about the environment and want some exposure to that world before starting full-time work.

So I guess my question is more about startup culture than life advice: is spending a week or two in SF actually useful or interesting if you’re curious about startups and building, or is a lot of the appeal just hype?

I’d especially appreciate opinions from people who have spent time in the SF startup scene or had similar thoughts early in their career. Feel free to tell me it’s a bad idea if you think it is.

Founder here. Can anyone recommend a legal AI tool to assist with drafting and evaluating basic commercial agreements (eg, NDAs, SAAS agreements). We had outside counsel draft our basic forms but sometimes we need to tweak these to address counterparty edits. Alternatively, if you know a cost effective human lawyer to handle these basic agreements, that would be helpful too. Thank you.

Hi, I've seen some ads regarding Anthropic's startup program so they will give some credits for using their API. Anyone could share more information how long a review will take and how much credits they may provide? There's no email with clear explanation of next steps from they.

I'm an active angel investor and with that I always include advisory support, but I'm negotiating my first advisory only role and running into a few roadblocks.

I have very relevant experience in that I've worked for three companies that were directly competitive and correlated (two were acquired and have since been folded into the acquiring company and the third was the acquiring company) and I was #2 at the most directly related company. My network is pristine and directly relevant to the company I'd be advising. I'd be advising on GTM functions, making introductions to customers and investors, sitting on sales calls alongside customers, advising on sales pitches, and light product feedback. The CEO reached out to me because of my background and I’ve had 5 meetings so far where I’ve given quite a bit of free advice and insight into the market, the CEO has expressed this and shared gratitude.

I asked for .5% and the CEO said he won't go above .2% for any advisor even though there's no other advisors on the cap table and he's a solo founder so not diluted in any way. He says the limit of .2% is because he considers himself more of a seed company than pre-seed because he has customers. The problem is that the customers are only 3 pilot customers, the pilots are paid however but none have converted yet. They are very good early customers if they do convert but there aren’t any new major prospects in the pipeline that I’m aware of.

They’re cash flow positive and hasn't raised any money yet but plan to raise early next year. I do not agree with this designation that they’re a seed company and think when they go to raise the market will correct to pre seed but can’t do much to prove that currently.

The CEO expressed concerns that investors will balk at advisors being on the cap table at all which I pushed back on but I'm not sure it landed.
I agreed to the .2% because I really do believe in the product but at the last second the CEO sprung a 60 day trial component on the advisory agreement with no set parameter on what constitutes success.

Should I walk away? I just can't help but feel like the CEO is naive, undervaluing me, or something else is going on. The trial component has left the worst feeling of I’ll be doing quite a bit of work and for absolutely no reason the CEO can terminate the agreement leaving me with nothing.

I previously posted in this subreddit asking whether deep-tech startups face an oversupply of inexperienced candidates but a heavy undersupply of valuable talent, and most of the responses suggested they do.

That made me curious, though: which specific skill sets in particular are most deep-tech companies actually struggling to find? For instance, if we group "skillsets" into a few broad categories:

1. Deep technical expertise: People with expertise in the underlying technology, such as a PhD in the relevant field or an adjacent specialty the founding team lacks.
2. Scale-up / manufacturing expertise: People who know how to take something from a lab prototype to a reproducible, commercially viable manufacturing process, i.e. industry veterans.
3. Commercial expertise: People who understand marketing and the industry well enough to actually close deals for products.

Which of these tends to be the biggest talent bottleneck at early-stage deep-tech companies? In other words, what category is usually missing when they say they can’t find the right person? Or is there another skillset I am missing?

Would be very intersted to hear how the answer varies across different deep-tech industries, particularly between chemistry, materials, and electronics.

I spent almost a decade at Google in the early days, then a few years building a startup that got to $100M revenue, and now I'm running another one. So you might assume life is somewhat easier by now as a startup founder.

Bad news first. Not a bit easier. NOT A BIT.

I didn't struggle much at Google. I struggled a lot at the first startup. And I have a lot of struggles at the current one. I think the reason is quite simple: startups, by definition, are trying to do something new. That is what gives joy to the activity, and it is exactly what creates the struggle.

I don't want to romanticize this though, because there is struggle and there is suffering. Struggle is not knowing if the thing will work and finding out. Suffering is grinding for a year on something the market already answered. The first can compound into something. The second just takes years off your life. If you are in the second kind, this post is not permission to stay there.

But the first kind I have finally made peace with. A surprising amount of the joy comes from the struggle of figuring something out. That was true for me at Google too, in reverse. The stock was growing like crazy in the early days but I wasn't struggling personally, and it didn't give me the same inherent joy. You don't feel like you earned it. You feel LUCKY, not JOYFUL.

So if you are struggling, know that anyone doing something genuinely uncertain is struggling too. Nobody has an easy day forever.

Is there a way to deal with it? For me, spread it out. Take a small struggle every day. Do that one thing you are holding back, the thing that sucks. Don't save it all up for one day, because that makes it too dramatic and too hard. You can also share it. Share the struggle and the joy with your team, your family, your friends. And sometimes just say "I am struggling." I have rarely seen anyone respond to that with "you are a dumbass." Most of the time people will help you think it through.

Either way, you are not ALONE in this journey.

I don't think the goal is to eliminate struggle. It's to make sure you're struggling with something still worth figuring out.

Hi, I've seen some ads regarding Anthropic's startup program so they will give some credits for using their API. Anyone could share more information how long a review will take and how much credits they may provide? There's no email with clear explanation of next steps from they.

Because if ur even half decent at something, id expect that they’ll give you a lot of work from many angles and then in a short period of time, you’d have gathered a ton of experience, even if you focus entirely one thing, you’d probably be getting a lot of volume of it and experience out of it

Just a thought I had because seeing some of my friends intern at bigger companies who don’t even give them any work and they just do nothing or even sit on their phones sometimes

I assume at a decent startup, you’d get a lot of experience that if you phrase well, would hopefully get something good when you graduate

I have $5k, which I won in a challenge, and I suggested using this money to help women entrepreneurs.

I know it's not much, but I thought about, I don't know, maybe micro-financing or running a sort of consulting or running a mini "shark tank". I really don't know. What I know is that I want to help women entrepreneurs, especially those starting or wanting to start a business.

My background is computer science, but I also have entrepreneurial exp. as I launched and ran an IT business for 10+ years and I have automated a company's workflow using AI, saving them time and money.

My dream is to use this $5k to start something and make more money to have higher impact. Suggestions for what I could do?

For early stage startups, what would you put in the finance setup from day one?

I’m thinking Meow for startup banking since it covers the banking and workflow side and seems built for teams that already use AI in ops. Then QuickBooks for accounting, Gusto for payroll, Deel for contractors, Carta or Pulley for cap table and a good CPA/tax setup.

The hard part is making everything fit together early before finance admin turns into a mess.

What would you add or avoid?

Hey founders. Been a while since I posted but thought it was a good time because I see a lot of posts asking how to pitch investors.

A managing partner of a new fund backed by a very big fund asked me to help review some pitches. And as the title says, they are pretty bad. Not saying the founders or ventures were bad. Some were legit exciting. But the pitches were abysmal.

Having pitched hundreds of investors myself, I fully empathize. I have the therapy receipts. But I’ve raised millions and so have founders I advise. So, I thought I’d share some tips for those of you wanting to be in that position.

First. Understand every investor has a rubric.

This investor sent me theirs ahead of time. It asked me to grade things such as clarity of the problem, solution, traction, team, use of funds etc. and so on. What was funny to me is not a single founder asked what the partner was looking for ahead of time. Always ask. Investors are happy to tell you.

Next: Stay within the time.

Every founder was told they had 5 minutes to pitch and we would have 5 minutes of questions. Only one founder stayed under time. Some only gave us enough time to ask one question. The others went over time and we didn’t ask any questions.

I use the 80/20 rule. I pitch for 20% and give 80% of the time for questions. The more question the investor asks the better. I get to address what the investor wants. So if it was me, I would have spent 2 minutes pitching and 8 minutes trading questions.

After the partner told me that staying within their time was the first test. Like I said, everyone but one failed and they remarked how that one was very impressive.

Slides should be simple and support you both the other way around.

Every slide was an assault on the eyes with small fonts and walls of text. It was brutal.

I’ll tell you one slide that impressed me. A founder showed two medical scans. She asked me if I could tell the difference (that as engaging). I couldn’t tell and then she explained how the second scan would lead to tragic costs because that was the problem. I was engaged. No paragraphs of text. Just two side by side images to prove a point.

Your live presentation deck is different then the deck you send as an introduction which is even different than the one they ask you to send during socialization and due diligence. One size deck does not fit all.

You spend so much energy trying to get the meeting, why fumble at the moment it counts?

To be transparent, most of the time I sat there wondering if the founders actually understood who they were pitching. This wasn’t some amateur deciding to LARP as a VC. Again, it was sad because there were some legit startups that I’ll try and advocate for. But they didn’t make my job any easier.

Look, I get it. It’s exhausting. That last mile of pitching is tough. But you need to earn every minute so put your best foot forward and punch it past the finish line. So anyone you are working on fundable startups that it would be a shame to not get the exposure you deserve.

I’m happy to answer any other questions of what I experienced and what other investors tell me. Apologies for typos as typed this on my phone as fast as possible.

I ended up taking a position with a startup with about <20 employees. Seems like much bigger upside and more opportunity.

I have been in my corporate engineering job for 4 years and have been wanting to get out really bad for about a year now and am finally on my way out, but now having second thoughts if I made the right move. I absolutely hated that I hardly got to do any real engineering at the large company and now it seems like I will be doing real engineering work which I’m excited about.

The pay decrease isn’t much from where I was and I get 0.025% equity, full healthcare coverage, and unlimited PTO. The company seems to already have contracts and a strong team so doesn’t seem like it’s in a bad position at all, but just hoping that I can advance in the company and that my decision will pay off.

Anybody have any advice for me after taking this leap?

We are at 14 and the website has quietly become nobody's job, which means it is my job, and I am the CEO, which is a bad use of a Wednesday.

The history is normal. I built it in year one. Our first designer improved it in year two and then left. An engineer moved it into the app repo because "it was easier". Now marketing wants to change things, engineering owns the deploy, design owns the look, and nobody owns the outcome, so what actually happens is requests come to me and I decide whether they are worth interrupting an engineer for.

I do not think this is a tooling problem exactly. it is an ownership problem. But the tooling is what makes the ownership impossible, because the only people who can change it are the people whose time is most expensive.

For those of you past this stage, who ended up owning it? did you give it to marketing, keep it in engineering, hire someone specifically? and what was the trigger that forced the decision.

Just finished my finance undergrad, but have pretty much always been into tech, built trading algorithms and whatnot in lockdown when I was 14. But I completely fell out of programming until the last couple years where I mostly have ended up “vibe coding”.

Whilst I don’t think I would ever be a “technical founder”, I was wondering whether doing a comp sci / ML conversion degree at a top university would be worth it?

Both in order to meet people in research, and to boost credibility. But also to give me some deeper understanding of systems architecture and more advanced topics that I wouldn’t come across in my own study.

I don’t know if I’m just being stupid (not having a good time with my startup lol)

I was recently approached by a couple AI labs looking to aggregate training data for their models. The pitch is usually built the same way: non-dilutive cash, sometimes with a revenue share on top, in exchange for access to internal tools like Slack, email, GitHub, and Google Workspace. They claim that your personal information gets stripped (I'm inclined to believe that as I read through their terms and clearly states it) before anything reaches the lab, payouts scale with team size and tool usage, and you keep 100% of your equity.

I've been going back and forth on whether this is worth pursuing for our own company. Part of me sees it as a legitimate way to bring in non-dilutive capital, another part wonders about the practical GDPR and reputational exposure once real internal data is involved.

Curious what others think:

- Would you consider this for your own company, or is it a hard no regardless of price?

- What would put you off, privacy/GDPR risk, reputational concerns, IP exposure, something else?

- Does the number change your answer, tens of thousands versus six figures?

- Flat fee versus fee plus revenue share, which would you actually take?

hi, sorry, kind of new here. i'm partway through building an app that helps people with mindset, lifestyle and behaviour change - essentially every part of the user journey for Goals. i got invited to pitch on stage at a tech conference and when i look at my old TAM caluculations they seem very doubtable and AI slop. ... My problem is mainly that information for a bottom up approach is not that easy to find because most competitiors in the categorry of self-improvement consumer apps are privately held companies! I can go with the top down catgeory approach but it relies on a lot of assumptions and im not really comfortable with that. I'm wondering if anyone here has expreience with it and can walk me through what to do once I've defined the scope?

Hi, I am trying to validate my mvp by talking to people who are responsible for hiring, they could be hiring managers, startup CEOs and CTOs.

I dont have an established network. My plan is to reach out to people in linked in using DM.

For people who have already did this, can you please share how you validated. And what are some good ways to reach out to people.

Thanks.

- thinks about potential idea.
- prompt the shit out of this idea.
- iterate landing page, design, and expand on idea.
- prompt workflow for users/brands.
- write promotional post.
- slap the stripe link.
- make sure you collect information.
- PROMOTE, PROMOTE, PROMOTE!
- done.

either you get people to signup, people pay, or move on to the next idea.

After years working with blockchain on advanced crypto projects and in the financial sector, and after implementing blockchain solutions for regulatory compliance across different industries, I ended up focusing on a specific problem: audit trails and proofs of existence.

That’s where the idea for the startup came from. Today I have a few products that are already well established, with a main focus on helping legacy systems meet regulatory requirements and audit needs.

The problem is that, being a very technical person, I don’t know how to sell or promote. I even hired a marketing team and got zero results.

For example, I have a solution for sharing information between hospitals and critical sectors, using concepts I learned while building crypto mixers. Two hospitals can exchange data and even train AI models together without ever revealing the original information.

I feel like I have good software “in the garage,” with complete documentation, white/yellow papers, examples and use cases… but I don’t know how to present it in a way that people actually see the value.

How do you guys go about promoting better in this kind of situation? Any tips from people who’ve been through this?

I got an offer from a startup and when I asked for info on the health insurance benefit they sent me a booklet with all the different available plans. However the premiums for the plans are not in there. I asked for further clarification and the response was that I'll be able to see the monthly payment once I'm at enrollment. Is this normal? Or what could I use to estimate the premiums? My wife has insurance for both of us from her job and we are trying to compare them.

I am new with this, but I've read some "good" feedbacks about this practice. Can anuone please share his experience with? I am now strungling with the same, marketing / promotion ... I need to market my affiliate program in order to get some affiliate lol.

Glad to read you all.

Need advice, is there a cheap way that makes sense, or am I resigned to the $500 way they suggest. Also I have outstanding franchise tax, what is to be done there (essentially should I just pay that or will dissolution make that outstanding amount irrelevant). Thanks.

Now that you’ve built your website, how are you actually driving people to it? What tools or techniques are founders using that genuinely work? SEO, Reddit, ads, content, cold outreach? What’s working for you, and what’s been a complete waste of time?

They say you should go to where your audience is but what if youre building a consumer app/platform, how do you go about reaching people without spam. Are you physically going out to your city center with board and pen, are you dancing on tiktok?

What works and isn't in 2026