This is an interesting thread of responses.

It really comes down to who cares more. For people who I need because they are the right price, the right experience or the only option I do whatever it takes to keep them happy.

I can’t even get someone to come out for an estimate for less than $100.

You’d have better luck if you shared your strengths and weaknesses. Your post is the equivalent of a romantic asking someone where to find a spouse, with no context to what you’re bringing to the table.

Example, you could be a 12 year old with big dreams or a successful business owner with significant capital. Since it’s unclear, people are more likely to not bother - when you provide details that don’t make people guess at what you’re bringing, you tend to better find the people you’re looking for.

People don’t like dealing with their own problems, your path is a reminder to them they are losing.

It helps if you look at it as their problem, not yours. It’s not about you, it’s about themselves.

Now that said, I do wish I had helped my brother out more when I did have the opportunity… now that’s he’s gone I should have known how much he was struggling.

The answer to your question is you can’t do exactly what you want to do but it would be nice wouldn’t it?

Some larger brands show up as Facebook Interests and I’ve been able to target that way from time to time. For example, fans of Tony Robbins are accessible and at one point I was able to find fans of Grant Cardone… but everyday businesses aren’t big enough to get their own audience for interest targeting.

The demographic data of a company, it’s pages etc belongs to the company itself. Platforms like Facebook don’t expose it to the general public.

I’ve been in startups consistently for almost 30 years now. Sounds like a typical success path except one thing - attitude is everything. Reality is what you make it, enthusiasm goes a long way… find the success in all of these failures and turn it into the most positive experience. Focus on that and you’re going to be fine.

You’ll have to trust me when I say I have a lot worse ‘damage’ I’ve dealt with and have always been able to turn things into a positive.

Most startup advice isn’t even the best advice for startups - the unicorn founders give terrible advice

I know someone who ‘heals your dna trauma’ (trauma passed down through generations) and does orgy retreats to discover your sexual being.

If I was going to put $300k anywhere the last place I’d put it is a company with high failure rate and low scalability potential.

Yes, I agree - the take away is that the document has value, hopefully tremendous value in understanding where they stand. Most CEOs not being technical need someone they can trust to provide a true assessment and give them an ‘unbiased’ report on the state of their business. Especially the fast growth startups where everything seems to be falling apart and they just can’t seem to get a real solution. Often times I’ll report the staff is shorthanded for what’s necessary to maintain a business at their pace… I try to do my best to stay on the good side of the existing teams and not crap on them directly. Being in tech for over 25 years and getting shit on by outside parties is too common from people trying to make a quick buck. I like to think I bring an ethical approach to doing what’s best for the business.

Also - getting access to their actual order system helps me fully understand the risk / opportunity of the situation.

I think you meant to reply to my comment - From your questions I’d say you’re looking at this from a job perspective, I’m looking at it as a relationship.

The difference is I’m not trying to sell long term deals out of the gate - I never want a situation that gets stale over time, it starts to feel like employment situation… as hired expert you’re the boss, as an employee it’s not as effective.

You can stay as long as needed, calibrated to what the company actually needs. Every company is going to have different problems, budgets, size - a small company with simple problems don’t need me forever and I don’t need them.

The audit process helps you identify the opportunity unique to the company you’re working with - what you do from there should reveal itself as you go.

You either have package options or custom tailor it around the opportunity.

I recommend trying to avoid hourly rates.

My best strategy is to sell an audit / discovery package first. I have about 12 sections on a report I do and give each a proprietary/opinionated score based on my findings. I also have a second factor I call risk, which helps set my opinion on priority. A few of my categories are documentation, team, security posture, data model, disaster recovery, scalability, code review(s).

I usually write a page or two for each section based on my process.

They give me free reign to come in and poke around, access to the resources (people) I need to accomplish my research. It’s empowering to get into everything, under the hood and point out all their problems.

I provide an example audit report and sell it based on the customer, but usually 10-20k for about 2 weeks worth of work with a 30 day delivery window. I’ve also waived the fee when I felt I could work in a $100k+ deal for it. Even if they want me to fix a specific thing I always start with an audit, it just immediately puts you in a position of strength and the knowledge you’ll have once you go through it will make you invaluable to the company. It’s also very easy to sell, you ultimately eliminate the complexity of trying to negotiate solving a specific problem - which you can’t do blind and need to dive in anyway to make an intelligent decision. Without a package, the research can become implied as free as part of a scoping estimate. You also only have to sell two things - your expertise and their trust.

This allows me to get a package project with a fixed timeline out of the way as soon as possible and not waste time… it also serves the purpose of providing a deep dive into all aspects of the business and can identify opportunities for work.

The secret with tech audits is you will ALWAYS find something that needs addressed, and you’re the person who found it, documented it and hopefully knows how to fix it. As a true CTO, you may not even need to fix it yourself hands on, just know how to find the best options to get it fixed.

Giving away 45% of the company for a first investment isn’t a strength, it’s a weakness. If anything he should get less.

But it’s really worse than that, having less stake than your investors is already a foolish mistake and you haven’t even started.

You will either be smart and run or regret it once you realize you’re blinded by greed and/or wishful thinking.