"Cap" is applicable only if you are raising via a convertible note. If you are doing an equity round (issuing new stock (called a primary, is most normal) or selling existing stock (called a secondary) then you wouldn't talk about a cap but a "valuation" instead (pre or post money). In that context a cap is short for a valuation cap, meaning the highest possible valuation that will be used to calculate the conversion of the note to stock during the next fundraise in which stock is issued. A note is like a promise to give you stock in the future in exchange for your money now.

"Flipping" companies is a very rare activity, Private Equity firms are among the very few specialists of that trade. Some stints in i-banking, PE, or Corp Dev would help, but so some P&L experience, especially in turnaround scenario. Short of having massive personal wealth, a leveraged buy out would be the only option and that raise the bar even more in terms of the type of performance needed to make it worthwhile.

Some states in the US allow for what's called a Series LLC, where multiple companies are under a single entity If you're the sole member of the LLC (Series or traditional) you may also be able to be a LLC for legal reason (liability protection) but a treated as a S-Corp for tax reason (more advantageous in many case)

TAM, SAM and SOM are nice terms to put on a powerpoint deck but ultimately they're not useful for you to run your company Your TAM is huge, that's great, but target a segment where you can make a difference and make that your SAM. Amazon started with books and then expanded, if you start with everything but you only have a handful of SKUs per category you'll get nowhere on revenue, have larger costs, and customer experience will be terrible. Uber started with black car (premium) service only before expanding, amazon books only, Tesla with just one model. So pick a segment to focus on, do a swag of your TAM, SAM etc... and focus on execution of the business rather than the pitch deck

anything >10% a YEAR would already be somewhat a concern for me (I do M&A of B2B SaaS companies) 10% a month is a big issue, either the product disappoints, the price is too high, or the engagement model isn't suited for SaaS and should be a one time purchase.

With all due respect, that isn't a good idea. If you do feel that you'd be better off bought by this competitor it's completely OK, but having customers be matchmakers is a big no-no. The message to both parties would be harmful to you. Customers would see this as a sign of potential abandonment of your product and therefore avoid buying it for fear of discontinued support. The acquirer-to-be would see this as an odd and unprofessional approach, either negatively affecting their potential desire to buy, or simply the valuation based on this showing of limited business acumen. You can reach out yourself or use an advisor (independent or investment bank, depending on deal size) Good luck, happy to help if needed

I think you may be using the word "leadership" with a different meaning. You seem like a go-getter and a potential high performer (do more, do it very well, do things beyond what's expected of you), but these are different than a leader (inspire other people, set direction and governance) or a manager (optimize resources use, human or otherwise) A low-risk, good way to grow and stretch your talent, comfort zone and how people perceive you is to take on special projects. Ideally special projects that will lead to new products and new roles down the line, that way if you perform there is a natural transition towards the new role. The reality though is that a company of 25 employees and a culture such as the one you describe may simply not be one where growth opportunities abound.

Templates can help a bit, but in reality some business models are best explained in their own ways, and business plans will contain the same headers but wildly different content from one industry to the next. Talk to people about your business, when you've found the simple and repeatable ways to explain what it is, why it's compelling to some people, and how it could grow and be profitable, you have the building blocks for the business plan.

There are plenty of ways to present yourself that won't seem desperate, such as saying that you feel that your original vision could be better realized as part of a larger organization (either because more resources or complementary offerings) or the perfectly acceptable "founder wants to move on to other things" Any buyer will be more interested in the potential post-close than in why you sell. Appease their fears about the quality of the business and the transition (retention of talent and management is often the #1 risk when buying a small business)