What would be some appropriate questions to ask a successful business owner for financial advice?

Most people are lazy. They won't do anything other than daydream about becoming your competition. Next point: if the barrier to entry to your marketplace is low, then it's all about selling. Rather than focusing on features or what you do ("We make websites"; who cares?), start talking about serious problems your solution fixes for your customers. Things like: > reduced waste/rework > minimized project times > lowered interpersonal struggles > shrunk sales cycle > sped-up time to profitability on new products. When you concentrate on these ideas, you differentiate yourself and move out of being a commodity provider.

I love this question! Thank you for asking it. If you don't mind, once you finish I would love to know more about your startups and what led you ask this question. No judging, but everything is a learning opportunity - I guess, hence we're both here. My name is Humberto, although I now run a hybrid global marketing agency, I started drawing and selling my designs to shirt companies in FL a long time ago, traded medical sketches for medical treatments LOL. Over time my passion for art led me to pursue a full time career making a living with my art but that didn't pan out. Through that time though I was learning how to sell, learning technology and programming basics. It was this that got me involved with the startup community in Phoenix, AZ area to what is now globally known as #yesPHX. My creative side was the driving force behind all the Startup Weekends, Pitches, pursuing ideas, joining teams and seeking investors to pitch shamelessly to as well as building relationships and strategy. I learned a lot. Including the fact that it was my creative side that drives me and my passions. That "Entrepreneurial ADD" as I like to call it was reduced when I was working on something that allowed me to be primarily creative rather than doing managerial or repetitive stuff such as pitching and driving sales or improving code. It took 2 startups with financial backing to realize that I didn't want to grow a business for myself, I enjoyed the creative challenges of figuring out how to get them growing and grow them and then move on - not being stuck running them. I found out I was a wannapreneur. But this was an opportunity because knowing that I didn't want to be stuck growing a startup for the sake of money or nerdy fame helped me realize that I wasn't going to 'change the world and make it a better place' I would be like most of us just stuffing the world with one more app or service that we can probably go without or be a feature of an existing rather than a new company. Anyway, through this time I was consulting with other startups on growth, creative ways to grow (now commonly coined as Growth Hacking by S. Ellis) this led me to make a living consulting, I was a young 20' something hispanic entrepreneur helping business men and women of all ages and industries because of my experiences. I came in and evaluated their situation, found holes, provided ideas and solutions. I would help execute then I would move on to another challenge elsewhere. A wannapreneur I think is a bad term for a certain type of personality such as what I can relate to. I want to work, I am creative, and I am trying to make the world a better place but I don't like being stuck forcing growth of my own company. This has allowed me to grow my company by focusing on driving good growth for my clients and being helpful which generates referrals. Depending on your experience you can try a similar path in pivoting your skillsets to something else. That's what pivoting does for the most part " what resources and experiences I have and what other ways can I utilize them better?" What relationships did you build? can you leverage those as opportunities for others? Try joining a startup as a sales agent, customer service, or get yourself into a franchise which have to provide structure and help.

I have not heard of the $1,000 rule; however, the determination for the need of a business license will come more from the requirements of your local government. Check with your local economic development office to determine what licensing would or would not be needed for the particular type of business you have in mind. Another factor would be the type of legal structure you intend to operate under (e.g. Sole Proprietor, LLC, Corporation). The corporation and LLC would have to be registered, while the sole proprietor may not have to. Schedule a call to discuss your options in greater detail.

SOM refers to the portion of the market that your business COULD actually capture, as you stated: "[the] % [you] can realistically achieve from the SAM." Let's use an analogy to break this down - and pretend you are talking about fishing instead of project management software. TAM refers to all the fish (that manage projects) in the sea. SAM are all the fish (that manage projects) within casting range of the dock you fish from (ie your solution is viable for them). SOM are the number of fish (that manage projects) you can reasonably catch within the amounts of time, energy, and bait you can allocate to fishing. The question within a question you ask about guidelines on believability is a great one. And, while I don't have a guideline or benchmark to share, I can confirm your instinct; ensuring that your projected SOM is reasonable is absolutely critical. The best way to project this is by having at least some of the equation variables grounded in reality - ie, actually catching some fish. If you can show how much it costs to acquire a customer, how much it costs to service that customer, and how much you'll make from that customer over a lifetime, you've got some great empirical evidence to show how you'll achieve growth within your SOM. I don't think of SOM as a target - it is rather the theoretical maximum number of customers or revenue I can achieve within the (sub)universe where my product or service adds value. In the end - the number is important - but not as important as how you present it, and how you'll approach it with your product. As an investor, you want to see more than just the answer - you want the thought process behind the answer. Was the founder thoughtful in their approach, did they look beyond the obvious while remaining pragmatic? Do they understand clearly why the SAM (macro-environment) and SOM (micro-environment) break out of the TAM in the proportions they've listed? More than happy to dive deeper on this.

Let others do the heavy work: use a software solution. There are many out there, so start with exactly what you need to know (the information you need to have available comes first, then you determine what and how to track). Do some research on the available software and then call up a few companies and explain what you need, asking how they solve that problem. Think of your priorities here: the right solution should be simple to manage, give quick access to information, not require a lot of interpretation, etc. Beyond the software, think about what you can plan for to help give you the information you need. Build certain budgets to help manage how you categorize and view different invoices and areas of cashflow. Remember, the key is to have immediate information, not just data.