This sounds like a solid road map. Do you mind giving some insight as to how you learned VBA/Excel enough to consult and where you found your consulting/contractor gigs?
As someone who turned 30 recently and would classify my 20's as 50/50 win-lose, I feel I can add to this.
I am single, however family is becoming increasingly important, but to each his own. As much as I dreamed of being a playboy entrepreneur in my 20's, I started tuning in to what I really want, and it's scary.
How will I still achieve my dreams and embark on something as demanding as a family? Feast or Famine is not an option amongst other things, but this is not about relationships, it's about career.
My recent job search was eye opening, I decided to get back into the working world after 8+ years and here is what I have boiled it down to:
1. My biggest mistake while I was an entrepreneur was failing to develop a role for myself. Although you may have to wear many hats in your day to day, you should always try to become an expert at what you're good at. For example, I did marketing and development, pretty good at both, but when looking for work I did not have much of a portfolio and to be very honest, I felt like a hack. Stay prepared and be able to demonstrate and prove your ability at any given time.
2. Failure happens. The delicate part is not looking desperate. Lifestyle change, sparked interest in a new industry or just simply making the next step in your career are all good reasons for transitioning from founder to employee. However, I felt there was some judgement passed on a few occasions. Forget them, it's not worth it.
3. Going out and taking a swing at your dreams deserves a lot of respect. There is so much mediocre in this world that an attempt to do something substantial in your life is not crazy.
4. Being a founder is a thankless job. There is no love until you become successful, or at least look like it. Forget what society thinks, you will almost never get the response you want when you make this decision.
5. Optimize, automate or delegate. After years of overworking, deferring life, missed encounters..... It's not worth it. Having a family may make you a better founder because it gives you boundaries. Respect your time, set your hours and give it your all when you are working at it. Nothing is perfect, but it's amazing what you can achieve when you have 8 hours to GTD.
Spent 8+ years doing web dev, marketing and biz dev for local companies in NYC. Have worked as a marketing consultant in an early stage startup that eventually went public. Primarily focused on growing companies and generating revenue in a lead role. I built many businesses from zero to over $200k/mo in revenue in NYC, including building web presence, developing and executing marketing plans and expanding services and service areas.
Very motivated to move into a full time position for a startup. I'm single, have no commitments, mature and focused.
Reason for move: To pivot away from local into a new industry.
However, I am ready to go above and beyond at any position I am at for my own personal reasons, so it won't be much of a stretch, just a taste of what's to come.
The relationship between technical and sales is always going to be complex.
A salesperson has to not only sell, but retain customers. It's their job, regardless of where the product is at. Customers are not easily acquired and the position is unforgiving.
As a hybrid sales/development guy, I was always conflicted selling products that I found myself having to convince users to stick with it on the renewal, because the product is not performing as it should or as promised. It was the technical side of me knowing this product is not really where it should be, just good enough.
And the clauses, yuck!, cancellation fees to end contracts, worst conversation to have with someone you're trying to build a relationship with. For anyone with a conscience, it's a hard position to be in but that's what you are being paid to do, sell. To survive you have to be at peace with the process and have a long term outlook that the product will get better.
It's crushing to have to sell a not so great product just as much as it is hard to push one out. I think what really makes the difference is the company culture and shared vision. If people are not ultimately working toward the same long term goal, there is going to be a disconnect.
Thank you for the advice. This is all very new to me.
You mentioned visualizing a dream role, this is a fascinating thought. Since I wore many hats over the years as an entrepreneur, if I were to create this dream role, could I market/suggest it to companies I am applying to?
Surely this would probably only work with smaller companies, of course, but do you think this is a possibility?
First, I want to thank you for the thoughtful reply. Just like many of you here on HN, I love the internet. It's my life and I've seen it evolve since I was 8. That feeling of never getting the opportunity to even interview for companies you're passionate about is hollowing. I'm glad to see that I am approaching this all wrong.
I really like this approach, I don't mind putting in the work to do some building for each company I choose to apply to. Will start this immediately.
1. Everything is negotiable, try to work it in your favor to not have to choose. If your going to lead a company, negotiation is a good skill to pick up.
2. I have always felt there is far too much anxiety around technology/startups ... will it be there when I arrive? Will I still be relevant? Urgency is great when you jump in, but rest assure it will be here when you come back, if you choose to take the time off.
3. Do you want to run from regret or follow your heart?
4. Put your degree as a priority unless you are absolutely passionate about what you are postponing it for. As a 30 year old drop-out, sure it's nice when you have money to walk around and look like a genius because your successful, but it brings on additional insecurity and uncertainty when you do not have that paper behind your name on the way up. How much time do you spend climbing vs. time spent at the peak? Prepare yourself for the climb.
5. Take the trip, discuss your flexibility, listen to the idea, take time to evaluate. When an idea connects with you, the question changes from "what should i do?" to "how do i make this happen?"
Lot's of great advice from the others also. Good luck none the less, you have two really exciting paths in front of you, so its already a win-win.
Fastest: Incorporate in Delaware, cost $157+$20 overnight Fedex for a C-Corp, 24 hour turnaround, registered agent Incorp which is free for the first year and $99 after, done by fax. 10M shares at .00001 par value. $350~ a year franchise tax. Some banks may require a Certified Copy but my bank did not, which is an additional $50. Merchant accounts are pretty easy, just need to apply for one either at the bank or use a service like Stripe mentioned in other posts. All merchant rates are negotiable on the most part. I can start a new business within 72 Hours with merchant account and bank account, incorporated, full startup documents.
Foreign Corporations depend on if you have employees physically located in that state, certain states may differ. Most startups don't follow this rule, it's the wild west in the beginning.
Just make sure you keep good records and you get a decent accountant to make sure you don't get surprised come tax season. If your looking at the lowest tax rates on corporations, I believe Singapore and Hong Kong are great STABLE options, however they come with their own issues when it comes to accepting payments and also are much more costly to set up.
Get your corporation in order, get a merchant account and start making money. These questions are best left for accountants and even at that, not everyone will give you the same advice. Once you have revenue and you have an idea of what your working with, you can see if it's worth incorporating in another state/country.
PS: If your a startup with founders, check out Clerky.com. Very nice guys and will get your corporation done properly. Worry-free. I didn't use them because I was looking at maximum cost savings by doing it myself, but will invest in them later if we need to redo the paperwork or just flat out start a new company.
Start looking, the worst thing I did in my 20's was doing the same thing over and over for years. Yes, you can learn on your own and grow - which is a must, but doing interesting things is absolutely important to keep your passion alive. At the same time, make sure that you are communicating your concerns with your manager/ceo and don't put yourself in the position where you become a volatile hire.
I was once told, a squeaking wheel always gets greased.
Usually startups that make money the fastest are ones with a revenue model, an understanding of who their customers are and a way to get in front of those customers.
This is a very broad statement, but I think if you can apply this checklist to your ideas you will be on your way.
Example:
Product: Website uptime monitoring with SMS alerts.
Revenue model: Free up to 1 site, $5/mo for 5 sites, $10 for 15 sites.
Target customers: Freelancers, Small web shops, owner operators.
Where they visit: Web Design Blogs, Freelance Blogs, Web Dev Podcasts, Tutorial Sites, Web Design Galleries
How to get in front of them: Banner and sidebar ad's, Reviews from related blogs, Press Release, Free Trials, Guest Blogging, Social media, cold calling, email blasts, podcast sponsorshop.
This is just a random idea I pulled out the air, but it could be executed immediately because it hits all three criteria on the checklist.
1. Start to develop a work/life balance. No one can tell you how many hours you should be working or what to do on your downtime. This is just the beginning - you CAN prevent burn out.
2. Start to network, find other entrepreneurs and listen to them. One day you will need someone to listen to you. Not all advice is actionable, but it's crucial to get multiple perspectives so you can play it out in your head. Eventually you will have enough plays in your head to tackle most, if not all problems.
3. Get your product or your voice out there. You need some validation of your ideas and thoughts. I tell you this because I wish I did this earlier.
4. Most of the best advice you will ever receive will be the regrets of others.
5. Capital is to an entrepreneur as a job is to an employee. Idea's are worthless if you cannot execute them. Cost to open a business is at an all time low. Low is not free.
6. Don't fail broke. Know when to cut your losses. I have learned that most people don't cut their losses because they are guilty that they have not done enough to give their business the best shot possible. On the flip side, if you are putting your all and you still 100% believe in your product, you need to get that passion and drive in front of investors to buy yourself as much time as possible. These have been the best times of my life, win or lose, never regretted a moment.
7. Don't ever stop yourself from doing whatever it takes to be successful. At my current startup, I am in the field everyday (I am building a marketplace), answering calls and doing physical work that is far below my pay grade. Why? Because at this point of the business I am far better off doing what I am doing now and to grow accordingly. Don't build an illusion of success by having office space, hiring people to do things that you can do yourself at first and creating the impression that things are happening. Let it come naturally.
8. Finally, Learn to build a life without regrets. There is are no hard and fast rules. You will regret shit, fix it immediately. Move on.
This sounds like a solid road map. Do you mind giving some insight as to how you learned VBA/Excel enough to consult and where you found your consulting/contractor gigs?
Thanks!