Self-taught Technical Expert
CEO of Kanpeki (Software Services Company)
CEO of Warpcore.io (Software Development Tool Startup)
CEO of ZEROkW (Electrical Engineering Startup)
Startup Technical Advisor
Startup Business Advisor
Mobile applications
Self-taught Technical Expert
It's important to differentiate what is and isn't tech. For example, AirBnB is not tech. It uses a bit of technology, very basic and simple, to support a business. Likewise, most mobile apps are so simple they can hardly be called technical. However, there are also startups which do require serious tech knowledge (which you can either have or get from me / another tech advisor), like ebay, paypal, amazon, rackspace, ... companies which require an important investment in technology to exist. In your case, I would say take some time to figure out what you need, try some quick prototyping with a good web developer, using android:chrome on a mobile phone and when you're 100% positive that's the app you want, get a beautiful skin from a professional designer and ask for it to be made in native code, publish and see how it fares.
Startups
Self-taught Technical Expert
I hear of a chef who is pretty much product manager and spokesperson as well as another person who is brand manager. Who's the CEO ?
HubSpot
Self-taught Technical Expert
I think you might be adding fat more than you're trimming. You're talking about moving away from one platform into another platform, plus WordPress, plus integration, plus migration costs, plus training, plus any issues infusionsoft might have minus any issues hubspot has. Now maybe that's worth it for the design flexibility, but clearly you're adding fat and costs and that means there must be a corresponding increase in returns. tl;dr: don't underestimate transition costs.
Funding
Self-taught Technical Expert
You might want to look into convertible notes, I hear they're rather fair and help you dodge that issue until the next round of funding. They're also pretty much standard for seed funding in SV from what I've read. I think the whole "skip the valuation" part is a major improvement, so the Business Angels (or your family) only have to answer one question: does this business have a good shot at succeeding ?
Mentoring
Self-taught Technical Expert
I was born a maker, and I've been an Entrepreneur for six years now (and a wannabe for much longer before that) and I think the worst advice I've got was from people who had never taken a step of the journey. People with academic (or other) credentials who advise you based on theory and completely miss the point of entrepreneurship. They know about the theory of sales funnels and marketing strategies and much more but they've never made a cold call. Or a sale for that matter. The best advice I received was from my godfather, who is an entrepreneur and salesman. That advice was simple, brutal and actionable: "If you can't sell it to a customer, how do you expect to sell it to a salesman ?". That made me realize that you don't stand a chance at success if you can't convince anyone. A good startup advisor understands all of the field he's advising about and knows what a startup is. He knows how to apply his knowledge to the constraints a startup faces and how to deliver that wisdom in regular words to support the startup's decision process.
Software Development
Self-taught Technical Expert
I don't know about the others but I'm in Belgium. Generally speaking, you really want to focus on two things: 1. Where to fish: on average, where is the best developer for a given price ? Generally where high quality education and low demand job market meet. Western Europe is perfect for this as it has some of the world's top schools while paying developers next to nothing (about half of what they cost in the US). Some countries in Asia come to mind as well although the cultural lack of creativity may be an issue. Don't be lured by the low cost countries, I've yet to see software developed in Eastern Europe or India that is better value for money than what is produced in the US or Western Europe. 2. What to catch: how can you tell whether they are the best software developers ? It pretty much takes one to know one. Assuming you have a business mind you're pretty much lost without a tech advisor because you'll always pick the guy that makes the most sense to you without really knowing whether he's right or wrong. Which is what I do too, with the major difference that I know how their mindset is going to affect practical outcomes. Then come the practical questions: 1. So how do I pick a Tech Advisor ? The short answer is pick me because I'm the best. The long answer is that you need to find a way to filter profiles that match your needs. I could help you with that if you give me a call. 2. Any code, any language: this does not make sense: you will not find the best developers willingly using a technology that is not the best tool for any job. This is one of the easiest way to filter out bad candidates: ask them what technology they would use if they were given the choice and why. This also gives you the awesome opportunity to assess their self-improvement dynamics: do they have a good answer, are they willing to change their mind for a better one, etc.
Startups
Self-taught Technical Expert
If you haven't already, you might want to look into external help for your strained relationship with your CEO (yes, just like marriage counselling). Relationship experts can really improve the quality of the communication and help resolve existing issues. I don't know what your personal goals are, but you could probably try becoming CTO at another company between 2x and 5x the size of your startup.
Growth Hacking
Self-taught Technical Expert
I believe the main reason Uber and AirBnB both grew extremely fast is that they adopted a new (is it really though ?) approach to startups: fake legality until you make it legal. The idea is to pick an illegal activity in a somewhat grey area and to start making money without bothering about legal until you're big enough to lobby your way out of it, either by way of "job creation", PR or just money. The main reason most people did not try to build Uber or AirBnB before is because they stopped at the analysis step with the conclusion that it would be illegal, against regulations and thus an unwinnable battle. Uber delivers an awesome affordable service by a) offering a taxi service, b) circumventing all taxi laws, regulations, ecosystem and related costs and c) enabling their drivers to not declare their revenue. By cutting a few middle men, spending $0 on regulatory compliance and having a few "a little money on the side" drivers, you end up with better prices, happier drivers and none of the sluggishness of bureaucratic processes that prevents simple reviews from ruining a driver's career instantly. At this point in time, a lot of the services offered through Uber are at least partially illegal.
Start-ups
Self-taught Technical Expert
You want a Technical Advisor first, and a CTO second. The rest is really none of your business as a CEO. In my opinion, you find a capable CTO, make him responsible of product development and leave it at that. In many cases where technology is shallow you might not even need a CTO. But hiring people before you have a Tech Advisor, who can answer your question in detail with understanding of your specifics, is likely going to create problems. Last but not least, I believe the recipe in the first answer is far off the mark: two full stack engineers, one UX and one front end is way too much for most startups - if not all -, you'd be bleeding equity or money for no good reason.
Start-ups
Self-taught Technical Expert
That is perfectly normal and really just fine. Creating a company, growing a company and maintaining a company are three different jobs and the best fit is rarely the same person. Now that your creation has matured, it may be time for you to hand it over to someone else who will protect your investment while you find new areas of personal growth, such as another startup for example. You probably need to find yourself an operational successor you'll be happy with, gradually hand over your responsibilities until your level of involvement matches your interest - in your case that would probably be board member / adviser only - and enjoy being a shareholder of a valuable company.
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