I don't know about you, but I'm finding it hard to believe we're nearing the end of August. I can see the light changing and scent of the air tilting towards fall. This week I focus on how a successful angel investor thinks as that applies to how you can approach your work. I also look at why you may want to be a niche player and some tools for managing your digital work life.

Prepared to win through losing

I'm no angel investor but I've learned a bit about the process. According to Jason Calacanis, you have to change your mindset when it comes to Angel investing. Our minds our not conditioned to handle an onslaught of bad news. We short circuit.

In angel investing, you have to be able to accept bad news in terms of failed investments over and over and over until you get to a win. You have to be okay with losing money. You're betting on the founders story. That their world changing business will do so.

In the world of angel investing, you have to be willing to lose a lot and keep going before you win. He also said that a good strategy is to wait until a product is in market and you hear how good it is from a customer. On top of that, the single biggest reason for failure is that the founder quits. Gets burnt out and doesn't keep going.

That's what keeps most of us from success too. The second biggest reason is a company runs out of money. I've heard others say that angel investing is not the best way to make money. You can do better building something on your own. For less money and less risk.

Whenever you hear about the success stories of companies like Uber, those are outliers. You don't hear about all of the failures. Uber delivered a 4000x return on initial investment. Which equates to $10,000 turning into $40 million.

That is not the norm.

Good is 200x to 300x return, which may be one out of ten. Or more. Jason credits some of his success to timing, starting in 2009 when the market was at the bottom. And being in Silicon Valley and having a solid network. Another factor Jason cited was that in 2009 there weren't very many entrepreneurs. You had to be incredibly resilient to build and launch in that market. It will be interesting to see what comes out of this current time.

As you think about what to do, consider what you try an experiment. Some succeed. Some don't. That doesn't mean you're a failure. It just means that first thing didn't work out. Or maybe the second or third. It's the same as in the start up world. Many don't succeed but the most enterprising founders land on another idea and build from there.

Both Twitter and Instagram started as completely different concepts. In Instagram's case, they noticed that what people liked most about their original product was the aspect of sharing photos. And so they pivoted and launched Instagram. Spend a few minutes listening to their story on How I Built This.

Looking at a very early stage start up as an experiment is how Jason approaches Angel Investing. It's only when a company gets to 10 to 20 employees and several million in revenue that it becomes a real investment.

The take away is that how you think dramatically impacts the solutions you develop. In whatever you decide to pursue, look at your mindset. Look at how you're approaching the problems. And how you are approaching the failure or success. No one, regardless of pedigree, is that good at picking the winning companies. That's why you want your retirement savings spread across many different funds or investments. And it's why it's ideal to have more than one revenue stream. Or try more than one idea if at first you don’t succeed.

What experiments are you working on right now?

Are you a Generalist or Specialist?

Speaking of experiments, what are the areas that interest you most? Those in which you can go an inch wide and a mile deep? Where you won't get tired of the time required to get critical mass before you give up. And that align with what others are interested in. Not sure what that is? Do some searches and find out what questions people are asking. Look at Reddit and Quora to see what questions people are asking and that may align with your expertise. If there is traffic, and even a little competition, that means there's a market. It need not be a huge market. Just enough. And that's where you can test different assumptions.

To get strategic about this, use a keyword tool to analyze searches for opportunity. The best are paid and I like Ahrefs which offers a 7 day free trial. Moz is a close second and offers a 30-day trial. They're not cheap but can save you some time. Try them for free to see how they compare to the free tools like Google’s Adwords Planner.

I always recommend the scrappy approach first.

Go with the free options until you exhaust what's possible. Only then will you know what’s worth paying for. Pay to save time. Go deeper. Outflank your competitors. For most of us, free works just find out of the gate.

Why appeal to a niche rather than something with broader appeal? Many of us may feel inclined to appeal to as many people as possible thinking we'll have more chance of success. But If you invent a product that is broad, then competitors can easily take over you. Particularly if you compete on price. And then it's a quick trip downward.

When you own a niche you'll have less competition and it's hard to be dislodged. Especially if you become the biggest fish in that niche.

The danger in a niche is that if the market suddenly dries up because of a technology shift or other evolution, it can be hard to pivot rapidly and you could face a quicker death. When you're general, it's easier to pivot and remain relevant as long as you can fend off the competition. Both have their merits. You have to choose what aligns with you. Remember the fax machine? It was invented in 1846 as the "Electric Printing Telegraph" by Alexander Bain. It adapted to different niche audiences until largely supplanted by modern technology.

In the job market, the generalist sees so much competition and it is hard to stand out. If you have a valuable speciality, it's much easier to stand out and command higher value. However, as a specialist who finds their skills are no longer needed, it's harder for to adapt. The generalist can transfer their skills across many different areas. Thus adapting faster.

So how can you identify a valuable niche today and then learn to pivot when you see that niche drying up? It's about finding the balance in your skillsets. OR if you are focused on a niche for content and go deep, perhaps the skills you use there can be applied to another niche in which you have aptitude and can also go deep.

Managing your ideas and research

I've been exploring different ways to better remember what I read, capture content and organize ideas. There's not one right way and a myriad of tools available. This is a niche in itself. But if you're not keeping an idea file you're missing out as none of us can remember everything nor access it what we didn't realize we wanted to access.

There are many different ways to capture ideas. You need to do what fits your lifestyle and how your brain connects things together. James Altucher, who has a worthwhile read in Choose Yourself, is known for carrying around a basic pad to write 10 ideas per day. Most are bad but he does this to strengthen his mental muscles. It increases his odds of uncovering great ideas. Just like running three miles per day strengthens your cardio.

It's easy to come up with three or four. But getting to ten everyday forces you to think differently. This is much like the 99 business ideas exercise I reference early on but something you can do everyday. I tried it for awhile and while it didn't stick, enjoy going back and seeing what my brain was thinking at the time.

Paper is a fine tool (Field Notes is cheap, quirky and easy to keep with you) but what if you want to store and search for it? For several years Evernote has been my tool of choice. I store all of the articles I write here along with ideas for future articles in addition to a Google Doc. I confess I haven't been intentional until recently in how I title and tag my notes for the future. Even more problematic is the enormous library of images I've taken over the years, most of which poorly organized by date and image number. Hardly retrievable. How amazing would it be to have these searchable by subject and location?

In May I wanted to find all of the first day of school pictures of my daughter from Kindergarten through Senior Year. Some were easy because I organized them. Yet some were really hard and took me a few hours to find. I found them eventually through determination. It took some sleuthing. This was the catalyst that tipped me into tackling how I do this going forward.

Pocket is a newer tool to capture and store content you find anywhere online. I haven't started using it but am assessing whether it will complement my Evernote experience. Dropbox is a place you can store images and files you want to reference later. It's free for up to 2 GB. There you could keep a running document of ideas. I've used it thus far only to transfer large files to others.

Todoist is an app that integrates with your email to keep you organized. Use it to set objectives and track your progress on your projects. It can keep you from being overwhelmed and spinning. Manage your distractions.

If you're just starting to explore these tools or think about how to manage a portfolio of work and projects, I don't recommend my scatter-shot approach. While I'm now in the refinement stage of corralling my thoughts, content and knowledge, it will pay huge dividends to step back and look at the tools or suite of tools you want to use to manage your digital life. You never know when you'll want to revisit a passage in a book or a random idea and can save so much time and frustration through organization.

You can easily make this a monumental task that never gets done, or chunk it up into snackable bites that you knock off over a couple of weeks.

Go slow to go fast. And don't give up.