startups

Relearning Relearnings

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My friend, Reagan Pugh, wrote a great post almost a year ago about the things you know to be true, but seem to constantly need to relearn over and over again. This simple concept of ‘Relearnings’ has stuck with me ever since.

It seems to me, the challenge is rarely knowing the right thing to do, the challenge is doing what you know to be right.

Why is it so hard to do the things we know we should be doing?

I believe that the answer is, as it is to so many questions, structure. We fall back to well-worn paths of least resistance even when we know the outcomes are sub-optimal.

We maintain the friendship that we know is a net-negative on our life.

We continue to eat things that make us feel horrible an hour later.

We escalate fights over inconsequential things.

We stay quiet in the meeting when we know that we really should speak up.

Knowing the right thing to do is really only half of the battle. Yes, it takes a level of self-awareness and wherewithal to realize which actions lead to long-term negative outcomes, but that knowledge won’t ever do you much good if you continue to take the same course anyway.

In an effort to try to curb this tendency to regress from the path I know to be best for me, I have started maintaining a list of my ‘relearnings’. Here are a few of the things that I know to be true, yet still sometimes struggle to implement day to day. I have found that the best way to frame these relearnings are as endings to the statement: “It’s in my best interest to…”

  • It’s in my best interest to get more sleep. I feel so much better and productive when I am getting close to 8 hours of sleep every night

  • It’s in my best interest to exercise daily. If I am going to be at my best mentally and emotionally, it as absolutely a prerequisite for me to do something active.

  • It’s in my best interest to start working on my blog Saturday morning instead of waiting until Sunday afternoon. Leaving it for Sunday leads to anxiety and a lower quality product. (Full transparency: I started this post at 5:08pm on Sunday.)

  • It’s in my best interest to be more productive. I am happier and less anxious when I avoid procrastinating and get tasks off of my to-do list.

  • It’s in my best interest to do something more enriching than simply watching TV after work. Cooking, cleaning, learning. Just spending 15 minutes doing something productive makes all the difference in the world.

  • It’s in my best interest to track my food intake. The benefits I get from increased awareness of what I am eating far outweigh the few minutes it takes me to input my food for the day.

  • It’s in my best interest to prioritize my faith daily. The more I focus on deepening my faith, the better every other aspect of my life is. I’m happier, more fulfilled, less-anxious and there is a 1-1 relationship with the more time I invest in my faith and the more harmonious my relationships are.

Startup Relearnings

I don’t think relearnings are contained just to personal growth. It seems like the entire startup industry is currently grappling with many of the same lessons that should have been forged years and years ago. In an attempt to help us all learn from our mistakes and be better equipped next time we are starting, working at, or investing in a company, I’ve come up with a few entrepreneurship-focused relearnings as well.

  • It’s in a startup’s best interest to get its unit economics right. How did we forget this one? If you don’t get your unit economics figured out early, pouring fuel on the fire is only going to exacerbate any problem that exists. Startups need to grow to succeed and if your unit economics are messed up, suddenly growth becomes the enemy. That is a bad, bad place to be.

  • It’s in a startup’s best interest to go slow to go fast. Figuring out unit economics falls within this, but I think it is worth its own bullet point. The name of the game when building a company is speed of execution, but that doesn’t mean everything should be done as quickly as possible. When it comes to hiring, fundraising, developing a scalable economic flywheel, and getting to know your customers’ needs, it really does pay to measure twice and cut once.

  • It’s in an entrepreneur’s best interest to raise the right kind of capital. Venture capital is not right for every company. Be honest with yourself about the kind of company you want to build and pursue the capital strategy that is aligned with that vision. Bootstrapping, grants, venture capital, traditional debt. One isn’t inherently superior to the other. They are different and they fit best with different kinds of companies.

  • It’s in a startup’s best interest to be disciplined when it comes to cash burn. Cash is oxygen. Cash is at-bats. Whatever metaphor you want to use when cash hits zero the ride is over. Do not pass go. Do not collect $200. The more disciplined you can be when it comes to cash burn, the more chances you have to make something happen. Building companies is about a lot of things going against you. Successful companies stick around long enough for one or two big things to fall their way. You will find startup graveyards littered with promising companies that never made it to that one or two big things falling their way because they just couldn’t keep their burn under control.

  • It’s in an entrepreneur’s best interest to be picky when it comes to investors. The marriage metaphor is cliche, but it’s used so often because it is a good one. If your company is going to be successful, taking money from an investor means that you are going to be embarking on a multi-year long relationship. You don’t have to be best friends, but if you have serious question marks about your ability to work together, you are better off continuing your fundraising process. If your only option is to saddle up with someone undesirable, maybe you need to look in the mirror and ask yourself why you are having trouble fundraising. There are great companies that struggled to fundraise, but more often than not, the best ideas are able to find capital, no matter where they are based.

  • It’s in investors’ best interest to remember that capital is not a sustainable source of competitive advantage. Money is like alcohol. It’s an amplifier. If you are a jerk sober, you are going to be a huge jerk drunk. If you are funny sober, you are going to be a comedian drunk. If your company is a well-oiled cash-burning machine, throwing dollar bills at it is only going to allow you to accomplish that purpose even more effectively. If there is one lesson that the world of tech and entrepreneurship has been in the process of learning over the past year it’s that cash, in and of itself is, is not going to win you the day.

These are a few relearnings that I could come up with. What lessons do you believe the startup world is just refusing to learn? What are some relearnings you are working on making stick in your own life?

Till next week. (Hopefully Saturday morning)


Micropreneurship: What it is, Why it Matters, and What resources are out there

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Last week I wrote about my predictions for 2020.

One of the items I touched on was that we would see a rise in a trend I called “Micropreneurship”

I wanted to write this post to go a bit deeper into this phenomenon and to highlight some of the resources out there for aspiring micropreneurs.

What Is Micropreneurship?

I define micropreneurship as “the process of building a small-scale entrepreneurial endeavor enabled by a new generation of technology platforms and tools”. These aren’t startups. They aren’t investment portfolios.

They are blogs, Shopify stores, and online courses.

They are eCommerce plays, newsletters, and recipe guides.

Some of them are side-gigs. Some of them are full-time jobs.

What all of them have in common is that they are made possible by new technologies and services that are increasing the access people have to entrepreneurship. It used to take time and thousands of dollars to get a small business off the ground. Now it takes the few minutes necessary to sign up for Substack, Notion, or Webflow.

The future is here, it just isn’t evenly distributed. If you knew what you were doing, you could always build a business, but now we have the tools available to make that hurdle so, so much lower.

Why does Micropreneurship matter?

So what? People have always figured out how to start businesses. Why does this new trend matter and why does it need some flashy name like Micropreneurship?

Micropreneurship matters. A lot. The lack of it has been one of the fundamental issues that we have been grappling with as a country over the last decade.

The geopolitical story over the last quarter-century that has had more impact on the way our country looks than any other is the fact that huge swathes of our country feel like they are getting left out of the modern economy. This may be blue-collar laborers feeling left behind by technology. This may be highly-educated urban-dwellers struggling under a mountain of debt who no longer believe that the institutions around them work the way they should.

See the fundamental issue is that the economy changed and people didn’t keep up. A relatively small number of highly-educated or highly-technical workers were able to thrive in this new technology-focused economy, but for a large portion of the general populace, they saw their neighbors driving home in new cars as their own prospects dwindled. Our education system is just now starting to wake up to economic realities that were readily apparent twenty years ago.

But I do not think all is hopeless.

I believe micropreneurship can be the panacea to some of these woes.

Micropreneurship can be an enabling force function that provides access to wealth creation for those that have been left out of the modern technology economy. You no longer need to know how to code to build a website. You no longer need to get a small business loan to open up a storefront. We have the tools and resources at our fingertips to unleash a massive wave of technological democratization the likes of which haven’t been seen since the early days of the internet.

More than just the societal implications, people are yearning for this in their own lives. People want to be their own bosses. To have the flexibility of managing their own schedule. Look at how much remote work appeals to people. Doing the same work they have always done, but suddenly being able to do it from wherever has a massive impact. Just think about the impact that defining the work you are actually doing could have.

Micropreneurship Tools & RESOURCES

I am still learning the ins and outs of this new trend, but I wanted to provide some of the resources I have come across so far for those interested in learning more.

No Code MVP

No Code MVP is a course made by Bram Kranstein to help people learn to utilize no-code tools to ideate and build their first product. If you sign up, you’ll be in good company! I purchased the course recently and I am excited to dive in!

Makerpad

Makerpad is the best resource for learning how to build specific products utilizing one or more no-code tools. The site has hundreds of product tutorials and even offers no-code consulting services for businesses looking to automate workflows. Creator Ben Tossell is definitely one of the kings in the no-code space and a good person to keep tabs on.

JumpCut

Jumpcut offers courses for everything from influencers, to marketers, to passive income generators. I haven’t taken any of their courses myself, but the site was recommended to me on twitter and it looks like a great resource that could be worth checking out.

Shopify

Probably the most important company to the micropreneurship movement. Shopify enables thousands of small business owners to quickly and easily get online stores off the ground. Shopify is a big reason why I believe this trend has the legs to go mainstream.

Squarespace

The fact that you are reading this is a testament to Squarespace’s usability. If I can figure it out, anybody can. This is the third website I have built on Squarespace and it has everything I have ever needed to build and manage my blog.

Webflow

Another one I haven’t used before, but this website builder seems to be getting more and more traction based on its ease of integrations with other products. Another on my list to learn más about.

Notion

If you have spent much time reading this blog at all, you will know of my love for Notion. The swiss-army knife of no-code software. You can do just about anything with this simple and easy-to-use software. Notion sometimes suffers as a jack of all trades, master of none, but when simplicity and minimalism is the name of the day, it is hard to go wrong with Notion.

Airtable

Airtable brought promises of bringing the database into the 21st century. I haven’t done more than mess around with this tool, but I know it is extremely powerful and flexible over a variety of use cases.

Zapier

The ultimate integration tool. Zapier gets your information locked in different applications to talk to each other and can set up seamless automations. Zapier is something that I definitely want to become an expert in as I believe that it opens up a whole world of potential for anything you are building.

I am sure this is not an exhaustive list. I am definitely still figuring out the micropreneurship landscape myself so if you have any other ideas for tools or resources that could be helpful, let me know in the comments!


Things are Looping Up

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Life is about loops.

Sometimes it is easy to make the assumption that life is a series of discrete events and choices. We believe that life is like a stone skipping crisply across the surface of a lake. There is a singular point of contact and then we are just along for the ride until the next point of contact.

This assumption is incorrect.

Life is about loops. The iterative processes and actions that define our life, behavior, and businesses.

Things are rarely as simple as action and reaction. This may occur in science experiments that take place in a closed system. Life is more often a series of interconnected systems where the outcomes have some level of impact upon the next impact.

Think about driving. An action that seems like second nature to most of us is actually a complex loop involving multiple neural and physical systems. You are only able to drive because of the short feedback loops between these systems. Moving the steering wheel causes the car to change direction. This feedback is relatively quick and direct which allows your brain to either A) keep turning or B) stop turning.

A key lesson to be learned from driving and applied widely across our personal and professional lives is that a key to operating a system successfully is to keep feedback loops short and direct.

Shoulda, woulda, OODA

A lot of the modern thinking around loops and systems started by Air Force Colonel John Boyd. Boyd developed a concept called the OODA loop that is still widely utilized in military and business strategy today. It is a decision-making framework whereby decisions are made by constantly cycling through the loop of Observe Orient Decide Act. In aerial dogfighting between fighter jets, the fastest or most heavily armored plane is not who wins, it is the pilot who can react most quickly to changes in circumstances. Utilizing the OODA loop methodology, pilots can cycle through decision trees extremely quickly. Less focus is placed on making the correct decision as is focused on making decisions quickly, examining the results, re-orientating accordingly, and then taking action again.

Sound familiar?

OODA loops and the underlying theory that agility overcomes superior resources serve as the bedrock for modern business strategy and technological development. (For a great podcast and loops about in business, check out this episode of Invest Like The Best)

Why startups win

Agile software development and the lean startup movement are two examples of this kind of thinking. In both cases, the lengths of feedback loops are minimized and decision making is pushed as close to the customer as possible. Resources are front-loaded and experiments are run and re-run so that teams can get feedback quickly and make adjustments as necessary.

This is why startups can go toe to toe against massive incumbents and win. Usually, success isn't a case of simply throwing resources at a problem. Startups beat incumbents because they can act and react so much quicker. By the time that a large incumbent has gotten the ship turned in the right direction, the startup already has such a large headstart that it has captured the hearts and minds of the consumer.

Issues occur when feedback loops are too long. A prime example of this is diet and exercise. We all know eating healthy and exercising is good for us. So why don’t more of us do it? The answer is that the feedback loops are long with these activities. You may not see results from your effort for weeks or months. It is easy to get discouraged while the immediate gratification of Grandma’s chocolate cake is immediately available.

Now, this is a massive issue for my industry.

Why the long pace?

Venture Capital is notorious for having extremely long feedback loops. Those startups that are successful enough to have a positive outcome will often spend 5 to 10 years getting there. And this trend is only elongating as companies are staying private for longer. As such, it will take an EXTREMELY long time to figure out whether your decision to invest in one company or another was the right one. Because the feedback loops are so long, it makes it almost impossible to alter your strategy and adjust.

So how do you deal with these long feedback loops? That is the challenge. Here are some ideas I have come up with.

1) Focus on building a repeatable process

Ahh the classic Erik Berg Process suggestion. You knew it was coming. I’m a big process guy. What can I say? When feedback loops are long, the importance of having a good, repeatable process is magnified. Notice what I said. Simply having a process isn’t enough. First, it has to be a good process. Having a bad process is worse than having no process at all because it will likely either reinforce poor decisions or give you false-confidence about your decisions. Second, it has to be a repeatable process. Your perfect process will do you no good unless it is flexible enough to be applied across different opportunities. It also will do you no good if the process is so cumbersome and painful that you struggle to get other stakeholders, entrepreneurs in my case, to get through it. Having a bad process in venture opens you up for MASSIVE issues. You may find yourself with a due diligence process that is so painfully slow and cumbersome, you aren’t flexible enough to be opportunistic on good deals and, even worse, you may experience adverse selection bias as the best entrepreneurs are unwilling to put up with jumping through your hoops.

What does that good process look like in Venture? Unfortunately, there isn’t a one-size-fits-all solution. What works with one segment or geography may not work for another. But it is something that you should spend significant time and energy being thoughtful about. Don’t do things just to tick a box on your checklist, be purposeful and make sure every step in your process drives tangible value for either you or the entrepreneur (ideally both).

2) Document your decisions

With long feedback loops, it is almost impossible to remember the set of facts or thoughts around a decision months or years later. This makes documentation of the utmost importance. If you won’t know whether a decision was successful or not until years later, you need to have enough documentation to be able to come back to it and review what was going through your mind at the time and how that mapped against how things eventually would play out. Were your assumptions correct? Did you anticipate all the exogenous threats? Was your understanding of internal dynamics accurate in hindsight?

You won’t be able to ask yourself the right questions, much less answer them, unless you are documenting decisions effectively. Note that this does NOT mean that you need to write a novel recounting the most minute aspects of every decision. Remember what I said about having an efficient process? This is definitely a case where more does not equal better. How does the saying go? “It was too hard to write you a letter on one page so I wrote it on four.” As in all other aspects of communication, decision documentation should strive for clarity and conciseness. It is better to write one accurate and poignant page than it is to write twelve that are not. (This is also true in blogging and something that I am desperately trying to get better at.)

3) Audit yourself

Hey, remember when I said that it was important to document your decisions? Believe it or not, that is very much predicated on your willingness to go back and actually look back at your decisions. It is amazing how few people and firms do this. More often the self-analysis only goes as far as: “Decision right = skill. Decision wrong = bad luck”.

Have the courage to look in the mirror at all your mistakes. Go back and try to understand where your head was at the time. Use your clear and concise documentation to figure out where you went wrong and how you can react better in the future. The reasons people don’t do this are two-fold. One, people are lazy and this takes time. Sorry, you are just going to have to suck this one up if you ever want to improve. Two, people don’t like admitting they were at fault for their errors. This intellectual humility is what sets the best from the rest.

4) Measure using an intermittent proxy

If you won’t know if something is successful for a long time, try to find indicators with which to orientate yourself even before something is fully baked. Look at the exercise example I used previously. If you focus on how you look in the mirror, it will be extremely hard to stay motivated. If you instead focus on the energy you feel after a workout or the weights/reps you were able to lift, you will have a much easier time staying motivated. You will see progress all along the way instead of only once you reach your destination.

William at Frontline Ventures has an excellent article detailing how he and the Frontline team utilized the intermittent proxy measure of future financings to measure a company’s success. It isn’t a perfect measure (just ask WeWork), but it was good enough to give a directional indication of whether they were on the same track or not. Based on the data they gathered, they realized that they were missing out on deals because their process was too slow. Accordingly, they adjusted their process to be more nimble so they wouldn’t continue to fall into this pitfall.

Staying in the Loop

Life is about loops.

Observe.

Orientate.

Decide.

Act.

Move nimbly and purposefully. Make sure to pick your head up often enough to adjust your direction as necessary. Design good processes that you can repeat scalably and effectively.

Remember: David beat Goliath.

Speed wins and to be fast you need to be able to design tight feedback loops.