Alumnus and tech giant David Karandish, BSCS ‘05, knows what it takes to be a successful entrepreneur.

Karandish has over 18 years’ experience running startups. He is the founder and CEO of Capacity, an AI-native knowledge-sharing platform. His previous startup, Answers.com, was acquired by a private equity company in 2014 for $900 million. Here, he offers 5 Encouragements for Entrepreneurs.

5 Encouragements for Entrepreneurs

I was recently asked to give a 10-minute keynote to a group of startup entrepreneurs and investors, so I thought back on some of the questions I often get asked.

“David, what should I know today that I don’t?”

“What kind of advice can you give me?”

“You’ve had some successes and some failures, what wisdom can you impart?”

As I reflected on these questions, it occurred to me how often I’ve sought out wisdom from other entrepreneurs, when what I really needed was encouragement. Here are five encouragements that entrepreneurs of all stages can relate to.

Encouragement #1: The Work You’re Doing Matters

I want to encourage you to know that the work you’re doing is important.

I know that as an entrepreneur, you probably don’t lack self-esteem. Anyone who is crazy enough to start a business usually has a fairly high amount of confidence. Today things may be going well for you. Maybe you just signed a big client or secured a key investor. A senior developer you were recruiting just accepted. Your new website is finally live.

But there will come a time when you enter into what can only be described as a dark night of the soul.

You’ll have a co-founder who gives up.

You’ll have a team member that you thought would be the next great thing for your sales department take a job somewhere else for a higher salary.

You’ll have tussles with investors.

You’ll have product deadlines you thought you were going to make but didn’t.

In those dark nights of the soul, when you’re putting in 50, 60, 70 and in some cases 80 hours a week on your venture, you’re going to ask yourself this question:

“Is all this worth it?”

I’m here to tell you: yes, it’s worth it.

Here in St. Louis we’ve had so many companies get acquired, then the brain trust leaves our city. Look at the blueprint we’ve had for turning St. Louis around (credit to Gabe Lozano for pointing this out).

40 years ago our city’s plan was to fix up the Arch and add a stadium.

Don’t get me wrong, I’m a big fan of the Arch and I love sports, but we are still working from a 40-year-old blueprint: clean up the Arch grounds and build a new stadium.

Sure, a new stadium is nice, but if we don’t refill the well by creating great companies that people stick with, this city will not reach the full potential that it could.

Your city needs you to create jobs. Your city needs you to stay after an exit.

Your city needs you to hire local.

So, in those moments when you’re wrestling with questions like, “Can I go through with this? Can I put in this extra hour? Can I stick with my idea? Is it all worth it?”

Remember — you have a chance to help make your city the best darn city in the country.

Well, the second best at least. 🙂

Encouragement #2: Build a Diverse Team with Aligned Values

I want to defy a bit of conventional wisdom for a minute on this one.

When people start talking about what it looks like to build your founding team, conventional wisdom says you’ll want a team with a lot of diversity. To be sure, diversity of socioeconomic status, race, gender, background and skills is absolutely critical and will lead to different perspectives coming to light.

But one thing I think is understudied in the marketplace is the idea of values alignment in your founding team.

When you put your initial team together, or when you’re trying to figure out who that cohort of people will take your company to the next level, what I’ve found is early-stage team members don’t usually bow out because they’re not talented.

If they’re not talented, you wouldn’t have hired them.

They don’t usually bow out because they get recruited by another company, although that happens.

In early-stage companies, I’ve found the people who don’t work out are people who don’t fit the values of the company in the stage that you’re in.

So if you’re a fast-moving startup and you want to crank the proverbial lawnmower up to “rabbit” mode and you bring in someone from a big company with lots of great resume potential, but they think you’re going to be operating in “turtle” mode, it’s not going to work out.

Think through the values your team needs in the stage your company is in, and consider how you might ensure your early team fits those values.

Now, this doesn’t mean everyone is going to be a carbon copy of each other.

For example, my executive assistant Jeremy and I couldn’t be more different from one another.

I’m an extrovert, he’s an introvert. I’m intuitive, he’s sensory.

I’m St. Louis, he’s Kansas City. I hate eggs, he loves them.

Most personality tests — and people who know us — would say we’re very different from each other.

Even though we have very different backgrounds, personalities and skills, when Jeremy and I took a values assessment, 4 out of 5 of our top values were the same.

So hire a diverse team, but spend time leaning in to what your personal and corporate values are, and make sure your founding team has a lot of values overlap.

Encouragement #3: Infuse AI Into Your Business

I fundamentally believe artificial intelligence is changing — and is going to continue to change — the way we work. What do I mean by that?

Every field under the sun — transportation, health care, financial services, retail, and every aspect of our economy will be changed by AI.

If you’re starting a business today and you want it to be around for another ten years or more, I highly encourage you to look into how you can start incorporating AI into your business.

I’m going to double click on three areas of AI to consider applying to your business.

Cognitive Offloading

The first is a term called cognitive offloading, a term that has been garnering a lot of play recently. It’s the idea that you take the things that you think about, your memory, the things in your brain and offload them to another medium.

We started doing this thousands of years ago with writing. Instead of having to remember who paid their taxes or how the last act of the play ends, we started writing those things down so we didn’t have to keep them in our heads. With the advent of the internet, we’ve been able to use search engines for fast facts for a long time.

Increasingly, cognitive offloading is going to allow us to take the skills and tasks we do in the workplace and place them on the machines to go complete.

My startup, Capacity, is in the cognitive-offloading AI space — we provide a secure knowledge-sharing platform to help teams do their best work, by making all your company intelligence instantly accessible.

I highly recommend looking into the cognitive offloading space to see if it can intersect with any of the business ventures you’re involved in.

Image Recognition

The second area of AI I would spend some time in is the world of image recognition.

I just saw an article this morning on how San Francisco is banning the use of facial recognition in policing. Now we can argue whether that is a good idea or a bad idea, but the fact of the matter remains – image recognition is taking on entirely new challenges we haven’t seen before.

Whether it’s identifying which fruit should go to the grocery store or identifying areas of fraudulent transactions or helping vehicles drive themselves — image recognition is powering the next wave of the economy.

I would be taking a look at if there is a way you can incorporate this type of technology into your existing offering.

Reskilling

Lastly, when you think about artificial intelligence, everyone wants to talk about Machine Learning, natural language processing, neural networks, and so on. We talk about all these fun movies and TV shows: Ex Machina, The Good Place, Avengers Ultron, Westworld, etc.

But there’s another important area of our economy that people are just starting to jump into.

It’s this concept of reskilling.

If the AI revolution plays out like we think it will, there are going to be a whole bunch of people stuck in the middle who aren’t old enough to retire and not young enough to have naturally migrated to a different field where their skills could be applied in a new way.

This group of people will need reskilling. They’ll need new 21st-century training, jobs, internships, etc.

If I was starting a business today, this is one of the areas I would be looking at. Is there a way my product or service can help this upcoming cohort of people who need reskilling?

I happen to sit on the board of a company called Varsity Tutors — the largest online tutoring platform in the US.

Varsity Tutors is one of the pioneers in its field as they move from not just helping kids get a better algebra score, but helping adults learn new skills and new trades as they’re trying to prepare for the next economy.

Think about ways you can bring AI into your own work.

Encouragement #4: Pay it Forward

Next, I want to encourage you to pay it forward.

My first computer was an old 486, saved from the dumpster.

My dad’s work was throwing out their 486 machines because at that time the technology was so old they thought it belonged in the trash.

So my dad brought one home and I started learning how to code on this old antiquated machine, which changed the trajectory of my life.

The sad thing about where St. Louis is as a city is that we are a tale of two cities. We have a city south of Delmar that has access to immense resources. And yet we have a city north of Delmar whose resources are very much in want.

I don’t want to turn this into a political discussion. I need more than one post for that. But I truly believe that if we want to heal the “Delmar divide” we need to heal the digital divide in St. Louis.

One way I’m paying it forward and trying to help heal St. Louis is through a nonprofit I helped co-found called Create a Loop.

Create a Loop is teaching kids computer science with a one for one model. So for every kid from a well-resourced family who wants to learn how to code, we can provide a scholarship for a kid from an under-resourced area who doesn’t have access to computer science education.

I’m not saying we’re going to solve every problem in this city by teaching kids to code, but I can tell you that we are already starting to put a dent in that digital divide.

We have our first kids in Create a Loop who are starting web-based businesses with what they’ve learned in these classes.

STL friends: If you ever get a chance to volunteer, go to createaloop.org and sign up. Or, if you have any school connections — for-profit, nonprofit, city schools, county schools — reach out to us. I want to see St. Louis on the map for teaching computer science!

I’ve said this before and I will keep saying it until it changes: in the state of Missouri we teach our kids about two years of earth science. Our kids are learning more about stalactites  and stalagmites than they are about how to code an app that could change the planet.

Even as you’re starting your next venture, think about how you can pay it forward in your city.

Encouragement #5: Build a Rhythm of Rest

My last encouragement is to build a rhythm of rest.

You’ve worked your tail off. You’re super excited about your idea and your venture. You’re passionate about what you can build.

But I want to speak as a bit of an elder statesman at 35.

I remember what it was like to be in my early 20s — bright-eyed, bushy-tailed, excited to go start a new venture.

I’m still very excited. I’m even more excited about the work I’m doing today. I’m like a kid in a 35-year-old body. My wife reminds me of this all the time.

I put in lots of hours working at my startup — and I enjoy doing so.

But one thing I’ve learned is that it’s important to build in a rhythm of rest.

When I first started out as an entrepreneur, I’d work seven days a week. Burnout was a regular inevitability.

As a practicing Christian, I’ve started really embracing an old concept called the Sabbath.

Now, people practice this in a lot of different ways, but I choose to take an email sabbath.

Email is the gateway drug of work and Slack is the crack of work.

Go ahead and quote me on that one.

I will work very, very hard six days a week — but from Saturday afternoon to Sunday afternoon, I do a 24-hour email and Slack sabbath.

If something is on fire, you can call me. I’m not that legalistic about it. But I’ve set up this rhythm in my life so I can spend time with my family and recharge.

I do this so I can do a much better job the six days of the week I do work.

Regardless of your faith background or your personal convictions, I would highly recommend building a rhythm of rest in now as you’re starting your venture.

Don’t wait till it’s too late and you’ve already burned out.

To recap, here are my five encouragements:

  1. The Work You’re Doing Matters
  2. Build a Diverse Team with Aligned Values
  3. Infuse AI Into Your Business
  4. Pay it Forward
  5. Build a Rhythm of Rest