Episode 23: Thoughtful Software One Year Later

We're celebrating our one year anniversary of the Thoughtful Software Podcast!

Hosts: Fahad Shoukat and Andrew Wolfe

It’s been one year of the Thoughtful Software podcast. What’s the experience been like so far? 

The amount of people and perspectives we’ve been able to have on the show has been crazy! The podcast has helped us have outside perspective on software, technology, culture, and entrepreneurship as we’ve scaled our business. We’ve been able to speak to so many intelligent people in the tech industry. 

Episodes Mentioned:

The thoughtful software narrative makes so much sense. Our business exists because there’s such a high failure rate in the software industry. If there’s so many thoughtful people in the industry, why is there still such a high failure rate? 

  • Even though people are thoughtful, software is still difficult, it’s hard to get right. In general, you can do so much with software and it is hard to contain it and control unlimited capability. Additionally, there’s people problems. It’s hard to retain people in our field. People are willing to overpay for good talent and it’s hard to compete. When you combine all of these factors, human and non-human, it keeps the turnover rate extremely high.  

Let's go back to why you (Andrew) started Skiplist. What was the moment you had when you knew you had to act? 

  • I (Andrew) knew there were so many people who knew how they needed software to work for their organization, they just needed a service company to be humble enough and empathic for people to be able to see where they’re at, figuring out how to work with them where they’re at. That’s when I knew I had to go out and incorporate.  
  • The people part is so important. It’s not about a specific process, building AI, or making a ton of money. It’s about understanding people’s vision and seeing how we can help people who are struggling in their businesses.  
  • To be able to travel and meet with clients and partners and talk about what software means to them, you find that a lot of people care about software as much as we do. They want good software to be a reality. That’s what keeps me driven, seeing everyone’s software dreams become a reality. Skiplist is going to continue to grow and expand into different things, but as long as we keep true to the mission of transforming the world through thoughtful software, we’ll be able to continue meeting the needs. 

There is a huge need for thoughtful software. If we don’t fix the mess that is current software practices and principles that we follow today, then we’re all going to suffer for it. Software isn’t just eating the world, but eating our wallets. 

  • Software is costing the US at least 75 billion dollars due to re-worked and abandoned projects. The loss is in the trillions for projects that never see the light of day. If we can inch towards a better way of building software, that’s more thoughtful, it would be a tremendous boom for the world economy in general. 
  • Look at the medical devices or the innovations in education that don’t get shipped because of bad software. Every product that could help human life be better or easier or a better reality is unacceptable. We have to put our egos aside and work together to create a better society.  

There’s a lot of software that just doesn’t work well, it doesn’t have a good User Experience. Some software is just horrendous and it’s a complete waste. Then, there’s some software that’s just malicious and shows that the builders didn’t care about privacy or security. How do you write good software?

  • It starts with putting people at the center of everything that you do. When you think about how the users might use the product and take yourself out of it. When you look at it that way, you understand your ecosystem. It’s easier and cheaper to ship a bad product, but you’re harming your users.  
  • Doctors take an oath not to harm their patients. Software developers don’t take that oath. It’s easy to cut corners because of pressure. Instead of looking at how we might be not creating the best product, we’re just plowing through and being thoughtless.  
  • How do you build better software? You stop being thoughtless. Again, you don’t put users at risk, but actively try to help them. We think about them as users. You start with the end user in mind.  
  •  I think other people feel the same way, wanting to put people in the center of what they do. Our episode with Gary Vee spoke into this.  (Scaling Values in Your Org with Gary Vaynerchuk (VaynerMedia))
  • One of the biggest takeaways from that conversation is that people are always watching. If you cut corners, the people around you will cut corners. If we expect our people to be thoughtful, then I have to be extremely thoughtful. Whatever you are, your team is going to be the same.  

Favorite TSP Episodes 

Including the podcast and running Skiplist, what has been your biggest challenge so far (Andrew)? 

  • Aside  from having to be an example to my people, you have to start with conviction. When I have an idea, I push it. It’s hard to move me from an idea. I have major blind spots because of my convictions. I’ve been working hard to see things from every angle and get rid of my blind spots. It’s an art to lead and evolve at the same time.  
  • The second thing I’ve learned is how to delegate. It’s pick your own destiny, picking what you work best at. It never gets easier, just different.  
  • For me (Fahad) we try to focus on people, that in itself is the biggest challenge. How do you grow? How do you add new team members? It’s difficult to navigate through. We’ve made mistakes and learned a lot. We’ve been fortunate to be able to work with talented people who can really power through. 
  • One thing I’ve learned is that people don’t come to work to be entertained, the want learn, to be challenged, solve problems, and work with good people. We don’t need bean bags or free lunches. That doesn’t move the needle for people. Creating a company that revolves around solving challenges with great people is what I want to focus on.  
  • We’ve had such tremendous growth. It comes with its own unique challenges. There are risks in growing too slow. There are risks in growing too fast. I prefer the risks of growing too fast. Trying to maintain culture, excellent deliverables, and a communication chains has been incredibly difficult, but we’ve been so fortunate with the people’ that we’ve hired. 
  • Here at Skiplist, we’re really adaptive. That’s what's needed to make good software. We can think on our feet and pivot. Without that our projects would have a much lower success rate.  


Thoughtful software is an interesting narrative. Do you think that in order to get everyone to think about software more thoughtfully, does it require a fundamental shift, or do we just need to get out and tell more people about it? How do we get our message out?

  • It's bigger than just telling people. From a practices point of view, we’re doing everything you should do, but don’t. The unique viewpoint of people first not software first is something that we’re going to have to convince people to do.  
  • Fundamentally, Engineers are typically not people-people, they’re not normally extroverts. That itself has the developers not thinking about people first, but software first. Getting more people that care about people in the field is going to be a big deal. It’s going to help people to see that EQ is just as important as IQ. The people that have a higher EQ will have a bigger advantage in the future of software because they’re going to be able to build the best software.  
  • If you have a high level of empathy and EQ, you can tap into a large, untapped market. When you put people in the center, the software will follow.  

What do you see as the biggest threat to thoughtful software?

  • Status quo. As people become more tribal, they care less about other tribes. Whether It’s inside the software community or society, how can you have empathy for a viewpoint you can’t even see? As we become more tribal, it’s going to be an issue. We have to come together and really care about people and approach things with empathy.  

What is the future of Skiplist? What’s coming? Where are we going? 

  • What we’re doing is terrifyingly ambitious. There’s a big need for our services businesses. There’s a massive need for well-designed projects that care about users.  
  • I see us adding products to our suite, doubling down on internal platforms to make software more efficient and effective for our clients. I see us becoming more of a product and services business able to meet needs across multiple market sectors and expand into the product space. I see us becoming a more of an initiative-based company. The projects-based work we’re doing now is amazing, but at the same time I think we’re ready, willing, and able to help our customers on their initiatives and help them figure how to install AI and how they might use blockchain across market segments. It’s an underserved market and we’re looking forward to, hopefully in 2020, really moving that way.  We want to help businesses make the right choices, not the convenient choices.  

If you could pick anyone, who would you want to have on the podcast?

  • (Andrew) It’s a tossup between LeBron James and Baker Mayfield.  The technology person I really respect is Ben Horowitz. It would be great to have him on the show.  
  • (Fahad) I agree about Ben Horowitz, it would be great. Not sure about LeBron, but I’d like Steph Curry on the show.  

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Fahad Shoukat
Written by

Fahad Shoukat

Fahad has a B.S. in Electrical Engineering and an MBA. He brings over 15+ years in Business Development, Strategy, Sales, Product, and Marketing in various industries such as software development and Internet of Things (IoT). His experiences have led him on an unwavering pursuit to meet thoughtful people and build thoughtful software.