Today on Next Level, Zach talks to Sascha Goldsmith, the Quantum Knight’s CTO.

Sascha shares about his unconventional path to becoming a CTO, shaped by self-taught experiences and diverse professional roles. From his early introduction to programming at age seven to post-college training at Price Waterhouse, Sascha’s journey reflects a commitment to continuous learning and adaptation. Transitioning through various companies and roles, Sascha accumulated experiences in startups and managerial positions at Amazon, ultimately leading to his current role as a CTO in a quantum cryptography startup.

Sascha’s narrative emphasizes resilience, problem-solving skills, and a willingness to learn from setbacks as essential qualities for success in the technology industry. Aspiring technologists are encouraged to embrace unconventional paths and cultivate a mindset of lifelong learning to navigate the dynamic landscape of technology effectively. If you’re looking to take the next step in your career, Sascha’s suggestions are invaluable.

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The Next Level Series:

Next Level is a Videocast for Aspiring Engineers with Keyhole Software’s Chief Architect, Zach Gardner. This series dives into the pivotal question every software engineer faces: what direction should my career take?

Like many of us, Zach grappled with this dilemma until he found guidance from incredible mentors. Now, Next Level brings these insights to you. Zach interviews tech leaders, delving into their diverse career paths and success stories. Spoiler: careers in tech rarely follow a straight line! Discover the stories, challenges, and strategies behind these industry giants, all aimed at helping you map out your own journey.

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Partial Episode Transcript

Note: this transcript section was created using generative AI tools like YouTube automated transcripts and ChatGPT. There may be typos, slight content changes, or character limits for brevity!

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Zach Gardner: Ladies and gentlemen, welcome to the future. I’m Zach Gardner, the Chief Architect at Keyhole Software, and I’ve been very fortunate to have some amazing mentors in my career. I’ve learned from some awesome people and met some interesting characters, but I’ve also encountered some not-so-nice individuals. I try to learn from all of them, understanding not just what they’ve done in their careers but also why they did what they did and how they were successful. I felt it was selfish to keep all these lessons inside my cranium, so I decided to start this videocast, “Next Level,” to talk to other people who have had similar or different journeys than mine. I want to figure out what they’ve learned in their career paths that could potentially apply to the next generation of technical leaders. I want to ensure that when I retire, I can be on a beach in Hawaii without worrying about production issues.

Today, with me, all the way from beautiful Detroit, Michigan, is Sascha Goldsmith. What’s going on?

Sascha Goldsmith: Very great to be with you, Zach. Super honored. Your comment reminded me of a quote from Isaac Newton: “If I see further, it’s because I stand on the shoulders of giants.” We all have so much to learn from each other.

Zach Gardner: That’s actually my second favorite quote from Newton. My first favorite is when the apple hit his head, and he said, “Ouch.” It’s the most famous four-letter phrase ever, with a lot more gravity.

Sascha Goldsmith: (laughs) There we go, some puns, and we’re not even two minutes in. Alright, I’ve got to get my disclaimer out of the way. (in radio voice) All views and opinions expressed in this program are those of the participants and do not reflect their employers, trade organizations, any car magazines they might subscribe to, or any loyalty programs from grocery stores. We’re just two dudes talking. I think you’re actually the first CTO I’ve had on the program, so a very warm welcome.

Zach Gardner: To get people started off, could you talk a little about your career journey? What are some of the places you’ve worked at, projects you’ve been on, and do you remember the very first thing you programmed?

Sascha Goldsmith: I definitely do. I actually brought a prop here. This is the oldest programming book I have; it’s called “Subroutines and Secrets,” written in Apple BASIC. I have to confess I don’t look at it much anymore since no one uses Apple BASIC, but it was a big part of my early life. I never took a computer science course and taught myself programming from age seven. That book, I got at age ten. My absolute first program was from that book. It gave me the tools to make my first program, and that’s a good lesson for anyone: you’ll rarely get the entire answer delivered; you’ll just get tools and hints.

There used to be a program called Copy 2 Plus, which theoretically let you copy from one floppy drive to another. I loved the menuing system and what it could do. I wrote an Apple BASIC program over a few months, taught myself BASIC, and that was the absolute first program I ever wrote. I used it all the time to manage my files.

After that, I had a second college experience with Price Waterhouse, where I spent three months training after college to learn real computer programming. Then I moved to a cryptography startup. If you’re interested in the craziest technical thing I’ve ever solved, it was hardcore cryptography where a single bit getting mangled rendered the whole stream useless. Under load, it would fail, but it worked in all my tests. It turned out the physical machine had a defect in its RAM. It only happened under load in the upper memory, and once we figured that out and ran it on a different machine, everything was fine. That was the craziest thing I’ve ever solved early in my career.

From there, I worked through a series of companies as an architect (though I’m not sure what that means). Eventually, I landed at Amazon, moving from an IC to a manager, leading their seller website’s enterprise security teams. Now, I’m a CTO at a startup doing quantum cryptography. You never know where your journey will take you. It’s always fun being on the journey, and sometimes you have a destination in mind, sometimes you don’t. Take the opportunities life gives you because they come around infrequently. It’s a combination of luck and hard work that makes it happen.

Zach Gardner: That’s a common theme with the people I’ve interviewed. Rarely does someone’s career journey resemble anything close to a line or curve; it’s almost always a wave of ups and downs. As long as you have a firm foundation, diligence to understand programming, and openness to opportunities, you can succeed. The story about the RAM is interesting. One of the principles instilled in me early in my career was, “Don’t blame the compiler; it’s your problem.” It takes experience and seasoning to recognize something’s wrong with the machine. How did you discover it?

Sascha Goldsmith: We didn’t have Stack Overflow back then, but we had the original Sun forums, which were a wonderful community. However, they couldn’t help because it wasn’t a software issue. It was like the movie “Apollo 13,” eliminating every possible cause until you find the actual problem. It took weeks, but eventually, you realize it’s a hardware issue. Nowadays, in a cloud server, you could probably get another AMI without the RAM issue and be happy, but dealing with a physical machine with a hardware issue is a different challenge.

Zach Gardner: My craziest issue was with a web-based application interfacing through a Java applet with legacy code. Sometimes, when a series of conditions were met, the app would just die. We traced it to a thread or pointer in the Windows application that didn’t deallocate correctly. The weird part was, if you minimized the window and then opened it back up, everything was fine. It’s hard to describe the amount of ESP you develop working on these systems. It’s something you can only gain through hard work.

Sascha Goldsmith: The dumbest thing I ever did was a simple integer to pointer conversion while working on Amazon’s help system. It tested fine but crashed under load due to the volume of hits. Within hours, the help system was down. I owned up to it, put in the fix, and retested it thoroughly. Those moments where your heart rate goes up remind you we’re human and make mistakes. You try to eliminate as many as possible, but they still happen.

Zach Gardner: Let’s pivot towards cryptography and quantum technology. I admit I’m not well-versed in it. Could you share your experiences with this technology and where you see it going in the next few years?

Sascha Goldsmith: There’s an open debate: it could either completely change the world or never fully materialize due to error correction challenges. In cryptography, quantum computers can potentially solve two main problems better than classical computers: Shor’s algorithm for asymmetric cryptography (public-private keys, signatures, blockchain) and Grover’s algorithm for symmetric cryptography (AES, DES).

The fear is that nation-states or criminal syndicates might already have the capability to break some of this cryptography or that they are storing encrypted text to break in the future. My recommendation is to start thinking about moving beyond 256-bit symmetric cryptography. Current algorithms like AES max out at 256 bits due to performance penalties at higher bit sizes. The government is challenging the cryptographic community to develop algorithms with higher bit sizes that perform well.

Symmetric cryptography might be safe for another 5-15 years, but asymmetric cryptography could face breakthroughs in 1-4 years. Start preparing by considering larger bit-size algorithms and secure sources of entropy. Your data needs to be protected for its entire lifecycle, and it’s important to have multiple mechanisms in place. There’s no silver bullet; even with perfect cryptography, other vulnerabilities like social engineering or malicious insiders can still pose risks.

Zach Gardner: That’s insightful. Even if you have great cryptography now, the exfiltrated data can still be at risk in the future. It’s an attack vector I hadn’t considered.

Sascha Goldsmith: Yes, and that’s why having multiple safeguards is crucial. Good hygiene is expensive day-to-day but necessary. Cryptography is just one tool among many. Losing one of our main tools means we need to look for more secure solutions. Consider the FIPS 140-2 standard for current cryptographic compliance and start preparing for FIPS 140-3.

Zach Gardner: Lastly, what advice would you give to your younger self and those looking to break into technology?

Sascha Goldsmith: I would recommend looking at Amazon’s leadership principles or similar principles from other tech companies. Understand them and how your experiences align with them. Bring notes to your interviews and be specific about your accomplishments. If you’re interviewing for big tech, books like “Cracking the Coding Interview” are great resources.

For managers, the hardest transition is realizing your success is now about your team’s success. Put mechanisms in place that work and continue to let you accelerate your scope.

Tell a story with specifics, highlighting how you’ve demonstrated different leadership qualities. Data and specifics will always be appreciated.

Zach Gardner: That’s great advice, Sascha. Things I wish I had known earlier in my career. Where can people find out more about you?

Sascha Goldsmith: I’m active on various social networks, but I don’t have a MySpace. You can find me on LinkedIn and Twitter.

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