This week on Random Access Memories, I’m diving into my conversation with Rinki Sethi (CSO at Upwind). Rinki has spent almost 25 years in cybersecurity, working everywhere from Walmart and eBay to Palo Alto Networks, Rubrik, Twitter and Bill before becoming CSO at Upwind. She’s also somehow found time to start her own VC fund. But this wasn’t really a conversation about her resume We talked about the mentor who stopped her leaving cybersecurity, why the people you work with matter more than the logo on your payslip, what great leadership actually looks like, taking career risks and why investing in relationships might be the best career investment you ever make.

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Chase people, not logos.

Rinki nearly left cybersecurity early in her career. Then she joined Walmart and met a mentor who took her under his wing, taught her the technical side of security and helped her discover what she actually loved about the industry. More than 20 years later, she still points to that relationship as one of the most important moments in her career. Her advice to people starting out is simple. Stop chasing the biggest company name you can put on LinkedIn. Find people who will invest in you, let you make mistakes and genuinely want you to succeed.

Great leaders want you to become better than them.

I loved Rinki’s definition of a good leader. Someone who wants to see their people grow, isn’t afraid to give difficult feedback and genuinely wants those people to eventually become better than they are. This one really resonated with me. Some of the things I’m proudest of in my career aren’t security programmes or certifications. They’re people I hired at junior levels who are now CISOs and VPs. If someone eventually has to leave your team because they’re ready for your job, that’s not a failure. That’s the job.

Leadership isn’t building followers. It’s building people who eventually don’t need you.

AI makes bad processes fail faster.

Anyone can build now. That doesn’t mean everyone will build something good. Rinki believes leaders need to get closer to the technology again because AI is moving too quickly to lead it from a PowerPoint deck. You don’t necessarily need to spend your evenings writing Python, but you do need to understand what you’re trying to achieve, how the pieces fit together and what good looks like. Otherwise AI just gives you an incredibly efficient way of doing something stupid.

Automating a shit process doesn’t make it a good process. It just makes the shit happen faster.

If your next job feels exactly like your last one, why are you taking it?

After multiple big-company CISO roles, Rinki was about to sign up for another one. There was nothing wrong with the opportunity. She just wasn’t excited about it. It felt like doing the same thing again. Then Upwind came along. Smaller company, completely different environment and a role that stretched into product, marketing, customers, security and IT. She chose the option where she had more to learn.

Being comfortable feels great. It’s also usually a sign you’re not learning very much.

Build relationships before you need them.

Rinki finished the episode talking about something I completely agree with. Make time for people. She’s had board positions, investments, jobs and opportunities come from relationships where there was absolutely no obvious return when she first made them. That’s the bit people get wrong about networking. If you walk into every room wondering what everyone can do for you, people can smell it. Meet interesting people. Help them. Stay in touch. Become part of communities. Most of those relationships will never turn into anything transactional, and that’s fine. Some will change your life five years later.

The best time to build your network is when you need absolutely nothing from it.

The most important decision you make when taking a new job might not be the company. It might be your boss. Rinki nearly left cybersecurity early in her career because she hadn’t found the right environment. Then she joined Walmart.com and met someone who invested in her, taught her, challenged her and gave her space to make mistakes. More than 20 years later, she can still trace much of what came afterwards back to that relationship. It’s why she tells people starting their careers not to obsess over getting into the biggest company they can. Find the person who is going to make you better.

Companies change. Titles disappear. That amazing logo you were desperate to put on LinkedIn eventually becomes another bullet point on your resume. The people you meet along the way stick around much longer.

Why did I join Gambit? Because I believe Curtis Simpson can teach me a whole new set of skills and challenge me in new ways. I love the product. I love the founder team. BUT the person I’m working for made me sign the contract.

A great company might change your resume. The right person can change the rest of your career. Choose people wisely.

This week’s conversation with Rinki got me thinking about the people who quietly change the direction of our careers.

Early in my career at NCC Group, my manager was Ben Jepson. Looking back, he was probably the most foundational mentor I’ve ever had. He constantly gave me challenges that felt slightly beyond what I was ready for. He sent me around Europe, over to the US and at one point to Jordan. Every time I started getting comfortable, there seemed to be another country, another customer or another problem waiting for me.

At the time, I probably just thought that was the job. Looking back, I realise Ben was giving me something much more valuable. He was giving me opportunities to grow. He trusted me with things before I necessarily knew I was ready for them, then gave me enough space to figure them out for myself. A huge amount of the confidence I carried into the rest of my career was built during those years.

But the biggest thing Ben taught me wasn’t technical. He taught me what a mentor can do for someone’s life. When somebody invests their time in you, challenges you and believes you’re capable of more, you carry that with you. It’s why I've always tried to do the same for the people I've managed since. I can never really repay Ben for what he gave me, but I can pay it forward.

Give people opportunities before they are ready:
Some of the biggest growth in my career happened because someone trusted me with something difficult and let me work out how to deliver it. If you only give people opportunities once they've already proved they can do them, you're not really giving them an opportunity to grow.

Great mentors become part of how you lead:
The best lessons aren't always things someone explicitly teaches you. Sometimes you realise years later that you've started treating people the way somebody once treated you. Ben's investment in me didn't stop when I left NCC. I've carried pieces of it into every team I've built since.

Grattitude is something you pay forward:
There are people in all of our careers who opened a door, took a chance or saw something in us before we could see it ourselves. You might never be able to repay that person directly. You don't need to. Find someone coming up behind you and do for them what somebody once did for you.

The best mentors don't just change your career. They change the careers of people they'll never meet, because eventually you become the person opening the door.