This article features highlights from episode 8 of our podcast, The Abstract. You can listen to the full conversation here.

Gary Spiegel’s early days at the Federal Reserve Bank were marked by an intrinsic fascination with business law, ethics, and using legal prowess to shepherd enterprises responsibly.

Fast forward to Silicon Valley in the late '90s, when it was the heyday of tech startups. In a bold move that would shape his career path, Gary took the leap into tech, sending cold letters to tech companies in the Bay Area, after which Adobe recognized not just his skills but his untapped potential and passion for growth.

‍“I was really thankful that somebody saw something in me. The one thing that I've held onto for my whole career is that I've been lucky at different points where people were willing to take a chance on me without knowing my skills necessarily.”

From then on, Gary's journey was marked with constant constant change, challenges, and above all — triumphs. He went through two company acquisitions in two years at MySQL, then joined Anaplan where he helped them go public, then again private.

We had the chance to speak with him and uncover his journey on our podcast, The Abstract. In this article, we’ve outlined some of the highlights from our conversation.

Take a leaf out of Gary’s IPO readiness playbook

Gary's IPO journey was born out of a deep-rooted aspiration. This motivation acted as a powerful catalyst, propelling him to steer Anaplan towards becoming initial public offering (IPO)-ready.

One of the steps in this process was the pre-IPO readiness exercise.

“We would do a shadow session where we’d sketch out what the IPO would look like, the team contributions that we would need, etc. Because you have to be ready on the accounting as well as the legal side.”

As Gary delved into the complexities of the IPO landscape, he encountered a mindset shift. The IPO preparation called for an acute awareness of what the legal’s role was going to be.

"I had to really be responsible about how I'm staffing, and what the needs are. We were talking about what our earnings calls were going to look like. I had never been part of an earnings call before that. So, this was a major learning curve."

This steep learning curve prompted Gary to absorb as much knowledge as possible. He sought insights from mentors and leaned on the support of their outside counsel to bridge the knowledge gap.

“We had great outside counsel. Gunderson Detmer was our chief corporate counsel, so having their support helped me as a first-time IPO GC. I could always go to outside counsel for some technical advice. We also hired an excellent SEC reporting governance person before the IPO, who was able to do all the things that I had not done myself, like ask the right questions about how you set up the equity programs in a way that you're going to report on them correctly.

I finally reached a point where I was able to be the person that could help the executive team understand where the IPO was going, what we needed to watch out for, and be responsible about how we communicate our business.”

During the IPO hustle at Anaplan, Gary recognized the significance of relationships and influence.

"There were times where I felt that since I didn't have IPO experience, I didn't have the same weight of credibility to say, ‘No, that's not really appropriate.’ But I knew I had to go in, and a lot of it was 1:1 conversations about how IPO plays out, whether it’s worth being too aggressive on something, etc. All those things are relationship-based; they're not necessarily skill-based.

In any of these really difficult transactions, there's a certain element where you don't have time to get up to speed, so you hope you have a minimal understanding. So, being an expert in the business and having good relationships with the key people counts for a lot more in my book.”

The IPO journey, he found, wasn't solely a technical feat. Instead, it hinged on the ability to think swiftly about the business's best interests and align the executive team with the broader strategy.

Gary also highlights the delicate balance between technical expertise and relationship-building.

"There's the technical expertise, and then there's the influence and relationship side. GCs need to have a little bit of both, but I think tilting towards the relationship side helped a lot in my experience with the Anaplan IPO."

How project management drives IPO success

In the high-stakes world of IPOs, maintaining operational precision is paramount.

The question often arises: Who is responsible for ensuring the operational parts of the IPO?

"It was legal! The people who knew about the IPO knew my life was just checklists at that point. It was like a NASA mission; you just run through the checklist every day. But it took some thought to put the checklist together, and it was constantly evolving. Every day I'd say, ‘Here's the portion of the checklist that needs to be done,’ and evolve into separate checklists for each item."

Gary reflects on this approach, emphasizing the need for a project management mindset.

"You have to have a project management mentality. That's one area where I wish we had invested more—having an actual project manager. We shared the function between legal and finance, but legal took the biggest brunt of it. But that was how we got it done. So, I'd have a checklist for all the HR matters, a checklist for exec comp, a checklist for S1-related things, etc."

The project management approach allowed for a structured and organized process that left no stone unturned.

The dual role of in-house legal counsel in driving acquisitions

But before Anaplan, Gary's journey into IPOs and acquisitions began at MySQL, where his team went through not one but two different acquisitions subsequently.

The journey from MySQL to Sun Microsystems to Oracle

The acquisition journey was not without its trials, starting with (temporarily) saying goodbye to his dream of going through the IPO journey at a company.

“When Sun Microsystems bought MySQL, it took away the IPO. That added a lot of uncertainty to my own career trajectory. At that juncture, I wasn't sure I made the right decision, jumping from a stable company like Adobe. And then, during the 2008 economic upheaval, Sun lost a quarter of its customers overnight because of the financial difficulties. It was a very challenging time.”

With Oracle's subsequent takeover, the complexity of regulatory hurdles and industry dynamics further intensified. In such testing times, Gary adopted a "what happens, happens" mentality.

‍“We would joke on the MySQL team; we made t-shirts, ‘Two acquisitions, two years, billion-dollar company.’ At that point, you could only laugh. You would never plot that out for your career. But I have to say that it was a formative experience. One of my managers at Sun was very calm and level-headed and always said, ‘Hey, this is Silicon Valley. These things happen. You may not be prepared for it, but you have to know it's going to happen.’”

Despite the whirlwind nature of acquisitions, Gary's emphasizes the intellectual satisfaction that accompanies such transformative events, due to the invaluable role legal counsel plays in shaping the outcome.

“As lawyers, we have a great opportunity to be part of these formative events in a company's history. To me, that was really impactful because once you take the emotion out of it, to the degree that you can, these things are very intellectually satisfying. They're very professionally satisfying events. They're things you can really learn from.”

Thoma Bravo’s acquisition of Anaplan

Later, at Anaplan, Gary helped the company through a blockbuster take-private transaction when Thoma Bravo acquired them. During our conversation, he highlights the strategic considerations involved in take-private transactions. While IPOs emphasize broad public engagement, take-private transactions hone in on a single buyer.

“On the take-private side, your purchasers want growth, but it's not the broad public markets. So, it feels a little different. You’re targeting a single buyer rather than the mass public set of potential investors. It's less of a marketing thing. So, the approach is not about selling the business and the relationships; it was more about making sure we're describing the business correctly, doing the due diligence, making sure that the valuations of the company are on point.”

In-house counsel's role in navigating the public to private complexity

For in-house legal counsel, take-private acquisitions require them to play the dual role of strategist and communicator.

"It's really about making sure that when the shareholders vote, they have all the information they need to make an informed decision, and you're making the best recommendation. They're going to get their payout after that, and that's the end of that relationship with those investors. So, it's just a different way of looking at things." 

Achieving skill–culture balance when hiring in a public vs. private company

Hiring for legal teams in public and private companies involves distinct considerations. At Anaplan, Gary describes the initial hires were around handling revenue contracts, a reactive strategy to meet immediate needs and “keep him sane”.

“I didn't have a great strategy there, to be candid. In hindsight, I'd probably think about doing things a bit differently in the sense that I'd think more about multipurpose players. Because when you're getting into the series D, E, and F type of scenario where you're not sure exactly what you're going to need, you need people who are flexible, can react quickly, and are willing to jump in on unknown things.”

Striking a balance between skills and cultural fit emerges as a cornerstone of Gary's approach. He emphasizes his preference for creating an environment where people feel empowered to express their growth aspirations.

“As we got closer to the IPO, I knew that we needed specific skill sets. We needed somebody who was dedicated or knew a lot about privacy or product development. But I also really tried, as a manager with a growing team, to be conscious of the fact that it’s important to be a manager who is understanding and forgiving and is interested in their team’s growth as a whole.”

For Gary, hiring extends beyond qualifications; it's about hiring individuals who contribute to a workplace that feels like a second family, regardless of whether it's remote or in-person.

“I would always prefer hiring people who make the workplace feel like a better place to be than just focus on the skills, whether it’s remote or in person. You’ve got to invest in building that kind of cultural tightness.”

In the realm of public companies, the focus evolves further.

“Once you get into the public company side, you also have to focus on redundancy or ability to scale at the right time, but not overspend on hiring. Hiring becomes much more tactical, but you still have to hire the right fit for your team. It was like we were more constrained because we were a public company, and the G&A spend thresholds became more important.”

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As the leader of a legal team, Gary envisioned a micro-level growth path. This approach aligned with the larger corporate culture and the aspiration for individuals to evolve within the company.

To listen to more of Gary’s insights from his experience enabling M&A and IPO transactions, building a team of 20+ members, and more, check out the full conversation on The Abstract.