How to scale yourself as a founder

Scale more than just your business

In Silicon Valley, "scale" may be the most cliched of startup topics – headlining a thousand medium posts, generic theme to any given podcast episode, title to many mediocre panels. It's easy to eye roll if you're just watching the spectacle.

But for early stage founders, scale is a painfully real challenge. Too often, scale is sacrifice. I certainly lived that in Lever's early days.

I was recently invited to speak to a group of 16 early stage founders, but not just any founders. This was a cohort of female Canadian founders with limited capital or whose businesses had been 100% bootstrapped to that point. They came to Silicon Valley for access to the capital networks that remain elusive to "outsiders." Some were a few months in, some had been operating for years. None had the luxury of big teams. For early stage founders facing that kind of reality, what advice on "rapid growth" and "scale" is helpful and authentic?

Of course you must scale your operations, your team, and your customer base, but pulling off scale goes way beyond just the business. If you scale your business without also expanding your vision (your addressable market, your product lines, in short - your ambition), then a founder might find themselves operating a nice medium-sized business but not a category winner.

Scale must apply in 3 dimensions:

1. Scaling your business
2. Scaling your vision
3. Scaling yourself

The easiest one for a founder to miss is scaling themselves. In today's warped "hustle culture," it's too easy for a founder to convince themselves that it's their duty to grind and it can feel irresponsible to do anything but grind. There's always too many needs for a founder to address everything, so getting your business to the next level of scale involves being extremely strategic about how you and your team spend your time. That sounds nice. But what the hell does that mean in practice and how do you identify the most strategic needs?

Scaling yourself

I've personally embraced wisdom from Roli Saxena (a stunning operator whose experience spans LinkedIn, Clever, Brex, and more). She follows a framework that was popular among execs at LinkedIn that helped her rethink how she was spending her time and what "being strategic" really means.

“Leaders can fall into this pattern feeling like your time belongs to your team and you should never say no or be unavailable. What a waste of human capital! Leaders should be building strategic initiatives and need the blank space in their calendars to do it.” – Roli Saxena

For a founder facing scarcity of time and attention, they have to constantly edit and choose to spend time on the most strategic things, but what does that even mean? Everyone can agree that tasks should be evaluated on their Impact, but another dimension that I think is clarifying for leaders is "LIkelihood of Success."  At the outset of an initiative, a founder has an intuition about whether something is likely to succeed — maybe because you've run an experiment beforehand, or you have past experience in that area.

It can seem logical to focus only on those initiatives that are both "high impact," "high likelihood of success" — what Roli calls "Home Runs."
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When an initiative has a high likelihood of success, it's probably not that risky. It may be quite hard, or it may be the most energizing, and it most likely has a critical company need attached to it... but in my opinion, a founder/CEO makes their biggest contribution when they apply themselves to high-risk, high-reward decisions in areas with a lot of uncertainty -- those in the "High Impact" but "Likely to Fail" quadrant. These initiatives are rife with non-obvious decisions that require a founder's deep bench of knowledge and honed intuition, and the results of which often lead to company-defining moments. I call these "Strategic Initiatives," and believe this is where leaders should devote the majority of their time. Essentially, they're only "Likely to Fail" without a founder's efforts.

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Truly scaling yourself

Moreover, there's an even bigger opportunity here. In leading a team of any scale, but especially true at the very beginning, the only way to truly scale yourself is to grow your bench of talent. It's not enough to hire them, you also need to path them towards taking on ever-bigger roles and responsibilities. Those "HIgh Impact"/"Likely to Succeed" initiatives are exactly the type of experience that grows talent within your team. Delegate them. If you don't, you'll be sorely lacking in talent you can trust when you truly need it down the road.

In delegating the Home Runs to others, you're not only sparing yourself the stress of overwork, but also fulfilling a critical leadership responsibility. While the team executes on the present, a founder/CEO is needed in the future. You might be the only one thinking about the risks and opportunities 6, 12, 18+ months ahead. That can make the difference between a company that grows incrementally over time, versus the one that truly manages to achieve rapid top-tier growth. Creating space for yourself to anticipate the company's future needs is actually part of the job; and it's essential not just for scaling your company, but also for scaling yourself.