Ask your CEO ANYTHING | Upside #100

Strategy

19 Aug

We Let Our Team Ask Us Anything

No agenda, no script. We handed the mic to our own team at our Cambridge countryside retreat and told them to ask us anything. What came back was funnier, and more honest, than we expected.

In this episode: Ali and Zamir take questions from their own team, on biggest regrets, cash flow, giving up control, and what it actually takes to succeed as an Amazon seller.

Key takeaways

The team's collective wins, not any single deal, is what both founders point to as the company's biggest success. Some of the brands they work with achieve more through This Way Up than through all their other global channels combined.
Their honest biggest regret isn't a bad decision, it's how long they've each struggled to let go of rejection and impatience with how long things take to build.
Growth has repeatedly meant deliberately going into the red: every time they choose to invest in growth, cash flow dips for a period. It's a conscious bet, not a mistake, and it's happened multiple times.
The hardest thing to give up control of as a founder isn't strategy, it's small operational stuff, specifically email and travel booking, because scaling means handing over anything that doesn't strictly need the two of them.
Asked what founders actually contribute day to day, the answer wasn't execution: it's vision (deciding where the company is going), living its values, and giving the team explicit permission to make mistakes.
On what a successful Amazon seller needs: product quality is non-negotiable and can't be manufactured by an agency, and resilience is the personality trait that matters most, because setbacks are guaranteed.
Neither founder describes ever having a genuine "we've made it" moment. They run on what one of them called a gap and gain mindset, setting the next goal before the current one is even hit.

Timestamps

00:00 — Cold open: if you could ask your boss anything
00:20 — Ben's questions: biggest success and biggest regret
00:37 — Biggest success: the team, not any single deal
01:18 — Biggest regret: not letting go of rejection fast enough
05:53 — Why we do this: building, the team, and retiring their parents
08:34 — Where we see This Way Up in five years
10:07 — Which markets we'd expand into next
13:36 — Would we have started this, knowing what we know now
14:38 — Did we expect to have a 20+ person global team
15:52 — Why the team's talent is what makes the results possible
17:02 — Have we ever had a "we've made it" moment
19:46 — Has This Way Up ever been in the red
21:29 — The hardest thing to give up control of, as a founder
22:58 — What we think we actually bring to the team
24:14 — How hard it was giving up creative control
25:19 — The one trait every successful Amazon seller needs

The detail

The real answer to "what's your biggest success"
Asked point blank, the answer wasn't a campaign, a client, or a number. It was the team itself, the cumulative effect of people who, on some accounts, generate more for a brand through This Way Up than that brand's entire other global marketing combined. The flip side, the honest biggest regret, wasn't a bad call either: it was impatience, specifically how long it can take to get somewhere even when the direction is right, and how hard rejection is to shake off quickly.

Why growth always means going into the red
Asked directly whether the company has ever been in the red, the answer was immediate: yes, multiple times, and for extended periods. The pattern is consistent: every time they choose to invest in growth, cash flow dips for a while as a direct result. That's treated as a deliberate bet weighed against confidence in where the business is headed, not a warning sign, though both founders admit it doesn't feel good while it's happening.

What founders actually give up, and what they actually bring
The hardest things to hand over as the company scaled weren't the big strategic calls, they were small, personal tasks: email specifically, and travel booking, something one of the founders had genuinely enjoyed doing. The logic for letting go is blunt: anything that doesn't require the two founders specifically should be handed to someone who can do it, so their time goes to what only they can do. Asked what that actually is, the answer was vision (deciding where the company is going, not just what happens day to day), living the company's values visibly, and explicitly giving the team permission to make mistakes rather than fear them. A related, harder version of that same letting-go showed up when creative control was handed over as the design team grew, described as building a mosaic where the founders set the vision and create space for everyone else to add their own piece, rather than trying to make everything themselves the way a founder-led business often starts out. The same theme of handing off control as a team scales globally comes up in How We're Building a Global E-Commerce Team.

What it takes to succeed as an Amazon seller, and why "we've made it" never really arrives
Asked what separates sellers who succeed from those who don't, the answer split into two parts: product quality, which is treated as completely non-negotiable and something no agency can manufacture on a brand's behalf, and resilience, the personality trait both founders landed on because setbacks on Amazon are guaranteed, not a possibility. That same restlessness shows up in how they talk about their own progress: neither describes a genuine "we've made it" moment, instead running on a mindset of setting the next goal before the current one is even reached. It's the same tension between ambition and satisfaction covered from a more personal angle in Founders' Freedom: Ali & Zamir on Living Life By Design.