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Inside Airwallex: $1M to $1B Angel Story

May 27, 2025
Jack Zhang on Airwallex's wild scale journey, Stripe deal, and $1B exit losses.
Topics discussed in the episode:
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How to approach taking secondaries as a founder?
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How to manage company finances after significant fundraising?
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What are the benefits of partnering with strategic investors?
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How to sustain rapid growth over multiple years?
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How to build the right team culture and avoid hiring mistakes?
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How to decide whether to accept or reject an acquisition offer?
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How to overcome near-death financial challenges?
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How to find product-market fit when initial products fail?
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How to handle when a VC pulls a term sheet?
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How to secure significant investment with minimal prior relationship?

How to approach taking secondaries as a founder?

Founders may consider selling shares in secondary rounds; knowing when and how is important.

"I recommend founders take enough secondaries so that they can account for life... I think in London, you need like 20 to $30 million to live a very kind of comfortable life."

  • Take sufficient secondary to secure personal financial stability.
  • Ensure that taking secondaries aligns with company's stage.
  • Prioritize company's long-term success over short-term gains.

How to manage company finances after significant fundraising?

Financial discipline is crucial even after raising large sums; overspending can be dangerous.

"I don't know what is financial discipline. So I don't have a budget. I'm just like, hire as fast as possible, blow it all out. And then I realized at one point that we're running out of money."

  • Implement financial controls regardless of capital raised.
  • Avoid over-hiring before establishing sustainable revenue.
  • Monitor cash flow and budgeting to maintain financial health.

What are the benefits of partnering with strategic investors?

Strategic investors offer more than capital; their support can be transformative for your business.

"And after that, they were like, we're going to invest at $1.1 billion, $100 million... Yuri basically didn't ask me anything about my personal about my business. He just asked me a bunch of stuff about how I grew up."

  • Strategic investors can provide unique insights and networks.
  • They may invest based on belief in the founder's potential.
  • Building strong relationships opens new opportunities.

How to sustain rapid growth over multiple years?

Achieving and sustaining high growth rates requires strategic planning and relentless execution.

"We basically never grow below 100% from 2015 to 2023, for eight years straight... And we're still growing 90% year on year last quarter."

  • Consistently focus on scaling strategies that work.
  • Adapt and innovate to maintain growth momentum.
  • Monitor key metrics to ensure sustainable scaling.

How to build the right team culture and avoid hiring mistakes?

Building the right team is crucial; hiring for culture fit and competencies over experience leads to success.

"We hired a lot of people with a lot of great experiences... and none of those people worked... we had to like fire all of them."

  • Prioritize hiring for curiosity, determination, and cultural fit.
  • Experienced hires may not always adapt well to startups.
  • Invest early in building a strong, cohesive culture.

How to decide whether to accept or reject an acquisition offer?

Choosing to accept or reject an acquisition offer is a pivotal decision that impacts your company's future.

"They tabled a $1.2 billion offer... we turned that down... Ultimately we’re going to compete... I think I’m going to give it a shot on this one and put all my life into it."

  • Weigh long-term vision against immediate gains.
  • Consider impact on mission, team, and personal goals.
  • Trust your conviction in your company's potential.

How to overcome near-death financial challenges?

Financial crises are common in startups; overcoming them requires vigilance and adaptability.

"I realized at one point that we're running out of money... We went from like 100 something people to like 600, 700 people in a year."

  • Implement financial discipline; monitor budgets and burn rate.
  • Avoid over-expansion before achieving sustainable revenue.
  • Stay alert to financial health to prevent crises.

How to find product-market fit when initial products fail?

When initial products don't succeed, it's crucial to pivot and adapt to find product-market fit.

"We built an invoicing product... And we just never really get product market fit on that product... We build like peer-to-peer algorithm... We know it's going to fail."

  • Be willing to change direction when products don't gain traction.
  • Continuously test and validate ideas with customers.
  • Persistence is key in the journey to find PMF.

How to handle when a VC pulls a term sheet?

Experiencing a VC pulling a term sheet can be disheartening, but knowing how to navigate this setback is essential.

"One of the VCs actually believed in and actually wanted to write a check and lead the round... they give the term sheet, they signed, and they took it back."

  • Always have backup options when fundraising.
  • Maintain conversations with multiple investors.
  • Resilience is key; setbacks can lead to better opportunities.

How to secure significant investment with minimal prior relationship?

Securing investment without prior relationships is challenging but possible if you communicate your vision effectively.

"And she's like, how much money are you raising? I'm like, I'm probably going to raise a million US. And she's like, what about if I give you $2 million?"

  • Communicate passion and vision convincingly to potential investors.
  • Opportunities can arise unexpectedly; always be prepared.
  • First impressions can lead to significant investments.