Lessons from Esther Crawford

Esther Crawford, a prominent figure in the tech industry, has shared numerous insights and lessons from her dynamic career as an entrepreneur, product leader, and angel investor. From her early days as a startup founder to her high-profile role at Twitter during a tumultuous period, Crawford's journey offers a wealth of knowledge on work, leadership, and personal growth.

On Work Ethic and "Hustle Culture"

On intense work periods: "When your team is pushing round the clock to make deadlines sometimes you #SleepWhereYouWork."
- Source: Esther Crawford's Twitter (now X) post. While the original tweet is no longer available, it was widely reported. [1]
The rationale behind intense effort: "Doing hard things requires sacrifice (time, energy, etc). I have teammates around the world who are putting in the effort to bring something new to life so it's important to me to show up for them & keep the team unblocked."
- Source: A follow-up tweet from Esther Crawford, which is also no longer directly accessible but was cited in numerous articles. [2]
A reflection on hard work after being laid off: "The worst take you could have from watching me go all-in on Twitter 2.0 is that my optimism or hard work was a mistake."
- Source: Esther Crawford's Twitter (now X) post.
On being in the "arena": "Those who jeer & mock are necessarily on the sidelines and not in the arena. I'm deeply proud of the team for building through so much noise & chaos."
- Source: Esther Crawford's Twitter (now X) post.
On the necessity of difficult periods: "I don't regret putting in long hours or being ambitious and feel proud of how far I've come from where I started thanks in part to that type of work ethic."
- Source: YouTube video of Esther Crawford reading her blog post.
Viewing challenges as a game: "I think of life as a game and being at Twitter after the acquisition was like playing life at level 10 on a hard mode."
- Source: YouTube video of Esther Crawford reading her blog post.

On Entrepreneurship and Startups

On the reality of startup life: "When an acquisition announcement like this is made it often reads like an overnight success, so I'd like to take a minute to disavow readers of that very flattering but incorrect idea."
- Source: Esther Crawford's Medium article on Squad's acquisition.
On finding her voice as a CEO: "It took time for me to find my voice and confidence — but day by day, it happened."
- Source: Esther Crawford's Medium article on Squad's acquisition.
The power of pivoting: "Our product wasn't working and so we decided to give ourselves a blank slate and a fresh start, which is when the idea for Squad arrived."
- Source: Esther Crawford's Medium article on Squad's acquisition.
On the acquisition process: "Being acquired by a big company is a whole thing. Honestly, I knew very little about the process just a few months ago and wouldn't have believed how many people it takes to get a deal like this done."
- Source: DocSend Blog. [3]
On choosing an acquirer: "We chose Twitter because we felt a strong alignment around culture-fit and what we could build together."
- Source: DocSend Blog. [3]
On the emotional journey of a founder: "Since this was my first time running a venture-backed company everything was new and I often struggled with imposter syndrome. I worried that I didn't pattern-match with other startup CEOs in the news and at times I let that fear and anxiety get the best of me."
- Source: Esther Crawford's Medium article on Squad's acquisition.
On the importance of self-honesty with investors: After realizing her initial product was ahead of its time, she had a difficult conversation with an investor. This honesty led to greater trust.
- Source: An article by Dr. Gena Gorlin on her conversation with Esther Crawford. [4]
On taking calculated risks: Despite being a single mother, she invested her own savings into her startup, knowing the worst-case scenario was getting a job.
- Source: An article by Dr. Gena Gorlin on her conversation with Esther Crawford. [4]
On the dangers of "stealth mode": She advocates for launching in public to get critical feedback faster.
- Source: "Finding Joy Every Day" podcast episode with Esther Crawford. [5]

On Leadership and Management

On supporting a team during layoffs: She advised against demonizing remaining employees, who often have to pick up more work.
- Source: ABP Live article on her tweets after being laid off.
On the nature of business relationships: "At the end of the day businesses are not families - they're teams."
- Source: ABP Live article on her tweets after being laid off.
On seizing opportunities during transitions: "If you're one of those people it's okay to shoot your shot. Leaders are made in these moments."
- Source: ABP Live article on her tweets after being laid off.
On her leadership style at Twitter: "I didn't do it for praise. I did it because I believed in the team and the mission."
- Source: The Bulletin Time. [6]
On the importance of empathy in product development: "Products that facilitate human connection and communication require a different type of social-emotional intelligence."
- Source: YouTube video of Esther Crawford reading her blog post.
On navigating bureaucracy: "You couldn't just be a builder you also needed to be a politician."
- Source: YouTube video of Esther Crawford reading her blog post.

On Technology and Its Impact

On the mission behind her startup, Squad: "We wanted to make tech more human."
- Source: The Bulletin Time. [6]
On joining Meta: "I am obsessed with how humans connect through technology - and no other company has a bigger scale of impact in that space than Meta, which connects nearly 4B people (half of humanity)."
- Source: NDTV article on her joining Meta.
On the future of messaging: "Messaging has transformed how we connect with friends, family, creators, businesses, and now even AI."
- Source: NDTV article on her joining Meta.
On the potential of technology to solve loneliness: "We saw the problem of loneliness and wanted to use technology to help solve it."
- Source: Esther Crawford's Medium article on Squad's acquisition.
On the evolution of social media: "Consumer social is very much alive and at a fascinating juncture."
- Source: YouTube video of Esther Crawford reading her blog post.
On the cost of innovation for startups: "Weird seeing people who are supposedly champions of startups and Little Tech cheer on the introduction of a $100k for H-1Bs given it'll immediately be cost prohibitive for early-stage startups to hire from that very talented pool. Big Tech can absorb the fees, startups can't."
- Source: Techmeme. [7][8]

On Personal Growth and Philosophy

Her life motto: Her Medium bio reads, "Life story: 'Nevertheless, she persisted.'"
- Source: Esther Crawford's Medium Profile.
On following curiosity: "At every step along the way, I just followed what I was really deeply curious about."
- Source: "She's Got Moxie" podcast episode with Esther Crawford. [1]
On her early career aspirations: "I didn't grow up thinking I'd be in tech. I just followed what interested me."
- Source: The Bulletin Time. [6]
On dealing with layoffs: "For those laid off, it can be jarring to suddenly have a piece of your identity taken away — especially if you were truly passionate about the problem & work."
- Source: ABP Live article on her tweets after being laid off.
On financial literacy: "I started to realize that they thought of money so differently than I did. They thought of it as an asset that could go work for them; I just thought of it as something you earn in order to buy the things you want. Those are completely different world views."
- Source: Frec blog. [3]
On building generational wealth: "How can I leverage the money that I'm earning to provide experiences for my family, and also have that money grow?"
- Source: Frec blog. [3]
On her background: "I grew up on welfare, with a single mom. So I didn't really have a lot of models for financial literacy."
- Source: Frec blog. [3]
On her personal interests: "On weekends you'll likely find me hiking, tinkering with new apps, or hanging out with my family."
- Source: Esther Crawford's Personal Website. [9]
On being a role model: Her success shows that women can achieve great things in the tech industry, regardless of their age or gender.
- Source: JazzyDeals. [10]
On her personal brand: "I'm a product builder and angel investor."
- Source: Esther Crawford's Personal Website. [9]

On Elon Musk and Twitter 2.0

A nuanced view of Elon Musk: "Elon doesn't deserve to be venerated or vilified. He's a complicated person with an unfathomable amount of financial and geopolitical power."
- Source: YouTube video of Esther Crawford reading her blog post.
On Musk's strengths and weaknesses: "His boldness, passion and storytelling is inspiring, but his lack of process and empathy is painful."
- Source: YouTube video of Esther Crawford reading her blog post.
On Musk's talent: "Elon has an exceptional talent for tackling hard physics-based problems but products that facilitate human connection and communication require a different type of social-emotional intelligence."
- Source: YouTube video of Esther Crawford reading her blog post.
On the potential of X (formerly Twitter): "I disagree with many of his decisions and am surprised by his willingness to burn so much down, but with enough money and time, something new & innovative may emerge."
- Source: YouTube video of Esther Crawford reading her blog post.
On the internal state of pre-acquisition Twitter: "Twitter often felt siloed and bureaucratic... you couldn't just be a builder you also needed to be a politician."
- Source: YouTube video of Esther Crawford reading her blog post.
On her initial optimism about the acquisition: "I was cautiously optimistic. I saw him as the guy who built incredible and enduring companies like Tesla and SpaceX."
- Source: YouTube video of Esther Crawford reading her blog post.
On the unpredictability of working with Musk: She has opened up about it being difficult to work under him due to his unpredictable nature.
- Source: The Washington Times.
On the decision for mass layoffs: She supported the decision, stating, "Drastic cuts were going to be required to survive, no matter who owned the company."
- Source: FirstCuriosity. [1]

On Investing and Finance

Her approach to personal investing: She puts most of her money in index funds "because I have the belief that there's no individual who can reliably beat the market."
- Source: Frec blog. [3]
On managing her own money: "I hated that so many advisors and services were going to take a big percentage of my money. And there's so much great technology out there for automating this stuff."
- Source: Frec blog. [3]
As an angel investor: "Now, she writes $25k angel checks as a scout for Sequoia."
- Source: Frec blog. [3]
On trusting a new financial service: As an entrepreneur, she knew the most important thing was to look into the team.
- Source: Frec blog. [3]
On the value of tax-loss harvesting: "As I learned more about it, I realized it could be really useful for me down the road."
- Source: Frec blog. [3]

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