The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: The Job of the CEO is Do As Little As Possible; How To Hire, What Questions To Ask, Why Pointy People are Always 100xers, How To Tell Great Stories Today & How Leaders Must Determine What To Delegate vs What To Control with Ian Siegel, Co-Founder an

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May 20, 2022

Ian Siegel, co-founder and CEO of ZipRecruiter, shares his insights on successful startups from bootstrapping to IPO. He discusses the importance of storytelling in tech, highlighting how great narratives can enhance product marketing. Siegel believes that a CEO's role is to manage effectively by doing less and empowering their team. He emphasizes hiring specialists over generalists and the significance of emotional intelligence in leadership. Tune in for his views on innovation and creating a supportive organizational culture.

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ANECDOTE

From Hollywood to Tech

Ian Siegel initially pursued writing, working for a Hollywood production company.
Disillusioned by the experience, he transitioned into tech, where his storytelling skills proved valuable.

INSIGHT

Storytelling's Importance

Storytelling is crucial for entrepreneurs, leaders, and effective communication.
It helps ensure clear understanding and allows for explanation to a layperson.

ADVICE

Empathetic Product Storytelling

When describing product features, focus on user stories and impact.
Illustrate how features improve user experience rather than just listing functionalities.

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Ian Siegel is the Founder and CEO @ ZipRecruiter, a leading online employment marketplace that uses AI-driven matching technology to actively connect millions of businesses and job seekers to their next great opportunity. Since co-founding the company in 2010, more than 1.8M employers have used ZipRecruiter to find their next great hire and over 500 million job applications have been submitted through the site. Prior to their IPO last year, Ian bootstrapped the company for many years to many millions in revenue before taking venture funding from IVP, Wellington Management and Basepoint Ventures to name a few. Before founding ZipRecruiter, Ian served in key leadership roles at CitySearch, Stamps.com, and Rent.com (an eBay company).

In Today’s Episode with Ian Siegel You Will Learn:

1.) The Founding of Olo:

How did Ian co-found ZipRecruiter from his kitchen with no venture funding and his 3 friends?
Why did they decide to not raise venture funding in the early days?
What was the catalyst at $50M in revenue for realising now was the right time to raise funding?

2.) The Art of Great Storytelling

What does truly great storytelling mean to Ian? What are the components of a great story?
Why do so many people today f*** up their product marketing and messaging?
Why does Ian believe Version 1.0 is the only one that takes true courage?

3.) CEO's Do As Little As Possible

Why does Ian believe his job as CEO is to do as little as possible?
How does Ian determine between the things he, the CEO should do, vs those those he should delegate?
Why does Ian believe the art of leadership and the art of parenting are the same?

4.) The Art of Hiring:

How has Ian's approach to hiring changed over the years?
What does Ian mean when he says, "I look for pointy people"? How does he detect them?
What are the two qualities that make the best execs? What questions reveal them?

5.) Parenting and Marriage:

Does Ian worry that with increasing family commitments, he loses an inch on work?
Why does he believe he is in an advantage as a CEO to those that do not have children?
What was the biggest argument he has had with his wife? How did it change his perspective?

Item’s Mentioned In Today’s Episode with Ian Siegel

Ian’s Favourite Book: Living with a SEAL: 31 Days Training with the Toughest Man on the Planet