The Onion’s Owner on Satire, Infowars, Defending Democracy & Trump
Last year, after pressure from activist investors, Jeff Lawson stepped down from his perch as CEO from Twilio, the cloud communications company he co-founded. But he didn’t spend any time twiddling his thumbs — that same spring, he bought the satirical news organization The Onion, and by the end of the year, they’d tried to buy Alex Jones’ Infowars at a bankruptcy auction.
Jeff also stayed busy on the political front, continuing his work on DemocracyFirst, a political action committee he co-founded, in 2022, to support candidates committed to democracy.
So there was plenty to chew on when Kara interviewed Jeff last week at Democracy’s Information Dilemma, a symposium hosted by the University of Michigan’s Gerald R. Ford School of Public Policy.
They discuss the tech founder mindset; how Jeff is remaking The Onion; why political satire is more necessary than ever; why DEI — which Jeff championed as a CEO — can sometimes do more harm than good; and how to fight for democracy during Trump 2.0.
Questions? Comments? Email us at on@voxmedia.com or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher.
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Twilio: Jeff Lawson
When Jeff Lawson co-founded Twilio in 2008, he had already been through a series of start-ups. Some succeeded, others fizzled out—but each provided insights that led him to build one of the most extensive communication platforms in business. Fueled by his frustration juggling customer calls while trying to run a surf and skate store in LA, Lawson realized he could use his coding skills and knowledge of cloud computing to help companies connect with customers. Twilio’s early communications technology quickly gained traction with developers at other start-ups like Uber, which used it to text riders that their car had arrived. Despite early skepticism from investors, Twilio eventually grew into a $4 billion business, with customers like Nike, Toyota, OpenAI, and Airbnb.
This episode was produced by Kira Wakeam, with music by Ramtin Arablouei
Edited by Neva Grant, with research help from Sam Paulson.
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Twilio CEO Jeff Lawson: the next $60B, Engage, Segment acquisition & more + Who actually uses Oculus? | E1308
It was great to have Jeff back on the pod! But first, Producer Rachel gives some updates on TWIST Founder Meetups (01:54) and Jason talks a bit about Oculus (14:12). Then, Jeff Lawson from Twilio joins (24:42) to discuss their new mission to build the leading customer engagement platform, the launch of their new product Twilio Engage, lessons from scaling & their big acquisitions, San Francisco and more!
20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jeff Lawson is the Founder & CEO @ Twilio, the company that allows you to unite communications and strengthen customer relationships across your business. Prior to their incredibly successful IPO in 2016 Jeff raised funding from some of the best including Bessemer, Union Square Ventures, Redpoint, Salesforce and Founders Fund to name a few. Before founding Twilio, Jeff was co-founder & CTO of NineStar, founding CTO of Stubhub.com, co-founder, CEO & CTO of Versity, and one of the first product managers for Amazon Web Services.
In Today's Episode with Jeff Lawson You Will Learn:
1.) How Jeff made his way into the world of tech and startups and what that founding a-ha moment was for Jeff with Twilio? When explaining new ideas to people, what signals to Jeff that the idea is resonating? Are there clear indicators an idea is not resonating?
2.) Leadership: What does great leadership mean to Jeff today? How has Jeff's leadership style changed and evolved over the years? What does Jeff believe is the key to great storytelling? How has the leadership style required, changed in a COVID world? What have been the biggest inflection points in his leadership?
3.) Culture: What does Jeff believe are the 3 key ingredients to company culture? How can leaders create a tribe that people associate with? What are the biggest lessons we can take from sport and religion when it comes to culture building? At what points has Jeff been concerned about the Twilio culture? What did he do to rectify it? Why are "values nice but principles better"?
4.) Decision-Making: How has Jeff created a culture of decentralised decision-making? What has Jeff done to ensure the best ideas rise to the top? In what ways can leaders ensure people feel safe to be bold and go big, without the fear of failure? How does Jeff determine when to give or remove resources from new ideas? How does Jeff think about the importance of "focus"?
5.) Diversity: Frank Slootman previously said, "diversity should not override merit". What are the core problems that Jeff has with this statement? How do Twilio construct their recruitment pipelines to ensure diversity? Why does Jeff believe the secret to human assessment is one of "miles travelled"? What are the signals of this?
Item's Mentioned In Today's Episode with Jeff Lawson
Jeff's Favourite Book: Made to Stick: Why some ideas take hold and others come unstuck
As always you can follow Harry and The Twenty Minute VC on Twitter here!
SaaStr 444: Twilio CEO, Jeff Lawson, and SaaStr CEO, Jason Lemkin, Host a Deeper Dive on How to Collaborate with Developers
Jeff Lawson, Twilio CEO and the author of "Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century," shares secrets on bridging the gap between your technical team and leadership team to maximize success.
This episode is an excerpt of Jason and Jeff's session from SaaStr Build. You can watch the full video here: https://youtu.be/WPvjG-44zJ4
SaaStr 419: How To Collaborate, Manage & Work with Developers with Jeff Lawson, CEO and Co-Founder @ Twilio and Jason Lemkin, CEO @ SaaStr
At his core, Jeff Lawson is a software developer first, and a CEO second. He knows both sides of the executive & engineering equation intimately. He gets what goes on in a developer's brain and the detailed process of building software, but he understands that businesses are motivated to move quickly. And in turn, developers need to adapt.
An all-time SaaStr fan-favorite, Jeff recently chatted with SaaStr CEO Jason Lemkin to discuss his thoughts on collaborating, managing, and working with developers.
Video and blog post: https://www.saastr.com/how-to-collaborate-manage-and-work-with-developers-featuring-jeff-lawson-twilio/
Jeff Lawson – How to Build a Platform - [Invest Like the Best, EP.158]
My guest this week is Jeff Lawson, the Founder, and CEO of Twilio. Twilio is a 15-billion-dollar company offering a cloud communications platform to its customers. Twilio is used by customers like Lyft, Twitch, and Yelp to make communications in their products easy. Jeff and I talk about why it pays to be a platform, how to be a platform, and how to sculpt a company culture. This is a must-listen for anyone building a business whether it’s a tech business or not.
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.
Follow Patrick on Twitter at @patrick_oshag
Show Notes
1:18 – (First Question) – Company vowels and draw the owl
5:26 – Significance of API’s
12:14 – How non-software businesses can transition into the space
17:50 - Agile way of working at ING Belgium (video)
18:38 – How they strategize their product build
23:27 – The idea of asking your developer and why it’s so important to them
33:02 – How they codified their business culture
45:12 – Parting advice for people building platforms
48:13 – Kindest thing anyone has done for Jeff
Learn More
For more episodes go to InvestorFieldGuide.com/podcast.
Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub
Follow Patrick on Twitter at @patrick_oshag
SaaStr 228: Twilio CEO Jeff Lawson and Glitch CEO Anil Dash on the Secrets to Building a Billion in ARR and Being an Ethical leader.
Join Glitch CEO Anil Dash and Twilio CEO Jeff Lawson for a discussion about the ethical implications of technology in today's society. Jeff and Anil discuss how social media and AI are changing the way we think about the impact of technology on society as well as the responsibility of tech leaders for this impact.
Missed the session? Here's what Jeff talks about:
How taking no stance as a business leader today, is taking a stance
How to set concrete numbers for diversity goals
The impact of corporate culture on employee happiness
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
SaaStr
Jeff Lawson
Anil Dash
SaaStr 218: Twilio Founder, Jeff Lawson & SendGrid CEO, Sameer Dholakia on Why Developer First Is A Maturation In The Supply Chain Of Software & Why With Software Innovation Costs Being Lower Than Ever, Operators Must Maximise The Number of "At Bat" Oppor
Jeff Lawson is the Founder & CEO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Jeff, prior to founding Twilio, Jeff was the Founder & CTO @ Nine Star Inc and enjoyed a spell at Amazon as a Technical Product Manager.
Sameer Dholakia is the CEO @ SendGrid, the category leader in email delivery, reaching half of the world's digital users every 3 months. Last year Twilio acquired SendGrid bringing email into one seamless customer engagement platform. As for Sameer, prior to joining SendGrid, he spent 4 years at Citrix, where he drove the company's product strategy for cloud infrastructure and server virtualization. Sameer joined the company in 2010, when Citrix acquired VMLogix, where he served as CEO and doubled revenues during each year of his tenure. Before that, he worked for 12 years at Trilogy, where he held key leadership roles helping the company grow from a start-up to a $300 million business.
In Today's Episode We Discuss:
How Jeff came to found Twilio and what was that a-ha moment for him? How did Sameer enter the world of SaaS and come to be CEO @ SendGrid?
How did Jeff and Sameer assess the culture fit between the 2 companies when deciding whether or not to join forces? How did they formulate and approach creating a new set of values with the 2 companies coming together? How do they distinguish between culture and values? How can leaders both be authoritative and vulnerable simultaneously?
What does Jeff mean when he says, "the developer first approach is a maturation of the supply chain of software"? How has Jeff seen his original thesis for "developer first" evolve and change with time? What does truly special customer experience look like in the developer first model?
In terms of product strategy, how do Jeff and Sameer approach when is the right time to release a second product? What does Jeff mean when he says, "you have to maximise the number of at bat opportunities you have"? Why does Sameer think that SendGrid waited too long to release additional product lines? What were his core learnings from that?
How do Jeff and Sameer think about what what truly special leadership looks like today? How do they approach speaking so that people will remember? What are some of their biggest tips to aspiring entrepreneurs with regards to that and team empowerment? Why do both Jeff and Sameer believe that so much of the management wisdom today is outdated?
60 Second SaaStr:
What do Jeff and Sameer know now that they wish they had known at the beginning?
The book they have gifted most often and why?
What does it take to truly be a great board member?
What do the next 5 years look like for Twilio? How big could it get?
Read the full transcript on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Jeff Lawson
Sameer Dholakia
a16z Podcast: What Software Developers (and Therefore Every Company) Need
The old constraint when it came to technology was hardware -- how many CPUs can I get my hands on. Today, spinning up compute can be done from any smartphone with an AWS account or something similar. The current constraint is software. And since software is written and operated by people, tackling that constraint comes down to making people as informed, enabled, and efficient as possible.
Three CEOs and co-founders of three companies that serve software developers -- Chris Wanstrath from GitHub, Jeff Lawson from Twilio, and Ben Uretsky of Digital Ocean -- take part in a conversation with a16z’s Peter Levine about the needs of software developers. What are the emerging platforms, ecosystems, and tools that help developers succeed at what is increasingly the most important job in any company – writing and running software.
The views expressed here are those of the individual AH Capital Management, L.L.C. (“a16z”) personnel quoted and are not the views of a16z or its affiliates. Certain information contained in here has been obtained from third-party sources, including from portfolio companies of funds managed by a16z. While taken from sources believed to be reliable, a16z has not independently verified such information and makes no representations about the enduring accuracy of the information or its appropriateness for a given situation.
This content is provided for informational purposes only, and should not be relied upon as legal, business, investment, or tax advice. You should consult your own advisers as to those matters. References to any securities or digital assets are for illustrative purposes only, and do not constitute an investment recommendation or offer to provide investment advisory services. Furthermore, this content is not directed at nor intended for use by any investors or prospective investors, and may not under any circumstances be relied upon when making a decision to invest in any fund managed by a16z. (An offering to invest in an a16z fund will be made only by the private placement memorandum, subscription agreement, and other relevant documentation of any such fund and should be read in their entirety.) Any investments or portfolio companies mentioned, referred to, or described are not representative of all investments in vehicles managed by a16z, and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. A list of investments made by funds managed by Andreessen Horowitz (excluding investments and certain publicly traded cryptocurrencies/ digital assets for which the issuer has not provided permission for a16z to disclose publicly) is available at https://a16z.com/investments/.
Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Please see https://a16z.com/disclosures for additional important information.
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