
Rewind.ai & Optimizely CEO & Founder, Dan Siroker, on augmenting human memory with AI, building Optimizely, AI in operations, privacy and security, hiring and building extraordinary teams, and AI's impact on STEM education
12/05/23 • 58 min
(05:11 - 05:38) Memory and the Evolving Digital Age
(06:56 - 08:05) Tech and Memory Retrieval
(11:40 - 12:51) Chat GPT and Data Privacy Integration
(17:34 - 18:44) Leveraging AI for Company Augmentation
(22:34 - 23:47) AI for Efficiency and Exceptional Hiring
(30:31 - 31:01) Pivoting to Capture Meeting Data
(38:38 - 39:00) COO and Chief of Staff Collaboration
(43:27 - 44:27) Using Cultural Values as a Guide
(47:10 - 48:20) Accountability and Candor in Successful Teams
(55:58 - 57:01) Impressions of AI Summarization
---
(00:11) Augmenting Human Memory With AI
This chapter of Between Two COOs features a conversation with Dan Sroker, co-founder and CEO of Rewind, a personalized AI tool that augments human memory. Host Michael Kanag explores the inspiration behind Rewind and how it can give users a "superpower" by making all their digital interactions searchable and AI-able. They also discuss the importance of memory and how technology can enhance our natural capabilities. The conversation touches on the potential impact of relying on AI for memory recall and draws parallels to the evolution of phone numbers. Overall, this chapter explores the fascinating intersection of technology and human memory.
(12:51) The Future of AI in Operations
This chapter explores the potential impact of AI on future operations. Our guest, who has experience in scaling a company using AI, discusses how AI can be a powerful tool for leveraging human capabilities and increasing productivity. We also touch on the importance of privacy and security in AI, highlighting how companies that do not embrace it may struggle to compete in the future. The conversation concludes with a discussion on the role of AI in remote work and the potential for smaller teams to achieve more with the help of technology.
(18:44) Enhancing Productivity With Artificial Intelligence
This chapter explores the impact of AI on workplace productivity and efficiency. We discuss the release of GPT-4 and its potential to speed up tasks and increase productivity. Privacy challenges and the importance of employee awareness are also addressed. We examine how AI can bridge the gap between ambiguity and tasks, using Rewind's email summarization feature as an example. The significance of hiring exceptional senior staff and maintaining focus to achieve more with less is emphasized. Lastly, we touch on the potential impact of AI on the job market for recent graduates.
(27:19) The Impact of STEM on Technology
This chapter emphasizes the significance of STEM education in fostering creativity and problem-solving skills through technology. Our guest shares their personal journey with robotics, which led to the creation of innovative products like Optimize-A and Mac. The discussion also highlights the role of M1 and M2 chips in their company's pivot and how it enables local data privacy. Ultimately, we are reminded of the transformative potential of technology and the importance of adapting and maximizing its benefits.
(38:29) COOs and Chiefs of Staff
This chapter explores the dynamics of having a COO and chief of staff simultaneously, and how this partnership can benefit a company. We discuss the importance of screening for a good COO and chief of staff, as well as their role in creating a positive work environment. The former CEO shares his experience of achieving the number one spot for best place to work and the role of psychological safety in creating a fantastic workplace. Overall, this chapter provides valuable insights into the importance of a strong partnership between a CEO and their COO and chief of staff, and how it can contribute to the success of a company.
(42:23) Cultural Values in a Company
This chapter emphasizes the importance of defining and living up to company values. The host, who has experience at Google and now runs his own company, shares insights on creating a strong company culture by clearly defining values and behaviors that align with them. He highlights the need for these values to be a living document, constantly evolving and being used as a basis for performance management. The conversation also touches on the potential pitfalls of using values as a marketing tactic rather than a genuine reflection of the company's beliefs. Overall, this chapter highlights the role of company values in creating a positive and successful work environment.
(45:58) Psychological Safety in Leadership Importance
This chapter explores the importance of psychological safety in creating a successful and cohesive team. We discuss the guest's experience with psychological safety in their previous company and how they are implementing it in their current venture. We emphasize the need for a shared language and vernacular around psychological safety to create a sense of safety within a team. The guest also shares t...
(05:11 - 05:38) Memory and the Evolving Digital Age
(06:56 - 08:05) Tech and Memory Retrieval
(11:40 - 12:51) Chat GPT and Data Privacy Integration
(17:34 - 18:44) Leveraging AI for Company Augmentation
(22:34 - 23:47) AI for Efficiency and Exceptional Hiring
(30:31 - 31:01) Pivoting to Capture Meeting Data
(38:38 - 39:00) COO and Chief of Staff Collaboration
(43:27 - 44:27) Using Cultural Values as a Guide
(47:10 - 48:20) Accountability and Candor in Successful Teams
(55:58 - 57:01) Impressions of AI Summarization
---
(00:11) Augmenting Human Memory With AI
This chapter of Between Two COOs features a conversation with Dan Sroker, co-founder and CEO of Rewind, a personalized AI tool that augments human memory. Host Michael Kanag explores the inspiration behind Rewind and how it can give users a "superpower" by making all their digital interactions searchable and AI-able. They also discuss the importance of memory and how technology can enhance our natural capabilities. The conversation touches on the potential impact of relying on AI for memory recall and draws parallels to the evolution of phone numbers. Overall, this chapter explores the fascinating intersection of technology and human memory.
(12:51) The Future of AI in Operations
This chapter explores the potential impact of AI on future operations. Our guest, who has experience in scaling a company using AI, discusses how AI can be a powerful tool for leveraging human capabilities and increasing productivity. We also touch on the importance of privacy and security in AI, highlighting how companies that do not embrace it may struggle to compete in the future. The conversation concludes with a discussion on the role of AI in remote work and the potential for smaller teams to achieve more with the help of technology.
(18:44) Enhancing Productivity With Artificial Intelligence
This chapter explores the impact of AI on workplace productivity and efficiency. We discuss the release of GPT-4 and its potential to speed up tasks and increase productivity. Privacy challenges and the importance of employee awareness are also addressed. We examine how AI can bridge the gap between ambiguity and tasks, using Rewind's email summarization feature as an example. The significance of hiring exceptional senior staff and maintaining focus to achieve more with less is emphasized. Lastly, we touch on the potential impact of AI on the job market for recent graduates.
(27:19) The Impact of STEM on Technology
This chapter emphasizes the significance of STEM education in fostering creativity and problem-solving skills through technology. Our guest shares their personal journey with robotics, which led to the creation of innovative products like Optimize-A and Mac. The discussion also highlights the role of M1 and M2 chips in their company's pivot and how it enables local data privacy. Ultimately, we are reminded of the transformative potential of technology and the importance of adapting and maximizing its benefits.
(38:29) COOs and Chiefs of Staff
This chapter explores the dynamics of having a COO and chief of staff simultaneously, and how this partnership can benefit a company. We discuss the importance of screening for a good COO and chief of staff, as well as their role in creating a positive work environment. The former CEO shares his experience of achieving the number one spot for best place to work and the role of psychological safety in creating a fantastic workplace. Overall, this chapter provides valuable insights into the importance of a strong partnership between a CEO and their COO and chief of staff, and how it can contribute to the success of a company.
(42:23) Cultural Values in a Company
This chapter emphasizes the importance of defining and living up to company values. The host, who has experience at Google and now runs his own company, shares insights on creating a strong company culture by clearly defining values and behaviors that align with them. He highlights the need for these values to be a living document, constantly evolving and being used as a basis for performance management. The conversation also touches on the potential pitfalls of using values as a marketing tactic rather than a genuine reflection of the company's beliefs. Overall, this chapter highlights the role of company values in creating a positive and successful work environment.
(45:58) Psychological Safety in Leadership Importance
This chapter explores the importance of psychological safety in creating a successful and cohesive team. We discuss the guest's experience with psychological safety in their previous company and how they are implementing it in their current venture. We emphasize the need for a shared language and vernacular around psychological safety to create a sense of safety within a team. The guest also shares t...
Previous Episode

Arcadia COO, Kate Hennigsen, on Clean Tech and Disrupting the Energy Market, Non-Traditional Backgrounds for Working in Tech (and Ops!), Energy Regulation, M&A, Board, Risk, and Cash Management, & the Power of a Well Written Cold Email
(00:12) Clean Tech and Disrupting Energy Market
(06:15) Community Solar and Renewable Energy Innovation
(15:37) Data Platform and Energy Transformation
(24:21) Acquisitions, Integration, and Board Composition
(29:05) Startup Board Management and Risk Balancing
(35:51) Leadership, Growth Mindset, and Overcoming Challenges
(42:18) Connecting Through Cold Emails
(00:12) Clean Tech and Disrupting Energy Market
We discuss Energy 101 today with Kate Hemington, co-founder and COO of Arcadia Power. Kate has a degree from the University of Oxford and a background in corporate litigation, making her well-equipped to tackle the energy industry. We talk about energy being a regulated monopoly, the trillions of dollars in the market, and how Arcadia is bringing digitization opportunities. We also discuss the unique perspective of having a legal and policy background and how it allowed them to get into the market and innovate. Kieran and Kate bring their own experience with energy policy and law, respectively, to the conversation.
(06:15) Community Solar and Renewable Energy Innovation
We enter the complex world of community solar. She explains how the state incentivizes third party developers to build renewable power sources and how Arcadia simplifies the process by giving customers a guaranteed savings rate. We understand how electricity works and why community solar is a guaranteed win for the customer, as well as how it’s helping to displace dirty electrons with clean ones.
(15:37) Data Platform and Energy Transformation
We chat about the potential of retrofitting four billion machines to achieve maximum decarbonization. We explore how the market has shifted in the last 15 years, with over 90% of new electrons produced in the US being renewable. We also discuss how Arcadia's data platform, Arc, is providing other companies with data, such as EV manufacturers and solar developers, to help their customers with micro decisions. Finally, we consider how Arcadia is managing its mission and culture with its switch to serving enterprises.
(24:21) Acquisitions, Integration, and Board Composition
We discuss acquisitions and product integration. We explore the importance of growth and expansion, and how to know when an acquisition is right. We examine the challenges of integrating products, the risks of taking on too much too soon, and the importance of understanding a company and its culture before making an acquisition. We also look at the value of an independent board member, and the importance of having a plan when it comes to acquisitions.
(29:05) Startup Board Management and Risk Balancing
We explore risk management and cash management. Kate shares how they've become better at board management, and how to let board members know what you need from them. We discuss how macroeconomic events have led to a guard your flank mentality, but how regulated line of revenue has given them a floor. We also talk about how the energy transition is a larger market than the macroeconomic events and how it has helped them to be aggressive in a down environment. Finally, Kate shares her thoughts on tight times and how it has created a renewed focus.
(35:51) Leadership, Growth Mindset, and Overcoming Challenges
We explore the importance of understanding growth mindset and being comfortable with discomfort. We also look at the importance of communication in building a successful team and how to effectively manage people. Kate shares her experience of bringing a global operations team together and the challenges of leading a co-founder. Finally, we look at the moment of surprise when the team received five cease and desist letters from utilities and how they overcame the challenge.
(42:18) Connecting Through Cold Emails
The power of cold emails. We emphasize the importance of making connections, and provide advice on how to maximize reaching out to potential contacts. Tap into the power of cold emails and take the opportunity to make meaningful connections. Don't forget to subscribe to Between Two COOs and leave us a review on Apple Podcasts to share your thoughts and help spread the word.
Kate on LinkedIn: https://www.linkedin.com/in/kate-henningsen/
Episode: https://betweentwocoos.com/arcadia-power-coo-kate-hennigsen
Arcadia Power: https://www.arcadia.com/
Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514
Next Episode

Doist COO Allan Christensen on remote ops, perfecting hiring, designing ops for career development, the ideal employee feedback loop
(00:12) Interview With Remote COO Alan Christensen
COO Alan Christensen shares his journey and Duist's success without institutional investment, pioneering remote work and dividing responsibilities with CEO.
(11:48) Future of Remote Work and Communication
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(22:28) Recruitment, Career Growth, and Feedback Processes
Hiring, company culture, flat hierarchy, career development, and professional growth are emphasized by the speaker.
(31:04) Challenges With Trademarks and Feedback
Remote company Todoist's values, challenges, hands-on management, stable squads, feedback framework, and trademark infringement case.
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