20VC The Story of Ring Scaling from an Idea in a Garage to Richard Branson Investing and a Reported $1BN Amazon Acquisition Why Building a Brand is Like Making Great Wine The Secret to Hiring Success; Hire Marathoners and more with Jamie Siminoff

In this insightful conversation, Jamie Siminoff, the founder of Ring, shares his journey from tinkering in his garage to creating a globally recognized brand that Amazon acquired for $1 billion. Siminoff candidly discusses the highs and lows of entrepreneurship, including taking massive inventory risks and facing near-bankruptcy moments before Amazon's acquisition. He emphasizes the importance of mission-driven entrepreneurship, revealing how Ring's aim to enhance neighborhood safety drove its innovation and success. As he prepares to step down as CEO to focus on his role as Chief Inventor, Siminoff reflects on the lessons learned from Amazon, the impact of parenting on risk-taking, and his hopes for the future. Alongside the personal narrative, the episode also features discussions on Ironclad's contract management platform and Harvard Management Company's investment philosophy, highlighting the importance of innovation and partnership in the venture landscape.

• Entrepreneurship often involves a level of reality distortion, requiring belief in seemingly unattainable goals.
• Jamie Siminoff had to take the risk of ordering $500 million of inventory when Ring was only a $100 million business.
• Ring broke a sales record on QVC with $22.6 million in sales in a single day.
• Siminoff communicated to investors and Amazon that he was prepared to either go public or sell to Amazon.

"A lot of entrepreneurship is like reality distortion. You have to believe in something that's much bigger and crazier than what can actually be accomplished."

This quote emphasizes the need for entrepreneurs to have an almost unrealistic belief in their vision in order to take the necessary risks to succeed.

• Great entrepreneurship is characterized by identifying a problem and creating a solution that addresses a genuine consumer need.
• Jamie Siminoff exemplifies this by developing the world's first Wi-Fi video doorbell, Ring, which scaled from a garage project to a global brand.
• Amazon acquired Ring in 2018 for a reported $1 billion.

"So what is truly great entrepreneurship? Well, to me, it's finding a problem and creating an incredible solution that solves that real consumer problem."

Harry Stebbings offers his perspective on what constitutes truly great entrepreneurship, highlighting the importance of problem-solving and consumer value.

• Ironclad provides a leading contract lifecycle management platform that streamlines contracting processes for modern businesses.
• The platform is designed to be user-friendly and supports various types of contracts, utilizing AI and workflow capabilities.
• Ironclad's clients include major companies like L'Oreal and Mastercard.

"It's 2023. We need contracts to keep pace with the speed of modern business. And that's where ironclad comes in."

This quote underlines the necessity for businesses to have efficient contract management solutions that align with the fast-paced nature of modern commerce.

• Harvard Management Company (HMC) manages Harvard University's endowment and has a history of venture capital investment.
• HMC provides support and insight to help managers and entrepreneurs succeed.
• They are open to partnering with both new and established fund managers.

"Harvard Management Company is constantly seeking out the next generation of great investors and entrepreneurs."

The quote reflects HMC's commitment to identifying and nurturing investment opportunities and entrepreneurial talent.

• Jamie Siminoff's "aha moment" for Ring was not instantaneous but rather a gradual realization.
• The concept for Ring came from a personal need when Siminoff could not hear his doorbell and hacked together a solution.
• The idea gained traction when his wife expressed that the makeshift Wi-Fi doorbell made her feel safer.

"It was an iterative aha. It wasn't just like a, wow, I invented this."

Siminoff describes the development of Ring as a series of small realizations rather than a single, defining moment of invention.

• Siminoff's drive to help people and solve problems stems from his childhood experiences.
• Learning to focus his energy on solving specific problems was a key lesson for him as an entrepreneur.

"The hardest thing I had to learn was you can't solve every problem for everyone because then you do nothing like how to focus."

This quote highlights the importance of focus and prioritization in successful problem-solving and entrepreneurship.

• Siminoff acknowledges a desire for recognition and the satisfaction that comes from others acknowledging his success.
• The discussion touches on the human aspect of entrepreneurship, where personal history can influence one's drive for approval and success.

"I always say I don't have an ego, but I certainly like people seeing me successful."

Siminoff admits to enjoying recognition for his achievements, suggesting that personal validation can be a motivating factor for entrepreneurs.

• Richard Branson's investment in Ring came about through a series of connections and a demonstration of the product's impact on neighborhood safety.
• Branson's endorsement provided credibility and significantly boosted Ring's brand.
• The story illustrates the importance of networking, mission alignment, and leverage of influential investments.

"Richard Branson doing a blog post saying, I invested in this because it makes neighborhoods safer and I'm a missionary investor."

The quote demonstrates how a high-profile investor like Branson can amplify a company's mission and contribute to its growth narrative.

• High-profile investors can offer credibility and contribute to a company's success, but they are not a guarantee for customer acquisition.
• Strategic use of such investments as part of a broader marketing and brand-building strategy is essential.

"That credibility of Richard saying that really turned the whole thing."

Siminoff emphasizes the transformative impact that Richard Branson's investment and public support had on Ring's credibility and brand perception.

• Siminoff criticizes the search for a "silver bullet" in entrepreneurship, emphasizing the need for hard work and dedication.
• He values individuals who are deeply committed to their vision and willing to put in the effort required to achieve it.

"It's dirt under your fingernails. I want the people that are missionary passionate dirt under the fingernails and realize how hard this is going to be."

This quote captures the gritty reality of entrepreneurship, where passion and perseverance are crucial for overcoming challenges.

• Siminoff looks for individuals who are relentless in their pursuit of their goals, akin to marathon runners who train and compete for personal accomplishment.
• Determination and self-motivation are key traits he seeks in potential hires and team members.

"They have to do this. I always say we want marathoners at ring."

Siminoff uses the metaphor of marathon runners to describe the type of dedicated and self-driven individuals he believes are necessary for success in entrepreneurship.

• Ring faced several near-bankruptcy situations, including a pulled $100 million investment round and a lawsuit that led to an injunction against their product.
• The company's rapid growth and the associated risks were significant challenges that required careful navigation.

"We had four or five real run out of money kind of times."

Siminoff recounts the precarious financial situations that Ring endured, highlighting the volatility and risk inherent in growing a startup.## Financial Struggles and Team Resilience

• Jamie Siminoff's company experienced a significant financial crisis, going negative by $50 to $70 million.
• Jamie becomes calm in extreme situations, likening his demeanor to that of a pilot in an emergency.
• He informed the factories of their financial situation and negotiated continued product shipment.
• Jamie was transparent with his team about the company's dire financial state.
• The team unified and worked together to sell their entire inventory during the holiday season.
• Their efforts resulted in breaking a QVC sales record with $22.6 million in a single day.
• Shortly after overcoming this crisis, Ring signed a term sheet with Amazon.

"So we probably went negative 50 to 70 million at one point. But that's just because we just didn't pay the factories."

This quote highlights the depth of the financial crisis faced by Jamie's company, where they were significantly in debt due to unpaid bills to their factories.

"We got to sell this holiday. We'd do everything we can to sell everything we can this holiday."

Jamie's strategic approach to resolving the financial crisis was to maximize sales during the critical holiday period, rallying his team to focus on this goal.

"We broke the record for QVC for the year, for sales in a day. $22.6 million in a day."

The result of the team's efforts is encapsulated in this quote, showing their remarkable achievement of record-breaking sales in a single day.

• Jamie Siminoff discusses the unique challenges faced during different phases of company growth, from a small team to a larger organization.
• He explains that smaller mistakes were manageable in early stages, but as the company grew, the problems and their impacts became larger.
• The transition from 30 to 170 employees was particularly challenging, with less personal problem-solving and a reduced safety net from investors.
• As the company scaled further, investors were unable to provide the same level of financial support during crises.

"30 to 170, you're sort of in there and you can get people to back you. 170 to 500, they took away the. You're on the tightrope and all of a sudden you look down and they're pulling the mats away."

Jamie reflects on the increasing difficulty of scaling, metaphorically describing the removal of safety nets as the company grew larger.

• Jamie Siminoff believes that a brand must immediately communicate its core value to customers.
• He emphasizes the importance of authenticity in building a brand and how every aspect of the company should align with its North Star.
• Jamie kept his email on every product box to maintain direct communication with customers, which scaled well and kept the team accountable.
• He criticizes the use of surveys, advocating for listening to "ground truth" from customers to guide product development and company growth.

"When you walk into a store and you see our logo, you have to feel immediately, I know that whatever's in that box is going to make my neighborhood safer."

This quote captures Jamie's definition of a strong brand, one that conveys trust and purpose at first glance.

"I think iconic brands come initially from authenticity though too."

Jamie stresses that authenticity is the foundation of an iconic brand, suggesting that genuine values resonate with customers and team members.

• Jamie highlights the importance of listening to customers rather than relying on surveys.
• He shares how customer feedback led to the development of new products like the car camera and an indoor flying camera drone.
• The company's mission to make neighborhoods safer guides product development, ensuring alignment with their core values.

"Listen to your fucking customers."

Jamie's blunt advice underscores the importance of direct customer engagement for understanding their needs and improving products.

"Our mission is to make neighborhoods safer. Now you have a mission. Everyone's focused on it."

The mission statement serves as a guiding principle for product development decisions, ensuring that new products align with the company's goals.

• Jamie discusses the daunting experience of competing with established companies like Google.
• He describes the company's aggressive approach to competition, aiming to be memorable even in failure.
• Jamie values a strong mission over financial metrics when considering investments and partnerships.

"We're not going to squeak our way out of business. We are going to literally be the greatest bankruptcy of all time."

This quote illustrates Jamie's all-or-nothing attitude towards competition and the pursuit of the company's mission.

"Business changes, technology changes, chatbot AI comes out. What do you want in your soul to achieve?"

Jamie emphasizes the importance of a founder's intrinsic motivation and mission, which he believes should be central to any business endeavor.

• Jamie compares building a company to making wine, suggesting that stress leads to innovation and quality.
• He agrees with the idea that CEOs should insert risk into the business, but prefers to think of it as imposing constraints to foster creativity and progress.

"The stress of the problems we had led to the innovations."

Jamie attributes the company's innovation to the challenges they faced, implying that overcoming adversity is essential to success.

"You have to keep putting yourself in the box."

He advocates for setting ambitious goals and constraints to push the company towards continuous improvement and innovation.## Balancing Personal and Business Constraints

• Jamie Siminoff acknowledges the challenge of balancing time and effort between business and personal life.
• He emphasizes the importance of not overextending in either area, using the metaphor of grape cultivation to illustrate the need for balance.
• Jamie suggests that without proper care, both personal and professional ventures can fail, much like grapes needing water and fertilizer to produce wine.

"I always realize I'm always pushing myself deeper, whether it's my time into something. So it is learning how to balance those constraints and whether the business or personal, so that they don't go too far."

The quote highlights Jamie's self-awareness regarding his tendency to immerse himself deeply in his commitments and the importance of managing this to avoid negative consequences.

• Jamie details the background of Ring's acquisition by Amazon, emphasizing the importance of a forged relationship and mutual cultural understanding.
• He shares the anecdote of the moment when the acquisition was proposed, describing it as a "Zoolander moment" due to initial confusion.
• Jamie explains his choice of Amazon for acquisition, stating his belief that Amazon would honor Ring's mission and allow the company to continue executing on it.

"Amazon had been obviously a lot of stuff in the home... And so they came to us to integrate with the Alexa with the screen... It was a great run of doing that. And that's what led to then in the end, that's where they said, let's put this together."

This quote explains how Ring's prior relationship with Amazon and the integration with Alexa led to the acquisition offer.

• Jamie Siminoff discusses facing potential failure, describing his methodical approach to overcoming challenges.
• He shares his personal experience of almost losing Ring and how the fear of failure has driven him to focus and persevere.
• Jamie reveals the emotional toll of these experiences, suggesting that he may still be dealing with the stress and potential PTSD.

"I take all the stress of it... but I push it all to the side, and there's only one road to live, and I got to go down that road, and it's risky, but I'm going to do it because if you flail, you're dead."

This quote captures Jamie's strategy for dealing with extreme stress by compartmentalizing and focusing on the necessary actions to survive a crisis.

• Jamie discusses how he celebrated the Amazon acquisition, including buying a mountain bike and other unnamed items.
• He describes the surreal experience of seeing the transaction funds appear in his account and how he shared the moment during a speaking engagement.
• Jamie admits that the financial security from the deal did not diminish his passion for Ring's mission.

"So it just happens that I'm literally there and the money is supposed to come in, and I'm literally sitting there, I'm speaking, and I just hit like, a refresh, and all of a sudden I'm like, holy shit."

This quote conveys the real-time excitement and disbelief Jamie experienced when the acquisition funds finally arrived in his account.

• Jamie Siminoff talks about the role of fear in his entrepreneurial journey, describing it as a driving force rather than a paralyzing one.
• He contrasts his fear-driven motivation with a famous quarterback's confidence, highlighting that success can come from different mindsets.
• Jamie's fear has led him to overcompensate in areas like branding and customer service, ensuring that he does everything possible to succeed.

"I'm so in fear of everything that I overcompensate on the other side... It's the fear that drives me for that, which is a funny thing, because you think it's confidence."

The quote reveals Jamie's introspection on how fear, rather than confidence, has been the catalyst for his actions and success.

• Jamie attributes the successful integration of Ring into Amazon to a mutual cultural fit and his own commitment to being "all in" on Amazon.
• He emphasizes the importance of authenticity and earning trust, both internally and with Amazon, to ensure a smooth transition.
• Jamie praises Amazon's respect for Ring and their hands-off approach, allowing natural integration over time.

"The first email I got the day it closed came from Jeff and said, don't let us mess it up, you are in control."

This quote illustrates the level of autonomy and trust that Amazon provided to Jamie and Ring, setting the tone for a successful post-acquisition relationship.

• Jamie discusses the importance of trust in building a team and his willingness to take risks on people, despite past experiences of broken trust.
• He argues that experiencing betrayal should not prevent one from trusting again, as the benefits of finding trustworthy individuals outweigh the risks.
• Jamie advises that when trust is broken, the appropriate response is to remove the untrustworthy individual rather than becoming more guarded.

"I'm always willing to take another risk because you have to earn trust, you have to take risk."

The quote underscores Jamie's philosophy that trust is essential and worth the inherent risk involved in building a team.

• Jamie reflects on the role of emotions in leadership, acknowledging that while they can sometimes be counterproductive, they can also be a powerful motivator.
• He admits to learning from past experiences where uncontrolled emotions were detrimental, but also recognizes the authenticity and passion they can convey to a team.
• Jamie suggests that showing genuine care and concern for the company's mission can inspire others to share in that passion.

"But over time, I've gotten better at letting the emotions help drive things... And then I think it does help drive things."

This quote indicates Jamie's belief that emotions, when managed properly, can positively influence leadership and team motivation.

• Jamie announces his decision to step aside as CEO of Ring and move into the role of chief inventor.
• He discusses the timing of this transition and his continued commitment to Ring's success, as well as his anticipation of having more time for other endeavors.
• Jamie hints at the influence of Amazon's culture in his decision, suggesting that the transition is part of the company's evolution.

"So the news is that I'm going to step aside as CEO of Ring and I'll be the chief inventor, which is what I always called myself."

The quote announces Jamie's shift in role at Ring and reflects his ongoing dedication to the company's innovation and mission.## Transition of Leadership at Ring

• Jamie Siminoff acknowledges that Ring has grown significantly and requires a new CEO.
• He expresses his desire to remain involved with product development and customer engagement.
• The transition process began a year ago with the support of Dave Limp from Amazon.
• Jamie views Ring as his "child" and is deeply attached to its success and future.

"I talked to Amazon a year ago and I said, I think where my passion is where I am, I think I'm a good business leader, but this thing's gotten so big that there's probably a better person now."

Jamie Siminoff reflects on his conversation with Amazon, indicating his self-awareness about his role and the need for a new leader due to the company's growth.

• Jamie jokes about Ring's financial success in comparison to his affection for his son, Oliver.
• He emphasizes the importance of integrating his son into his life and business journey.
• Jamie hopes his son finds his own passion, regardless of the financial freedom he may have.

"Ring is my child, it always will be. I'll always care for it, no matter what."

Jamie Siminoff equates his emotional investment in Ring to that of a parent for a child, illustrating his deep personal connection to the company.

• Jamie discusses the potential negative effects of growing up with wealth on finding happiness.
• He stresses the importance of instilling values in his son that focus on accomplishments and helping people, not on money.

"I think the money becomes a responsibility. I didn't have that. I was just able to go out and do my thing because I didn't have to worry about being who my dad was or whatever."

Jamie Siminoff explains his perspective on wealth and responsibility, indicating that not having the burden of family wealth allowed him to pursue his passions freely.

• The most difficult aspect of parenting for Jamie would be having a child who lacks empathy and kindness.
• He appreciates that his son has his own interests and passions, which differ from his own.

"The worst thing for me would be having an asshole as a kid."

Jamie Siminoff expresses his biggest fear as a parent, emphasizing the importance of raising a child who is empathetic and caring.

• Ring was started when Jamie's son was three, and his son was actively present in the early days of the company.
• The integration of family into the business is highlighted by the "Simonoff Brothers unite" anecdote.
• Jamie recognizes the influence of having a child on his drive and the consideration of risks.

"I started it when he was three in the garage."

Jamie Siminoff recounts the early days of Ring, highlighting the close connection between the growth of the company and his son's upbringing.

• Jamie describes his ability to switch off his work intensity and be present and relaxed with his family.
• He acknowledges that he has learned this balance over time and sees it as essential for a healthy personal life.

"I think something I've been lucky is to be somewhat balanced in and out."

Jamie Siminoff discusses his approach to maintaining a balance between his intense work ethic and his personal life, suggesting it is a learned skill.

• Jamie is uncompromising in his pursuit of excellence for Ring, emphasizing the importance of delivering 100% to customers.
• He shares his frustration with product timelines and his eagerness to release better versions.
• Jamie relates to Walt Disney's dissatisfaction at movie premieres, knowing improvements were on the horizon.

"Like, 100% is all that I will accept. I will not accept anything less."

Jamie Siminoff articulates his high standards and refusal to settle for mediocrity, demonstrating his commitment to customer satisfaction and product quality.

• Jamie recommends "Invention" by James Dyson as a must-read book.
• He expresses admiration for Dyson, indicating a personal influence on his own approach to invention and entrepreneurship.

"Oh, invention by James Dyson. Anything with James Dyson. I'm in. He's my man crush hero."

Jamie Siminoff identifies James Dyson as a significant influence and recommends his book, reflecting his respect for Dyson's work and innovation.

• Jamie discusses his evolving views on remote work and the balance between appreciating it and supporting Amazon's in-office policy.
• He contemplates the rapid scale and impact of Amazon, which has shifted his perspective from millions to billions.

"Amazon just went to basically a full in three days a week thing and I back them in that."

Jamie Siminoff shares his support for Amazon's policy on in-office work, while also acknowledging the benefits of remote work, indicating flexibility in his views.

• Jamie is excited about the current renaissance in technology and innovation, particularly in transportation and security.
• He remains optimistic about the world's future despite challenges and believes in the triumph of good over evil.

"I am very pro world, pro long term, pro excited."

Jamie Siminoff expresses a positive outlook on the future, focusing on the advancements and opportunities in various industries.

• Jamie has learned about operating at a massive scale through his experience with Amazon.
• He reflects on how this understanding of scale has changed his worldview and approach to business.

"I could never have imagined what scale and size is until I got into Amazon."

Jamie Siminoff comments on the eye-opening experience of understanding the vast scale of Amazon, which has influenced his perception of business operations.

• Jamie receives a manageable number of emails from customers due to Ring's organizational focus on customer satisfaction.
• He takes pride in being an effective communicator via email.

"Not that many. Like probably ten to 20 from neighbors."

Jamie Siminoff describes the volume of customer emails he receives, attributing the low number to the company's strong emphasis on customer satisfaction.

• Jamie finds the process of reducing the workforce to be a painful but necessary part of business.
• He reflects on the impact of these decisions on the team and the importance of doing the right thing for the company's health.

"One of the most painful things in the last year has been the reduction of force that's happened around our teams."

Jamie Siminoff shares his experience with the difficult decisions to reduce staff, emphasizing the emotional toll such actions can have on a team.

• Jamie criticizes the venture capital industry for overfunding and misdirecting entrepreneurs, leading to harmful outcomes.
• He calls for more discipline in venture capital to prevent negative impacts on entrepreneurs.

"It over watered the grapes and that was an unfair thing to do to entrepreneurs."

Jamie Siminoff critiques the venture capital industry for providing too much funding too quickly, which he believes can lead entrepreneurs astray and cause harm.

• Jamie hopes to continue as Amazon's chief inventor and to be involved in meaningful projects outside of Amazon.
• He desires to look back on five years of positive societal contributions and successful business ventures.

"I hope in five years we're able to see the things that I've done that have mattered and that I've continued to evolve in that way."

Jamie Siminoff shares his aspirations for the future, aiming to make a significant impact on society and continue evolving in his professional and personal endeavors.