I failed 22 times... then I built a $2.5B Company

Christina's Journey and Early Career

• Christina has a company valued at $2.45 billion, but her journey to success was not immediate, and she had to overcome numerous failures along the way (59s).
• Christina had a good job, but she quit to try something new and make it on her own, which is a leap many people want to take but don't (1m27s).
• Before achieving success, Christina created 35 projects that went nowhere, and she views these failures as valuable learning experiences (1m42s).
• Christina initially had a job at USV, which she got by sending in links to her web presence, including her Twitter and Flickr profiles, as well as a design blog she had started a couple of months prior (2m15s).
• Christina lived in Berlin at the time, where she wanted to be a designer and started a design blog, which contributed to her getting hired by USV (2m45s).
• When leaving USV in 2012, Christina was advised to specialize in crypto and become a crypto VC, but she had doubts about her abilities and felt like an imposter (3m2s).
• Christina's concerns included wondering what she had accomplished and why anyone would take her money, comparing herself to others with more illustrious careers in Silicon Valley (3m17s).
• Christina was advised by a friend to either out-hustle people or pick something and go deep in it to become an expert, with the friend recommending crypto in the fall of 2012, which Christina did not take (4m9s).
• Christina decided to leave her job and learn how to code, with the goal of making things, rather than being an investor, and planned to live off her prior year's bonus while doing so (4m33s).
• The decision to leave was not easy, and Christina faced criticism and skepticism from others, who questioned why she would leave a good job and a prestigious company like USV (4m37s).
• Christina's plan was not to start a company immediately, but to teach herself how to code and make products, and she pitched this as a way to learn and grow, rather than as a startup (4m58s).
• Many people did not understand Christina's decision and thought she should stay at USV, work at another venture firm, or go to grad school, and some were even tougher, questioning her ability to make it on her own (5m49s).
• One person in particular, who had been close to Christina, was critical of her decision, saying that she was giving up the powerful part of her email address (the @usv.com part) and betting on herself, which was seen as a risk (5m51s).

Learning to Code and Personal Growth

• Despite the criticism, Christina went ahead with her plan and taught herself how to code, building a list of projects, most of which went nowhere, but which helped her learn and grow (6m32s).
• A period of self-improvement and learning was undertaken, where every day was treated as if going to a job, by getting dressed and going to a friend's office space in New York, to work on personal projects and learn new skills, such as Audacity tutorials and JavaScript, in order to create a sense of structure and routine (6m47s).
• The goal was to trick oneself into acting like having a job, in order to establish a daily routine and make progress on personal projects, and this approach was successful in creating a sense of normalcy and productivity (8m0s).
• A quote from the book "The Art of Fear" was mentioned, which states that the function of most artwork is to teach the creator how to make a small fraction of their work that is truly great, and this concept is also applicable to startups and businesses (8m46s).
• The idea that most successful startups and businesses are the result of trying many things and eventually finding something that works, rather than being the result of a single brilliant idea, was discussed, and this concept was learned from observing the experiences of startup founders at USV (9m53s).
• The notion that some people can create successful startups or businesses with their first or second idea is not representative of most people's experiences, and that trying many things and persevering is often necessary for success (9m45s).
• The importance of learning from failures and using them as opportunities to improve and learn was emphasized, and the idea that most people's successes are the result of trying many things and eventually finding something that works was reinforced (10m0s).

The Reality of Success and Business Models

• The idea of success is often romanticized, but the reality can be painful and unglamorous, with many people facing hunger and discouragement for years, both literally and metaphorically (10m3s).
• This romanticized notion can discourage people from starting their own businesses or pursuing their passions, as they may feel that their experiences don't match the idealized versions they see in movies or media (10m26s).
• The business model of relying on advertising can be flawed, as it often generates limited revenue per user, and companies should explore alternative ways to monetize their businesses (10m59s).
• A document called the Business Monetization Playbook was created to outline various ways to monetize a business, and it is available for free in the episode description (11m33s).

The Concept of "Bad Art" and Iteration

• The concept of "bad art" was introduced, which involves intentionally creating low-stakes, imperfect work to get past the initial stages of idea generation and skill development (11m49s).
• The analogy of muddy water in a hotel tap was used to illustrate the process of creating "bad art," where the initial output may be imperfect, but eventually, the water runs clear as skills and ideas improve (12m7s).
• This framework can be useful for anyone involved in creative endeavors or startups, as it acknowledges the importance of experimentation and iteration in the creative process (12m30s).
• An art teacher's assignment to make the perfect pot in five weeks was mentioned, where one student spent the entire semester crafting a single perfect pot, while another student made multiple pots a day, eventually producing better work through sheer volume and practice (12m45s).
• The concept of "300 pots" is mentioned, where having more attempts or tries can lead to better results, and it's essential to internalize this concept through experience (13m24s).

The Marshmallow Test and Startup Lessons

• A company experiment, inspired by the marshmallow test, was conducted, where teams were given limited supplies to build a tower with a marshmallow on top within an hour, and the team with the highest marshmallow won (13m32s).
• In this experiment, most teams, including the company team, initially approached the task by planning, segregating duties, and building the tower before adding the marshmallow, which often resulted in the tower collapsing due to the marshmallow's weight (14m2s).
• In contrast, when kids were given the same task, they would often put the marshmallow on the tower immediately and figure out how to support it, demonstrating an iterative approach to testing and risk assessment (14m47s).
• The importance of testing the riskiest assumption and not overanalyzing or overplanning is highlighted, as seen in the difference between kids' and adults' approaches to the marshmallow test (15m3s).

Building a Book Website and Discovering a Passion for Programming

• The founder of a company initially built a book website, similar to Goodreads, but without a clear plan or understanding of what they were doing, which led to confusion among others (15m17s).
• The founder was driven to build the website because they wanted it, despite it not being a viable business idea at the time, and they spent a lot of time battling JavaScript errors and learning from online resources (16m9s).
• The initial motivation for learning to code was to create something personally meaningful, such as animation when interacting with a digital book, which led to learning about CSS animation and building projects for personal use (16m20s).
• The realization that programming tools can be improved to make learning to code easier and more accessible to others sparked an interest in creating better programming environments (17m7s).

Finding the Right Startup Idea and the Birth of Vanta

• The startup trope advice that "build something you want" can be limiting due to personal experience, and a better approach is to find someone else with a problem and deeply understand them (17m48s).
• Another approach is to imagine the future and build it, but this can be challenging to generate reasonable startup ideas in the moment (18m3s).
• The idea for Vanta, a security company serving startups, came from recognizing a gap in the market where security tools were not being used by startups, despite being a huge market (18m41s).
• The interest in security stemmed from its competitive and cat-and-mouse nature, with a real-time dashboard of attackers and defenders (19m16s).
• The competitive aspect of security resonated with a personal trait of being very competitive (19m25s).
• Playing sports as a kid provided an outlet for excess energy, and working with the product security team at Dropbox was a great learning experience due to their fun and educational approach. (19m29s)
• When coming up with startup ideas, the goal was to find a deep and interesting space to work in for years, with the worst-case scenario being the acquisition of knowledge about internet security. (19m53s)

Working at Dropbox and Developing a Personal Accountability System

• After taking two years off to teach himself, a job was taken at Dropbox to gain experience working at a company and with people, as it was unclear if he was employable at the time. (20m20s)
• The story told to himself during this period was that he had to keep going, despite the evidence suggesting otherwise, in order to maintain a sense of confidence and self-worth. (21m9s)
• A personal accountability system was created using a Google form to track progress and goals, with the most important question being what would make him stop working on a project. (21m39s)
• This system helped him realize that his past self sometimes thought he should stop working on a project, but his present self always thought he should keep going, leading to a reevaluation of his approach. (22m1s)
• The experience of working on multiple projects and eventually stopping them due to a lack of progress taught him the importance of perseverance and self-awareness in the face of failure. (22m25s)

Managing Personal Psychology and Finding Centeredness

• Managing one's own mind and psychology is crucial, and figuring out what makes a person happy or centered is key to achieving this, with the importance of not giving up on these personal habits, regardless of how busy one gets (22m35s).
• For the individual, running three to four times a week serves as a mind-clearing, cathartic, and meditative activity that helps them feel centered, and it's essential to identify and prioritize such activities (23m16s).
• Reading is another activity that brings a sense of happiness and centeredness, having been a consistent hobby since childhood, and it serves as a way to learn and feel grounded (24m3s).
• Even with a busy schedule, it's possible to make time for these activities, such as replacing TV time with reading or utilizing commute time, like taking a bus to work, to read and have some personal time (24m35s).
• The individual still takes a bus to work, which allows them to have 20 minutes of uninterrupted time to read and relax, and they find this more beneficial than using a car and working on a laptop during the commute (24m58s).
• The importance of identifying personal habits and hobbies that bring happiness and a sense of self is emphasized, and it's essential to prioritize these activities to maintain a healthy and balanced life (23m41s).
• To stay centered and true to oneself, it's essential to stick with the things that make you feel like yourself, even when faced with self-doubt and uncertainty (25m48s).
• Managing one's own psychology is crucial when dealing with self-doubt, and having a conversation with oneself or telling a story to oneself can help, as it did for the individual who spent two years not landing where they wanted to (25m59s).
• The concept of BATNA (Best Alternative to a Negotiated Agreement) can be applied to life, where one's worst-case outcome is still a good one, and being aware of this can help with self-doubt (26m16s).

Building a Great Company and the Importance of Internal and External Factors

• Building a great company in Silicon Valley requires being a normal person internally, but having a 10% crazy factor externally, which can create an extra aura and lead to a 2x evaluation (26m48s).
• Looking back at past ideas and projects, it's common to realize that some ideas were good but not executed well, and that sticking with it or pivoting could have led to success (27m9s).
• The individual has worked on various projects, including art projects and a voice assistant for biologists, which were not commercially viable, but learned from these mistakes to build a company like Vanta with commercial viability baked in from the beginning (27m29s).
• When operating a business, it's essential to identify pain points, blind spots, and unaddressed parts of the market, and to think about what problems need solving (27m50s).
• The individual recommends looking into solving problems in the B2B SaaS space, particularly in the go-to-market tooling stack, which is currently fragmented and in need of a solution (28m26s).
• Another approach is to pick something you want to learn about and go talk to people about their experiences and challenges, as this can lead to new ideas and insights (28m51s).

Identifying a Problem and Validating the Solution

• The idea for a company was formed after experiencing problems with launching a product called Paper at Dropbox, which was blocked due to not having stock 2, and realizing that many startups face similar security issues (28m58s).
• The average startup does not have a security team to solve these problems, which led to exploring a potential solution (29m45s).
• Despite having coded 35 projects, the idea was tested with an Excel spreadsheet instead of writing code, and potential customers were asked if they would find the solution valuable (29m57s).
• The initial approach was to talk to one or two startups, including YC startups, to gauge interest in the potential solution (30m2s).
• The importance of validation was emphasized, and the need to frontload validation to determine if there is a market for the product (30m56s).
• A key challenge is avoiding false positives, where people express interest but do not intend to follow through, and it is essential to ask if they can implement the solution immediately (31m25s).
• When seeking feedback, it is crucial to talk to people who can make decisions and implement the solution, and to be cautious of responses that are not definitive, such as "maybe next quarter" (31m37s).
• The initial approach to finding people to talk to was to start with anyone who would engage in conversation, and then refine the target audience (31m50s).
• When networking, it's essential to make it easy for people to say yes to requests, such as following up with customized emails that can be easily forwarded to others (32m11s).
• To build connections, start with a brief meeting and then expand the network by asking for referrals and following up with new contacts (32m4s).
• The "mom test" is a helpful approach, which involves asking questions about the person's problem rather than the solution, as people can describe their problems but may not know the solution (32m47s).
• When conducting user research, it's crucial to avoid yes or no questions and instead ask open-ended questions that encourage the person to share their thoughts and feelings (33m0s).
• To build rapport, it's essential to use the same language and pronunciation as the person being interviewed, even if it's incorrect, to avoid making them feel uncomfortable or stupid (33m10s).

Vanta's Early Growth and Marketing Strategies

• Vanta's early growth strategy involved trying various approaches, including outbound emails to YC companies, and seeing what worked, with a focus on building a strong brand and word of mouth (34m30s).
• The company's founder sent cold outbound emails to YC founders, asking for feedback and then discussing their product, which helped get the ball rolling (34m25s).
• Vanta also built a strong presence in founder and VC slack channels, where people would recommend the company, helping to build a brand in people's minds (34m51s).
• However, the company faced challenges when knockoffs emerged, which affected their growth strategy (35m1s).
• The company had a billboard that read "Compliance that doesn't suck too much" which was still up and was equally as important as the software they made (35m6s).
• Podcast advertising was a successful marketing strategy in the early days, despite initial skepticism, and it still works today (35m25s).

Podcast Advertising and the Importance of Consistency

• Eric, a team member, pitched the idea of spending $20,000 on podcast advertising, which was initially met with skepticism but ultimately proved to be a good decision (35m40s).
• The idea that "consistency is overrated" was mentioned on the company's website, but it was meant as a joke and not a broad philosophical statement (36m15s).
• Consistency is actually underrated, and it's bad when the goalposts move, making it hard to find happiness (36m35s).
• The advice to keep moving the goalposts can lead to unhappiness, as it creates a never-ending cycle of chasing something new (36m51s).
• The key to happiness is not just achieving goals, but also enjoying the work itself, as many things are more sustainable when you like the work (37m46s).
• The formula for happiness is "progress equals happiness," where the sense of progress is what matters, not the current state (37m53s).
• Happiness is often associated with a sense of progress in a direction that one has intentionally set out and cares about, rather than achieving a specific goal, and moving the goalpost can be beneficial as it allows for continued progress and happiness (38m13s).

Founder Psychology and the Pursuit of Happiness

• Founder psychology can lead to unhappiness, even when a company is successful, as founders tend to focus on the downsides and the rollercoaster-like journey, rather than the overall progress (38m35s).
• High standards are not inherently bad, and having them can lead to a culture of excellence and a sense of community, where people care about their work and strive to improve (39m23s).
• Having high standards can be intimidating, but it can also be infectious and lead to a culture of excellence, as seen in companies like Vanta, where people are surrounded by others who are passionate about their work and strive to improve (40m10s).
• A leaked production document from MrBeast's team showed the high standards and expectations that the team has, and how it can be beneficial to have a culture of excellence, even if it's challenging (40m47s).
• MrBeast's company culture is an example of a "reality distortion field," where the leader's vision and expectations can inspire and motivate others to achieve great things (41m16s).
• Having a strong company culture and high standards can lead to a sense of community and excellence, where people are motivated to improve and achieve great things, even if it's challenging (41m21s).

The Impact of Surroundings and a "Why Not" Attitude

• A person's expectations and mindset about work, success, and timelines can be influenced by the people they surround themselves with, and being around someone who pushes past obstacles and has a "why not" attitude can be particularly impactful (41m35s).
• This mindset can be applied to both big and small things, and it's about deciding whether or not to pursue something, rather than assuming it's not possible (42m43s).
• Having a "why not" attitude can be helpful in achieving success, and it's possible to get used to a certain level of achievement and then strive for more (43m27s).

Fundraising and the Value of a Low Profile

• The company didn't raise funding early on, instead focusing on selling their product and reaching $10 million in ARR before raising their Series A, likely because they didn't need the funding at the time (43m33s).
• When the company did decide to raise funding, the experience was unusual because VCs in San Francisco were aware of their success through Slack channel chatter, but didn't know the full extent of it (44m3s).
• The company kept a low profile on purpose, preferring that others didn't know the details of their success, and this approach seemed to work in their favor (44m13s).
• A very smart and good VC was impressed by a pitch, particularly the AR ramp chart, which showed a significant increase to 10, and was left speechless, having expected a much lower number, around 2.5. (44m36s)
• Another VC, also very good at his job, had analyzed the company's Twitter chart, counted the pixels, and estimated the company's growth, impressing with his thoroughness. (45m11s)
• The experience of pitching to these VCs was enjoyable, despite not ultimately working with them, and was a moment to take pride in the company's achievements. (45m46s)
• Fundraising is still not a favorite activity, but talking about something believed in makes it more enjoyable. (46m6s)

Negotiation Skills and Vanta's Offering

• Eric thinks the person is great at negotiating, which is a surprising skill, and attributes it to confidence and a willingness to stand firm and not blink in negotiations. (46m18s)
• The company, Vanta, can be found at vanta.com, and offers help with security and compliance-related issues. (47m1s)