20VC Biggest Takeaways From Working With Paul Graham and Jessica Livingston, Why You Should Put Off Hiring For As Long As Possible & Why Seed Stage Investing Is All About Optimising The Top Of The Funnel with Harj Taggar, Founder & CEO @ Triplebyte

In this episode of "20 Minutes VC," host Harry Stebbings interviews Hajj Flemings, the founder and CEO of Triplebyte. Flemings discusses his journey from creating a Craigslist-style service for students to co-founding Automatic and its acquisition by Live Current Media. He reflects on his time as the first non-founding partner at Y Combinator, where he met his future Triplebyte co-founders. Emphasizing the importance of empathy in investors, he suggests that operational experience can be a proxy for this quality. Flemings also advises founders to delay hiring until they have a clear understanding of the roles needed and have experienced the related challenges firsthand. He envisions Triplebyte revolutionizing the engineering recruitment process by relying on skill evaluations over credentials, aiming to make traditional hiring seem outdated in five years. Throughout, Stebbings promotes sleep and productivity solutions, Simba Hybrid and Cirrus Insight, as part of his new year's routine.

• Harry Stebbings is the host of the 20 minutes vc podcast.
• Harry is active on Snapchat and writes on mojitovc.com.
• He invites listeners to share their thoughts and feedback.

We are back and you are listening to the 20 minutes vc with your host Harry Stebings, found most commonly on Snapchat at htebbings with two B's, and also writing some more academic, thoughtful pieces these days on mojitovc.com.

The quote provides an introduction to the podcast and the host, Harry Stebbings, mentioning his social media presence and writing endeavors.

• Hajj Taggar is the founder and CEO of Triplebyte.
• Triplebyte focuses on changing engineering recruitment by evaluating tech skills over credentials.
• Hajj was the first partner at Y Combinator after its founding and co-founded Automatic, which was acquired by Live Current Media.

I'm delighted to welcome a fellow Brit in the form of Hajj to Gar. Now Hajj is the founder and CEO at Triplebyte, the startup that is changing the world of engineering recruitment by building a new kind of interview that evaluates tech skills, not credentials.

The quote introduces Hajj Taggar and his company, Triplebyte, highlighting its innovative approach to engineering recruitment.

• Harry aims to sleep more, using the Simba hybrid mattress.
• He also targets increased productivity, using Cirrus Insight to integrate with Salesforce.

With the new year comes new routines and one of mine is sleeping more. And that's where the Simba hybrid comes in. Another target of mine for the new year is productivity, and there's no better for that than Cirrus insight.

The quote outlines Harry's personal New Year's resolutions related to improving sleep and productivity, mentioning the products he uses to achieve these goals.

• Hajj is originally from England and started a Craigslist-like service for students.
• After gaining traction, he applied to Y Combinator and moved to Silicon Valley.
• Following an acquisition by Live Current Media, he joined Y Combinator as a venture partner and later as the first non-founding partner.

I'm originally from England, as you can probably tell. And during college, I had started working on what was a side project at the time, which was to just launch a simple Craigslist type service for students at our university to buy and sell things to each other.

The quote details Hajj's early entrepreneurial efforts that eventually led him to Silicon Valley and Y Combinator.

• Hajj reflects on working with Y Combinator founders Paul Graham and Jessica Livingston.
• He acknowledges their stature within the programming and startup communities.
• Hajj was aware of the opportunity to work with influential figures in the tech industry.

Paul and Jessica were, they were a big deal within the Y combinator community, and I think working alongside them, I was kind of aware that I was really lucky to be able to work with both of them.

The quote provides insight into Hajj's experience working with Paul Graham and Jessica Livingston, emphasizing their significance in the community and his appreciation for the opportunity.

• Hajj was surprised to find that all startups have serious problems.
• He realized that his own startup was not unique in facing challenges.
• The intensity of startup issues was eye-opening for him.

I remember doing my first sort of office hours and thinking, wow, all of these companies have really serious problems. I could think of a reason why each of these companies is likely to not be around next month.

The quote reveals Hajj's initial surprise at the universal challenges faced by startups at Y Combinator, which was a stark realization compared to his previous belief about his own startup's unique struggles.

• Startups often present an image of success, hiding their internal issues.
• Founders may not realize that all startups face existential threats.
• It's common to think that one's own startup is uniquely troubled.

"No matter how problematic or screwed your startup is, everyone always presents externally that things are going fantastically."

This quote emphasizes the disparity between the outward facade of success that startups maintain and the internal struggles they face, which are common to all startups but often not discussed openly.

• Startups should primarily focus on internal operations to avoid failure.
• Internal mistakes are more likely to be fatal than external competition.
• Awareness of competitors is necessary for funding and hiring top talent.
• Founders need to understand their market and competitors to demonstrate domain expertise.

"Operationally you need to be focused on your company above all else and not be worried about competitors. But you need to know enough about what your competitors are doing to seem like, or to generally actually have domain expertise and talk credibly about the market you're operating in."

The quote addresses the balance between concentrating on internal startup processes and having sufficient knowledge of competitors to establish credibility in the market and industry.

• Early-stage startups are often unstructured and operate informally.
• Startups may begin with just a few people working from an apartment.
• Y Combinator provides structure and a sense of reality to startups.
• Realness in a startup is not tied to funding but to having active users.

"What most people don't get is that an early stage startup doesn't feel real."

This quote captures the essence of the early stages of startups, where the lack of traditional business infrastructure can make the endeavor feel less legitimate until certain milestones, such as user acquisition, are reached.

• Realness in a startup is associated with having a growing user base.
• Hiring employees adds a sense of responsibility and seriousness.
• Founders often feel that their startup is genuine when they acquire real users.
• The growth rate is important, but having a dedicated user base is crucial.

"The only moment you feel like you have a real company is when you have a clear set of users and that number of users is growing."

This quote highlights the moment when founders typically feel their startup has become a legitimate entity, which is when they have an identifiable and growing user base.

• Growth in startups can be challenging to measure, especially for investors.
• Y Combinator's short feedback loops contrast with the longer ones for most investors.
• Paul Graham's vision for Y Combinator was to create a holding company structure of autonomous, successful units.

"One of the most compelling high level thoughts that Paul shared with me that got me really excited about joining YC was he explained it in terms of how he thought corporations, or just big companies, would be structured in the future."

This quote reflects Paul Graham's forward-thinking approach to Y Combinator's structure, envisioning it as a large entity composed of smaller, independent companies, and how this vision influenced the speaker's decision to join YC.

• Y Combinator (YC) aimed to fund a large number of companies, knowing that while most wouldn't become large, they could still add value to the network.
• Growth at YC was driven by the desire to fund all promising applicants, with the batches of funded companies expanding to not miss out on global talent.
• The internal focus was on identifying and funding good companies, with the understanding that logistics and experience quality for larger batches would need to be figured out subsequently.

"The true north of Y combinator was this idea of if we could fund hundreds and hundreds of companies, some of them would grow to be really large." "So the growth of YC was defined as of the applicants every cycle. We want to make sure that we're funding all the good ones."

The quotes highlight Y Combinator's strategic goal of funding a vast array of startups, with the understanding that while not all would be highly successful, each could contribute to the overall ecosystem, and the importance placed on not missing out on funding potentially successful companies.

• Operational experience in investors is valued for its correlation with empathy towards founders.
• Empathy is crucial for investors to understand the stress and difficulty of starting a company.
• Founders should assess investors' track records and get references from other founders they've worked with.
• Some investors, like Peter Fenton, demonstrate deep empathy without having been operators themselves.

"I'm a pretty strong believer that operational experience is pretty important to have in investors." "I think you need to have deep empathy for how difficult it is for founders and how sort of pressurized they are all the time."

These quotes emphasize the importance of investors having empathy for founders, which often stems from operational experience, and the necessity for founders to seek investors who can truly understand and support them through the challenges of starting a company.

• As a seed stage investor, the focus is on optimizing the top of the investment funnel.
• Hard work and helping founders, even without investing, can generate positive word of mouth.
• Building a strong portfolio requires being known among founders and being recommended for future funding rounds.

"A seed stage investor is really about optimizing the top of your funnel." "And the way that that happens is by just working really, really hard for lots of founders, whether you've invested in them or not."

The quotes discuss the importance of seed stage investors working hard to establish their presence among founders and the significance of building a reputation that encourages founders to seek them out for investment, highlighting the effort required to be successful in this role.

• Early stage startups should delay hiring as long as possible to ensure a clear understanding of roles and requirements.
• Raising venture capital (VC) prematurely can pressure startups to hire before they are ready.
• Founders need firsthand experience with their product and sales process to effectively hire and manage new team members.
• Managing people is challenging, especially for first-time founders, and should be approached with caution.

"Step one, I think you actually want to put off hiring as an early stage startup for as long as you possibly can." "You want to be hiring because you feel so overworked from all of the things that need to get done and you have a very crisp idea in your head of who you would hire."

These quotes outline the advised approach to hiring for early stage startups, suggesting that hiring should be delayed until founders have a deep, practical understanding of the necessary roles and the challenges associated with managing a team. It also touches on the complexities and potential pitfalls of hiring too early, particularly when driven by external pressures from investors.

• Startups should avoid simultaneous pressures of finding product-market fit and scaling the team.
• Focus should be on either finding product-market fit with a small team or scaling and growing once fit is established.

"You either want to be focused with as small as possible team on finding product market fit, or you want to realize you have product market fit and just be in full on growing, scaling the team and making a functioning organization."

This quote emphasizes the importance of startups focusing on either discovery (finding product-market fit) or growth (scaling the team), but not both at the same time, to avoid compounded pressures.

• Enjoying one's work is akin to not working a day in life.
• Finding something that naturally occupies your thoughts can lead to great work.

"That's how you do great work, is to find something that you just naturally are thinking about a lot."

The quote suggests that passion for one’s work, where it does not feel like work, is the key to achieving excellence.

• Being a good seed stage investor involves enjoying meeting and helping people with no expectations in return.

"That's also how you're a good seed stage investor is to just generally enjoy meeting and helping people without expecting anything in return."

This quote suggests that a successful seed stage investor should derive satisfaction from the process of engaging with and assisting others, rather than focusing solely on potential returns.

• Richard Feynman's autobiography provides insight into how passion leads to mastery.
• The book exemplifies how continuous engagement with one's interests can lead to significant achievements.

"Surely you're joking, Mr. Feynman. Richard Feynman's autobiography. And why? Because I think it's like just the best insight into how you get really good at something you love to do."

The quote explains that the autobiography of Richard Feynman is valued for its demonstration of how deep engagement with a subject one loves can lead to mastery.

• Being CEO of Apple, even for a day, would provide unique insights into leading the world's largest corporation.

"I just think Apple remains an incredibly unique company and seeing, experiencing, even for a day, what it's like to be the CEO of the largest corporation in the world would be a really interesting insight, no?"

The quote expresses a curiosity about the experience of leading a major company like Apple and the unique perspective it would offer.

• Paul Graham became a mentor after his essay on startup mistakes resonated with the speaker's experience.
• The relationship with Paul Graham started from seeking advice on avoiding common startup pitfalls.

"I would have to say Paul Graham on this one. I'd spent so many years working with him."

The quote identifies Paul Graham as a significant mentor due to the years of working together and his influence on the speaker's approach to startups.

• Slate Star Codex is recommended for its clear writing and insightful commentary on key issues.

"I would actually say Slate Star Codex. I've only gotten into reading the archives recently."

This quote suggests that Slate Star Codex is a valuable resource for thoughtful analysis and is recommended for readers interested in rationalist perspectives.

• Competency should be prioritized over personal likeability in hiring for startups.
• Predicting personal compatibility is difficult, and working relationships can evolve based on professional competence.

"You want to be around people who are just really good at what they do more so than whether you like them personally or not."

The quote challenges the common startup hiring practice of prioritizing personal likeability, advocating for a focus on professional skill and competence instead.

• The grand vision for Triplebyte is to render traditional hiring processes obsolete through data-driven screening.
• In five years, using Triplebyte for hiring should be as standard as using established databases for technical needs.

"The grand vision for Triplebyte is to make the current hiring process just seem outdated five years from now."

This quote outlines the ambitious goal for Triplebyte to revolutionize the hiring process by leveraging data to improve hiring decisions.

• The speaker emphasizes the importance of personal routines for growth, such as getting more sleep and enhancing productivity.
• Tools like Simba Hybrid and Cirrus Insight are highlighted for their contributions to sleep quality and productivity, respectively.

"And with the new year we need new routines. And as I said earlier, one of mine is sleeping more and that's where Simba hybrid comes in."

The quote reflects the speaker's commitment to personal development and the role of products and routines in achieving a more productive lifestyle.