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· 3 min read
Liz Yang

In an era where technological evolution is rapid and relentless, the emergence of Large Language Models (LLMs) represents a significant leap. The LLM infra stack, a complex and multi-layered architecture, plays a pivotal role in enabling these models to function effectively in various applications. This blog post delves into the intricacies of the LLM infra stack, exploring its different layers and the challenges associated with each.

The Four Layers of the LLM Infra Stack

  1. Data Layer: At the foundation lies the data layer. It's not just about having data; it's about having the right data. This layer involves the storage and processing of data, which is crucial for the LLMs to generate accurate and relevant outputs. An interesting concept in this layer is Retrieval-Augmented Generation (RAG), which aids LLMs by providing them with the necessary data to respond appropriately, minimizing hallucinations and inaccuracies.
  2. Model Layer: The model layer is where the actual Large Language Models reside. These models are complex and require substantial computational resources. They are large, slow, and expensive, and present novel challenges such as unpredictable behavior and the need for in-context learning.
  3. Deployment Layer: Deploying LLMs in production environments is a challenging task. The deployment layer involves making these models accessible and usable in real-world applications. This includes ensuring performance reliability, managing costs, and maintaining observability.
  4. Interface Layer: The final layer is the interface through which users interact with the LLMs. This layer must be intuitive and user-friendly, allowing users to leverage the power of LLMs without needing to understand the underlying complexities.

Challenges and Opportunities

Each layer of the LLM infra stack comes with its unique set of challenges. For instance, in the data layer, the challenge lies in creating effective ELT (Extract, Load, Transform) pipelines and ensuring the data is featurized appropriately for efficient retrieval. In the model layer, managing the size and complexity of the models is a significant hurdle. The deployment layer faces challenges in building infrastructure that can support the heavy demands of LLMs, while the interface layer must bridge the gap between complex technology and end-user accessibility.

However, these challenges also present opportunities. There is a growing need for sophisticated infrastructure to support these layers. This includes the development of new database technologies optimized for vector embeddings in the data layer and the evolution of tooling and design patterns for deploying and interfacing with LLMs.


The LLM infra stack is a dynamic and evolving space, presenting both challenges and opportunities. As we navigate through its layers, from the foundational data layer to the user-facing interface layer, it's clear that a deep understanding of each component is crucial for harnessing the full potential of Large Language Models. The future of LLMs is bright, and their impact on various industries is bound to be significant, provided we continue to innovate and adapt in developing the infrastructure that supports them.

· 2 min read
Liz Yang

I am thrilled to announce a significant development for our tech community, which brings together cross-functional (XFN) leaders from the vibrant hubs of Silicon Valley, Seattle, and New York City. Today marks a new chapter in our journey of growth and discovery.

We are officially publishing the full list of companies that our community has meticulously reviewed on our platform. This treasure trove of information is now available at

Why This Matters

In a world where innovation, investment, and leadership intersect, knowledge is power. Our community has been at the forefront of evaluating and discussing some of the most dynamic and promising companies in the tech sector. By sharing these reviews publicly, we aim to:

  1. Foster Transparency: Showcasing the companies we've reviewed brings a new level of transparency to our community. It allows everyone to see the breadth and depth of our collective insights.

  2. Encourage Collaboration: This publication is not just a list; it's a platform for collaboration. We invite members and the wider community to engage, share their thoughts, and build on the reviews.

  3. Support Informed Decision-Making: For investors and leaders, this is a valuable resource. The insights and analysis provided can guide decisions in investment and partnership opportunities.

What You'll Find

The page is more than just a directory. Each company listed comes with a comprehensive review covering various aspects such as innovation potential, market positioning, leadership strength, and much more. These reviews are the product of rigorous analysis and thoughtful discussion among our community members. You can request for memo on the page.

Get Involved

This is just the beginning. We encourage our members to contribute further reviews and insights, continually enriching this resource. If you're not yet a member but are an XFN leader passionate about tech, innovation, and growth, we invite you to help us source deas and information. Together, we can 10x our growth in innovation, investment, and leadership.

Thank you for being a part of this exciting journey. Here's to our continued growth and success!

· 9 min read
Yiyang Hibner

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Can you please introduce yourself as if you were catching up with an old friend?

We often introduce ourselves with a specific job and title, e.g. “I’m a [TITLE] at [COMPANY]”. However, when I think about who I am now, it goes beyond a specific job title. I’ve been fortunate to have multiple titles and experiences in large corporations and mid-size startups, though that’s just one part of the story of who I am.

So if I were to introduce myself as if I were catching up with an old friend, I would share what I’ve learned through the course of my career and how I’ve grown through those experiences.

-- I’ve spent my career in product management growing from ground zero as an associate and working my way up to executive leadership roles at large companies and mid-size startups.

-- I’m a mother of four children so let’s just say that I’m comfortable with chaos! It also gives me a bigger picture perspective when approaching challenges at work and supporting my team.

-- I’m a seasoned leader with 20+ years in the tech industry, where I’ve witnessed the ever-evolving landscape of technology from the beginnings of mobile to new technological advances with AI. I’ve also experienced the highs and lows of the tech industry, from times of high growth to the focus on efficiency during the downturn.

Wow this is so beautifully said! You have had a very successful 17-year career at Google. When you joined as an Associate Product Manager, what was your career goal then? Did you ever imagine growing to a Senior Director role?

To be honest, I didn’t have a meticulously laid-out plan, or at least one that I ended up following 😀. In school, I majored in computer science, but I had a hunch that my career path would likely involve a fusion of business and technology. However, I wasn't entirely clear about the role of product management – and certainly not the differences between product manager, project manager, and program manager, for that matter!

My original plan was to study computer science, work as a software engineer, and then pursue an MBA. However, when I landed the opportunity to join Google's APM program, I decided to take a leap and learn as I go! I had minimal knowledge about product management when I started, to the point where I had to Google what a "PRD" was! It was a journey of trial and error, and I had to learn on the go. The advantage was that I didn't have preconceived notions, so I was open to experimenting and discovering what worked. This approach still influences my approach to learn and adapt in different workplace environments today.

My advice to others is to set a general direction for your career and stay open to evolution as you gain experience and insight. Don't just focus on the immediate next step, as that may lead to optimizing for the short term. Instead, consider the long term and think a couple of steps ahead, then work backward to build your path.

Anything you wish you had done differently at Google?

I generally prefer to not dwell on regrets, but I do believe that life doesn't always unfold according to plans. However, in hindsight, I’ve come to learn that there’s still value and wisdom gained even when things didn’t go as intended. In fact, sometimes the deviations from our plans end up leading to unexpected, and often better, outcomes – a lesson I've come to embrace over time.

As my career progressed, I held onto a fundamental philosophy instilled in me by my parents from a young age: work hard. It served me well during my college years, but eventually, I hit a point where pushing harder and sacrificing sleep could only take me so far. I realized that working tirelessly wasn't always the solution. There are moments when taking a step back, considering the people involved, and understanding the dynamics at play become just as crucial, if not more so, than simply working harder. Life isn't always fair, and it often throws unexpected twists and turns our way. This realization has been an evolving lesson throughout my career journey.

Which part of the promotion process felt the hardest for you at Google?

I often joke that preparing a promotion packet at a large company like Google can feel like defending a PhD thesis (or at least the intensity that I imagine as I don’t hold a PhD myself). The process can often involve iterating through the packet multiple times along with a lot of work behind the scenes to make the case.

Sometimes the trickiest part is knowing when is the right time to go for that promotion. Personally, I grappled with feelings of self-doubt, and at times feared the possibility of rejection so much so that I was willing to delay trying. And I’ll be honest, getting a “No” in a packet certainly does sting and hurt your ego. However, with the benefit of hindsight, I’ve come to realize that not trying is the same as a rejection, the difference is your ego.

So my recommendation is to understand which way you lean… do you lean conservative or aggressive going for promotion? Given that understanding, you can then find ways to balance yourself out for a more thoughtful approach. For those who lean like me, there will be times when you should take that leap, understanding that the worst-case scenario is a temporary ego hit if things don't go your way.

Who impacted you or inspired you the most in your life?

In my professional journey, I consider myself incredibly fortunate to have had exceptional managers early in my career. They set a high bar for what it means to be a great manager, and I was determined to follow in their footsteps and pay it forward when I eventually became a manager myself. Their influence laid a strong foundation, one that I still carry with me. I can vividly recall the feelings I had while working with those managers – a sense of purpose, acknowledgment, and the thrill of being challenged. These emotions serve as a constant reminder of how to motivate and inspire my own team.

On a personal note, the person who has had the most profound influence on me is undoubtedly my mother. She faced a lifelong battle with mental illness and disorders, starting with postpartum depression after my birth and escalating from there. It may sound unusual to label this as an inspiration, but through her struggles, I developed a deep well of empathy. This empathy has proven invaluable in my career, allowing me to connect with customers and users on a profound level, to discern the unspoken feelings behind their words.

It's easy to place managers and leaders on pedestals, expecting them to have all the answers, but they are human too. The same applies to our parents; they are also human, as I've come to understand more profoundly since becoming a parent myself. Recognizing this human aspect in managers and leaders, acknowledging their struggles and insecurities, adds a new layer of perspective. It reminds us that perfection isn't the goal, and sometimes unexpected or challenging experiences in our lives can provide a richer perspective and become a source of strength.

What are some skills you have to learn v.s. Unlearn as a career coach compared to a product executive?

Right now, my primary focus is coaching leaders in product and tech where I spent the past couple decades of my career, so I can relate to their challenges and best support them.

However, there's a crucial skill to unlearn in this new role. As a coach, it can be tempting to jump into problem-solving mode, but it's essential to remember that you're not a manager, and you don't possess the complete context of their organization. The information you receive is often filtered through the lens of a single person's perspective. Thus, your role isn't primarily about solving the problem outright or dictating a solution. Instead, it's about supporting and empowering the individual.

It's a shift from "how do we solve the problem" to "how can I support you in becoming the best version of yourself to address the situation at hand." The emphasis lies in the person rather than the specific problem as a priority.

What are some things people normally don’t know about you?

People may not know, or expect, that I’m actually quite comfortable with different extremes of personalities!

Personally, I tend to gravitate towards a calmer disposition, a trait possibly influenced by my father's role as a Daoist priest. However, my upbringing was characterized by a stark contrast, as my mother is quite expressive and occasionally uses colorful language in Chinese 😁.

As a result, I've grown comfortable in workplace settings with individuals at both ends of the personality spectrum. I'm at ease with those who are more outspoken or swear often, understanding that such traits don't necessarily imply unkindness. I’m also comfortable with those who are more introverted or choose their words carefully.

The valuable lesson here is that while this is a part of who I am, there exists a rich tapestry of personalities and leadership styles in the world. I am genuinely comfortable interacting with individuals possessing a wide range of personalities, whether they align with or differ from my own disposition.

If our readers are interested in learning more about your coaching, how should they reach out? Do you have any limitations on what kind of clients you take?

The most straightforward way to connect with me is through LinkedIn, where you can find links to reach out or schedule time with me. Coaching, for me, is a deep-seated passion, and it's all about how I can assist you on a personal level, transcending the boundaries of job titles or career stages. I work with individuals across a wide spectrum, focusing on understanding their unique needs and delivering value accordingly.

· 3 min read
Liz Yang

The meeting conducted on November 5, 2023, presented a review of potential investment opportunities. Below is a concise evaluation of each opportunity based on the discussions.


  • Puzzle is venturing into the accounting software market with a Series A+ round seeking $30M at a $120M pre-money valuation.
  • Despite pre-revenue status, projections show promising growth (ARR from $0.4M in Q4 2023 to $24.3M by 2025).
  • The company targets a significant market gap due to a 17% decline in U.S. accountants and auditors since 2019.
  • Challenges faced by legacy systems and the role of AI in expense categorization were discussed. The comparison to older systems like Netsuite suggests a competitive edge but also raises questions about market penetration capabilities.
  • The global fund administration services industry was worth at least $8 to $12 billion as of August 2021. ([]( global fund a))
  • 87

Wobot Intelligence

  • Wobot, at the Seed+ stage, is raising $2M with a convertible note capped at $20M.
  • The company offers a no-code AI video intelligence platform with $100K MRR and significant U.S. revenue, poised for growth.
  • Questions regarding the efficacy of computer vision over existing security systems and the reliability of the India-based team were raised.


  • Grayce is a Series A stage company raising $10M at a $26M pre-money valuation.
  • It provides a family caregiving platform with a growing customer base and has shown 230% YoY growth.
  • The scalability and complexity of competing with insurance companies were noted as potential challenges.

Atomic AI

  • Seeking $20M SAFE in Series A+, Atomic AI focuses on fusing AI with structural biology for RNA drug discovery.
  • The field is complex, and further expertise is needed to fully grasp the potential and risks associated with this opportunity.


  • Velvet, in the Seed stage, is raising $4M at a $20M post-money valuation.
  • It aims to utilize generative AI to create a transparent data layer for the private market, expanding from a marketplace to SaaS for VCs.
  • The platform's place in the current market hierarchy and the difficulty of entering relationship-driven business were discussed.


  • WorldCoin is in the process of raising $500M at a pre-money valuation of $3B.
  • They are working on a large-scale privacy-preserving identity network, with significant backing but also facing privacy concerns.
  • The ethical implications of biometric data collection and competition with established ventures like Nasdaq Private Market were considered.

The evaluation of these opportunities should continue with a balanced view of their potential against market realities and inherent risks. Further due diligence is recommended before proceeding with any potential investment.

· 5 min read
Yiyang Hibner

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Q: Who impacted you the most in your life? A: Professionally it would be my personal board of directors - which is a group of trusted advisors, who know you intimately, and who really have a vested interest in your success. They will not only be supportive and be your biggest cheerleader, but they will also give you the hard truth, about where you are in your career and what your development areas are, and if you're ready for the next role or not. My personal board of directors was my sounding board when I was dealing with leadership challenges as a COO or a VP Product, and they also helped me think through career transitions. My board opened doors for me to land a VC role, and also helped me recently think through whether I was ready for a CEO role or not. I wrote more about how my board has helped me, and how you can go about building your personal board of directors here.

Personally, I am married with three amazing boys. I don't think I could do the work I do without a loving and supportive partner. As Sheryl Sandberg says, you need to find a partner who will share 50/50 in household chores, raising the kids, and supporting your career. My husband Cary is an employment attorney who works for himself, so he has more flexibility with his schedule. There have been times when I've worked 70-90 hours a week, and he's taken on more of the household chores and childcare. When I was on Sabbatical, I did lots of solo traveling, and he drove the kids around more. This is what it means to be in a 50/50 partnership: sharing responsibilities equally, even if that means one person takes on more of the load at different times.

Q: You have pivoted your career a few times. From being a startup operator and then to VC and now as a startup fractional COO and advisor, what are some considerations you have made before you officially made the switch?

A: I've always taken stock of my career to make sure I'm still learning and growing. I get bored easily and need to keep moving fast. If I feel stagnant, it's time for a new challenge.

In my first 10 years in tech (2000-2010), I was focused on climbing the corporate ladder. I started as a product manager and quickly moved up to manager, director, and then VP. After 16 years, I felt like I had mastered the product leadership role and was ready for something new.

During my first Sabbatical in 2015, I had a conversation with my old boss from eBay, who had joined a venture capital firm. She offered me a position as an EIR (Executive in Residence). In this role, I helped Omidyar Network’s portfolio companies with product strategy, organizational design, and design sprints. After 6 months, I was offered a full-time position as an operating partner. I eventually moved over to the investment team and started investing in tech startups.

After 5 years of VC, I was wondering: do I want to continue to build? I truly missed building products so I went back to a startup operating role and joined Swimply as their Chief Experiences Officer.

Q: What are some ways that you relax? .. A: I am a big poker player so you will find me in Vegas maybe six times a year playing poker. My website is You can see a few pictures of me there at the final table of the World Poker Tour (WPT) tournament. I also love watching college football so I combine this when doing laundry. Fall is my favorite time of the year, where I spend all Saturdays doing five or six loads of laundry (with a big household) and turning the TV on. I also love cooking and hosting dinner parties. I also believe in human connection so I enjoy meeting people and connecting with them one-on-one. Of course, I love international travel, so I do a lot of international traveling as well. I just came back from being in Paris for 2-weeks where I dropped off my oldest son at college for the semester there.

Q: What are some recent books or tv shows that you recommend? A: I do a lot of audiobooks. Principles by Ray Dalio is a really good book. Every time I did a pivot into a new career, I would read related books, e.g Venture Deals by Brad Feld and Jason Mendelson is great for anyone interested in VC and startups. Another book in terms of being a great c-suite leader is called Startup CXO. Another favorite business book is called Leading with Heart by John Baird & Edward Sullivan, and it’s about how you can really become the best people leader.

· 6 min read
Yiyang Hibner

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Guest post author: Chris Tyler I believe experience and the people you work with are the most important forms of compensation when choosing a job. That said, money matters too. A feeling that you’re not adequately compensated can erode all other positive factors associated with a job. Understanding the potential upside of a job is important, and I wish I had been more aware of earning potential when selecting Product Manager roles in the past. In this post I share what I’ve learned about compensation after 14 years of working in Product Management at companies in various stages of growth: 0 to 1, growth stage and post IPO (Meta and Zynga).

There are two forms of compensation:

  1. Cash - base salary + bonus
  2. Equity - either in the form of shares / options at pre-IPO startups or Restricted Stock Units (RSUs) at public companies

You’ll never get rich from cash compensation - equity is how you build wealth. Real estate developer Moses Kagan summarizes this well: The game is effectively converting your work into ownership of productive assets. Or, as Warren Buffet has said: If you don't find a way to make money while you sleep, you will work until you die.

So, building equity is important, but equity compensation is poorly understood by many job seekers in tech. I’ve seen a lot of “I’m joining this company and getting some options, and I hope they’re worth something someday.” Employers contribute to this dynamic by withholding information about the equity from candidates who have job offers.

Below are the four primary types I’ve jobs I’ve seen available in the tech / PM world and the cash / equity compensation potential with each of them:

1. Starting a company

Living the dream: eating ramen, grinding 24/7 and brining something new into the world.

  • Cash: minimal

  • Equity: high to medium - you (and your co-founders) start off with all the equity, but the need for cash (and/or validation and prestige) often has early stage founders dilute their equity soon after founding. If you do raise money, make sure you understand the terms.

  • Risk Profile: high - most startups fail. You can de-risk by starting a company while at your full-time job. This was always my dream, but I was never successful at mailing it in at my W-2 job and creating the space to start something new.

2. Joining an early stage startup

*Joining a seed stage startup - you’re probably employee # 1-20 at a Seed / Series A company. Still grinding to bring something new into the world.

  • Cash: minimal, but higher than startup founder*

  • Equity: tiny - the drop off from founder to employee #1 is huge. This simple, illustrative cap table is directionally correct for a Series A company. The percent of stock owned by ALL employees is 4.2%. Founders get 20.6%, and the rest goes to investors. Not only do investors have the lion’s share of equity; they also have preferred equity that usually includes a liquidation preference. It’s worth understanding all of these terms. tl;dr - your common equity is probably not worth much unless things go really well.

  • Risk Profile: high - most companies at this stage don’t have strong product / market fit and few will escape to become a growth stage company.

3. Joining a growth stage company

Growth stage companies are typically larger (100+ employees), have raised more money (Series B and beyond). Wealthfront’s Career Launching Companies is a great list of growth stage companies.

  • Cash: Moderate to strong - will be close to or same as cash from a public company

  • Equity: tinier - remember the prior example where the employees had 4.2% of equity? It’s likely to be even more compressed after multiple rounds of fundraising, and the majority of the equity will be earmarked for senior hires (VP+). And these companies often have lofty valuations that will be hard to exceed via an IPO. Your outcome here is closely tied to continued growth of the company.

  • Risk Profile: moderate - you’re de-risking the cash element, just make sure you can estimate what the equity is worth.

4. Joining a public company

FAANG PM jobs are a different animal - the job is much more about strategy and alignment. “Influence without authority” is the name of the game. Oh, and the comp is awesome.

  • Cash: strong - you’re getting paid top of market, and your equity is effectively cash as well.

  • Equity: tiniest - BUT: although your ownership of the company is tiny, it’s also liquid: you can sell your shares at any time. Equity increases dramatically the more senior you become and is how you build wealth working at a larger company.

  • Risk Profile: minimal - you have liquidity and a clear line of sight into what your equity is worth. The biggest risk is macroeconomic factors hurting the value of the stock - from 2021 to 2022 I saw Meta stock fall from $360 to $88, and this had a huge impact on my compensation.

My summary thoughts on the data points above:

  1. Don’t work a startup or growth stage company to get wealthy. The cards are stacked against you. The best reason to join a company in these phases is experience. Go in eyes wide open about what your shares might be worth - this article provides a good primer on how to do this.

  2. If you’re optimizing for compensation, working at a public company (especially one that pays top of market, like Meta or Google) is the way to get rich. Keep racking up those RSUs, and if you’re lucky, the stock price goes up, benefitting you even more. (It’s good to be an owner!)

About a year go I found myself in a conundrum: I was liking the compensation from working at a public company, but the hours and the work were not lighting me up. I wanted the equity / ownership that comes with a startup, but I didn’t want to start my own thing.

I ended up learning about and pursuing another way to get significant ownership: Entrepreneurship Through Acquisition. I’m currently doing a “search fund” - I have raised money from investors to fund a two year search for a business to buy. The investors fund the acquisition of the business, and I will operate and improve the business as CEO. This gives me the equity potential of starting a business from scratch with the salary and certainty of a growth stage company.

If you’re interested in following my journey to acquire and operate a company, you can read my newsletter at

I’m also teaching a course on Maven in Sept 2023 about how to acquire a company.

· 8 min read
Yiyang Hibner

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Guest post: David Marc Siegel

I’ve always been interested in music. I took piano lessons from the ages of 5 to 13 - but stopped since I was mostly learning classical and classical wasn’t what greatly fired my imagination at that age. Somewhere in the middle there while also listening to all the pop music of the day, I got really into “Weird Al” Yankovic - this is back when he first showed up singing “Eat It.” Blew my mind.

Over the years, I got even more into novelty, comedy and more broadly off-kilter music, collecting all the Dr. Demento tapes & Firesign Theatre albums I could find. This music was a sort of initiation into a world where a song could be whatever you wanted it to be - you didn’t have to be aiming for the pop charts, but you could still be expressing yourself in a critical and legitimate (and explicitly strange & counter-to-trend) way. Explorations into Devo and the alternative explosion of music through the 90’s furthered this notion for me. As I later discovered, many of the more influential musicians through the 20th century had this strong “outsider” self-identification, perhaps culminating in bands like Nirvana and the general first wave of grunge.

I started studying guitar and became enamored of bands like REM, whose notions of expression were subtle and ran counter to the gender-typical, hairspray-heavy music of the late 80’s. I got deep into music theory and jazz, got into jam band music, saw the Grateful Dead and Phish a bunch, and played in some art punk & indie rock bands that generally fell apart in predictable (though not particularly dramatic) ways. One such band got an album in the CMJ charts top 100.

At this point in my life, my social life was largely playing music - I’d get together with friends to jam; I helped put together a monthly cabaret night in the Western Addition neighborhood of San Francisco where we’d present various artists & musicians, some of whom have gone on to great heights - which ran for several years; and so on. As work & romantic relationships developed (and perhaps fell apart), life situations changed - and musicians are a bit of a constantly-moving lot, and so these situations, too, slowly phased out as we all entered into different phases of our respective lives & had to prioritize other considerations.

I spent a few years writing music for medium-scale theatrical productions, sketch comedy shows and even for online advertisements. I loved this work because it allowed me to get outside of myself as I wrote songs - and leverage composition in ways that focused on it being more an aspect of storytelling than just musical presentation for the sake of music. A director needed a song that solved a certain problem - gave a “beachy” vibe; sounded “inspirational” in a specific way; sounded like an opera; and so on. These were thrilling because so many of those projects were the first time I was doing that particular style or form - and so I’d study examples, understand how they worked and were arranged & orchestrated, and try my best. And people seemed pretty happy with what I delivered, on average!

In retrospect, I realized I had not been writing focused on telling a great story so much as to explore a set of musical progressions, and tell a bit of a story too perhaps. This new approach really changed my thinking in huge ways - it was very story-centric. Music fundamentally as problem-solving! Music fundamentally as storytelling - even 15 second clips could tell a story. It seems an obviously necessary component looking back on it all. I’ve always been a big fan of musical theater as well, and so this brought all my perspectives together into one exciting musical singularity. I even started working on a musical theater project with a friend - which is still a work in progress!

These days I am passionate about writing what I call “semi-classical” music. I especially love writing for strings because of the harmonic interactions between violin, viola and especially cello & other instruments. These instruments are so emotive and compelling, they almost tell a story just in and of themselves via their respective tonalities! Basic cello arpeggios alone can make up an entire really compelling song if you’re careful about how you construct it.

A couple years ago, I started publishing & releasing music again under a made up band name - on Spotify & beyond as “Dream Optimist,” an iteration of a name that originally came from my decades-long love for the music of David Byrne/the Talking Heads, & the Talking Heads’ film, “True Stories” - as well as a chance (and somewhat embarrassing - a story for a different time) encounter in the early 2000’s when I met David Byrne & Tina Weymouth (both of the Talking Heads) outside of a restaurant in San Francisco. Under this project’s auspices, I’ve been putting out songs I call indie synth pop / chamber-pop / bedroom-pop - but the goal isn’t to stick to a genre, but to have a reason to finish producing songs. That is, there’s a goal-oriented quality to making music that gets me focused and working in a more precise way - versus just sitting at a piano and fiddling around, & then walking away & not thinking about it again.

To that end, I have a few sort of 70’s synth sci-fi sounding things I’m considering putting out next, as well as a few fairly classical-sounding things that might go after that. We’ll see. A friend recently told me he thought some of it sounded like the early work of famed (& brilliant) film composer Angelo Badalamenti; I should be so lucky! But I’ll take it.

To zoom out a little, getting a little philosophical - for me, writing and producing a song is a process sort of akin to taking an unhewn block of marble and figuring out what the statue hiding in the marble is, what the marble “wants” to be. As I hear it, each song wants to be something, and I feel like I’m working to help it become what it wants to be. The process is all about flow & imagination, and though I do get a voice evaluating how a given idea will be received by an outside audience - I can pretty well silence that voice by saying something like, “What outside audience?”

Of course, I would love to have people hearing the music I’m making - but it’s very freeing to not have feedback from anyone else so every song can be an exploration in making something I think is wonderful in some way, and that’s it. I’m the audience; in many ways, I like that. There’s an improvisatory and off-the-cuff quality that I sometimes can manage that makes me feel I’m really being there in the room at that moment - which is a lot of the point of what it’s always been about for me.

In terms of ways of being, it is a particularly great counterpoint to my work in Product Management, which is often all about analysis; careful measurement & consideration; careful sculpting of storytelling as I think about how ideas will be received both by customers and by stakeholders; and any number of processes that require specifically heavy intellectual work & reflection in order to be successful. I love that work too - but it’s a great counterpoint.

I mentioned earlier that I also studied a lot of music theory. I’ve heard a lot of musicians suggest studying music theory is specifically counter to the notion of what music is, which they often describe as a purely “feeling” art. While I agree it is about feeling, that’s not the sum of it. To my mind, every practice is about gaining knowledge of that practice, gaining muscle memory (whatever that may mean for that particular practice) relating to that practice, and then… practicing. But you have to have a basis for this practice - and you can and should be always learning, or else you’re standing still.

There is a great Charlie Parker quote relevant to this thought:

“Master your instrument, master the music & then forget all that & just play.”

I think about that a lot - you have to learn and aim for mastery. That takes study. And each new piece of music requires gaining mastery. On some level you’re never really “there,” never done gaining mastery, per se - there’s always new learning; but mastery alone isn’t the goal. What does mastery even mean? In my view, if you work hard enough to get to the point of being able to express yourself in a given domain or practice, and have fun with it - and that’s pretty good. Technical skill is hardly the be all, end all. The critical thing is to not be afraid to try something new, question your own assumptions, and to understand that these varied things we do cross-pollinate and make our lives broader & more meaningful.

Addendum: You can hear my recent work on Spotify here, and older work on this and this Soundcloud if curious for more.

· 4 min read
Yiyang Hibner

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How did you form the idea of starting Leland?

John: I’ve always been fascinated by the power that comes from connecting people to people. I saw it up close while building product at Uber, LinkedIn, and Curated (three people-centric marketplaces) and while building my own coaching business. These experiences ultimately led to insight into the expertise economy and the many new trends that were emerging. Once the idea for Leland hit, we knew we had to go after it.

How long did it take to actually hit the ground running?

John: Thankfully, the early team for Leland came together quickly. I called all the most talented people I knew and we got started. Zando and Jiashuo started building the product. Erika ran point on everything coach and customer. Andrew took on growth. I worked on product and pulled together our pre-seed round right around the time we launched, in July 2021. After that, we were off to the races.

What was your biggest fear before full-time committing to start-up life?

Erika: Right before joining Leland, I was working on my own e-commerce company that was growing quickly and had some cool opportunities ahead. When John called me to join the founding team, I had to decide if I'd keep building my online brand, or if I'd take the leap and go all in on Leland. After talking to John (and Zando), catching the vision was simple and my excitement was at an all time high. I felt I would always regret not working with them and building this company together.

So, I wouldn't say there was necessarily “fear” involved with the commitment, I just wanted to make sure I felt confident knowing I was leaving something good behind for something even more incredible. I am beyond sure that I made the right decision — I have never felt more bullish on the impact Leland will have.

What are some areas you are looking to improve as entrepreneurs?

Zando: Part of the fun of building a company is adapting to different needs as the company grows. We’re constantly looking for opportunities to develop ourselves and better serve the needs of the business, whether that’s building our industry knowledge/expertise, enhancing our leadership and management skills, or fine-tuning our communication within the team.

How do you divide tasks as co-founders?

Erika: As co-founders, we frequently discuss what our path forward is and the company strategy, goals, team, and execution plans we need to get there. We have great communication, so it feels natural to know what we need to own together versus what tasks we can divide and take on individually.

Zando does an incredible job running the engineering org and inspiring the team to build quickly and deliver high-quality outputs; our speed and focus is largely due to his influence. I run everything coach, customer, community, and employee — making sure we always provide a world-class experience. John is amazing at holding the whole team accountable, making sure each organization/workstream is prioritizing the right work, running product, and leading the overall direction of the company.

What are some of the biggest challenges you have been facing recently?

John: We’re very lucky to have two important things: (1) an excellent team, and (2) a big market/opportunity. Of course, every day comes with challenges, though. One of Leland’s biggest challenges is learning to build a product and a GTM engine that can support multiple coaching categories. We have coaches in everything from PM to medical school. Of course, there is a lot of overlap in some ways, but there are many differences as well. At first we operated in 1 category, now we have ~10 featured categories, but customers have purchased coaching in ~30 categories.

What does the future of Leland look like?

Zando: Bright! Our ability to both utilize and enable the expertise economy will grow as we expand, providing new opportunities for both sides of the marketplace. We’ll continue to develop and add to our core marketplace dynamics while layering in complementary offerings to address all the parts of helping our customers reach their goals. It won’t be long before Leland is the go-to destination for helping people achieve their career/education/outcome-driven goals.

If our readers want to learn more about Leland, what is your pitch?

We want to help you reach your most ambitious goals! Not only are our coaches are some of the most talented people in the world in their respective fields, they are also genuinely good people who try their best to go above and beyond to help the people they work with. No matter your budget, background, and goals, we’re here to help.

You can get started at or follow us on LinkedIn.

· 7 min read
Yiyang Hibner

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Guest post author: Yogi Sharma, PhD

Two days after deciding to leave a job that promised to pay over a million dollars a year, I woke up panicked and in sweats in the middle of the night. This is the first time I experienced a panic attack. I knew right there that I had made a blunder to decline such a seemingly great job and decide to “follow my passion”. I knew I was going crazy. In the moment, I could not see the thoughtfulness and discussions that had gone into making that decision.

Making hard decisions is hard. If our decisions go against the grain of what everyone else seems to be doing, that adds to sticking with it when we are not sure about its soundness.

Decisions are the bread and butter of a conscious living. In the intricate labyrinth of life, we stand at crossroads everytime we're faced with making decisions. This job or that job? Staying or quitting a job? Stick with the relationship or call it quits? And on and on.

And then, we have to deal with the outcomes of our decisions, of course. Outcomes are not deterministic. Just because you make a good decision does not mean a good outcome is guaranteed.

Good decisions vs. good outcomes

It's crucial to understand that our decisions are the choices we control, while outcomes often fall prey to unpredictable factors. This forms the peculiar paradox of decision making: sometimes, well-informed decisions lead to unfavorable outcomes, and vice versa. The key is not to judge your decision-making process solely based on the outcome, particularly when the aftermath is less than pleasant.

One approach to understanding this concept better is through a decision-outcome matrix:

  1. Good Process, Bad Outcome: You've followed a sound decision-making process, but the result isn't as expected. Consider this as a learning curve, a chance to persevere, and a test of your patience.

  2. Bad Process, Good Outcome: Your process was flawed, yet you landed on your feet. Don't be complacent here; ensure to change your process for the future before you forget that the outcome was caused by a bad decision.

  3. Bad Process, Bad Outcome: This is a call for introspection and a dire need for process correction. This is a good and cheap learning experience though, as you are less likely to be fooled by a bad decision just because it gave a good outcome.

  4. Good Process, Good Outcome: You've hit the bullseye! When you land here, aim to replicate your strategy.

Faith in the process, coupled with verification of its effectiveness, plays a critical role. This faith can be built from scientific data, others' experiences, your own past experiences, or even anecdotes.

Making right decision vs. making decision right

An essential aspect of decision-making is patience. We often rush to conclusions and expect immediate gratification. However, the unfolding of a decision and its outcomes takes time. A perfect example comes from renowned religious studies scholar Huston Smith and his experience with Vipassana, a form of mindfulness meditation (told in his book The World's Religions). When he arrived at the course, he wanted to study the effects of Vipassana on his consciousness and mind. And he was going to follow the scientific process to do that. The teacher told him to not analyze anything during the 10 days of the course, but rather collect data, as an objective observer during those 10 days. And then analyze, slice and dice in whatever way he wished after the course was over. That is the patience in action. Many times, we are impatient about analyzing our experiences, and that leads to less than sound decision making. Smith trusted the process and remained patient, meticulously noting his experiences and, over time, appreciating the benefits.

The decision-making process isn't solely about external considerations; it's equally about your internal state post-decision. Good decisions should make you feel light and empowered, while unfruitful ones may leave you feeling confused and heavy.

And that leads me to the story of leaving my job. I had thought about leaving my job for a while, and had analyzed various angles of it. I had found it to be a sound decision, but it was still hard to make the move. I found myself unsure and overwhelmed with the numbers and spreadsheets and pros and cons. And then the moment of clarity happened while I was sitting in a large conference room with wall-sized glass windows overlooking a beautiful garden and blue skies. Then, this question popped into my mind: "Would I do this if I had 5 years left in my life?" The answer was instantly clear, and it was a resounding 'no.' This query, a balance between long-term retirement plans and the often-used "what if today was your last day," provided the clarity I needed. I felt light, I felt empowered, and I felt ready to take the plunge.

This experience taught me that effective decision-making often hinges less on finding the right answers but more on discovering the right questions. Once the right question appears, the decision often makes itself.

When you find yourself at a crossroads next time, trust the process, find the right questions, and remember: you're not just making the right decision, you're also making the decision right. Decision making is just the starting point of living the decision with conviction and trust. This involves committing to your decision, refraining from second-guessing your choices (unless new data shows up, not just old thought recycling in our heads), and showing patience, perseverance, and tenacity.

When it comes to decisions and outcomes, consider them as leading and lagging metrics respectively. Leading metrics are the inputs that you can control, whereas lagging metrics pertain to outcomes, mostly out of your direct control. The crux of the matter lies in whether we are measuring the right leading metrics.

It's invariably easier to discuss the concept of sticking with a decision than to actually commit to it, especially when facing undesirable outcomes that cause fear or discomfort to arise. The natural response is to question our decisions, but one strategy I've found helpful to manage this doubt is borrowed from computer science. It's a concept called memoization used in dynamic programming.

Once you have figured something out, you want to write it down, and not do the expensive recomputation over and over again, every time your mind fancies contemplating it. When I decided to leave my lucrative corporate job mentioned in the opening, even though the decision was sound, thoughtful and had taken years to crystallize, it did not stop me from breaking into sweats at night and waking up anxious. My written reasons for making the decision was the only solace during that time… which I could easily access, instead of having to go through the years-long decision process again and try to convince my freaked out amygdala.

Another critical strategy to stick with a sound decision is introducing a pause between doubt about the decision and the decision to revoke it. Market downturns are classic examples of situations where many hastily doubt their carefully planned investment decisions and pull out before allowing for a pause between the doubt and action.

However, mastering the art of pausing is no easy task, particularly when experiencing emotional turmoil. Yet, habituating this skill is crucial in preventing us from hastily reversing a sound decision in moments of panic. This pause can be achieved through mindfulness, a process cultivated through formal practice that teaches us to observe our body sensations.

Enjoy the journey of decision-making, understanding it's not just about the destination, but the path you take to reach there.

In the days following my decision to quit, the panic attacks and anxiety turned to calm reflection on my long process that had led to this thoughtful decision. I went again and again to my written reasons to make the decision, which kept me calm and centered. I took regular pauses of mindfulness when the feelings were too strong. And after a few weeks, the confusion blossomed into a new way of life, where I was looking forward to a new career in the making.

· 4 min read
Yiyang Hibner

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Crystal Li:

Yoga has become an invaluable part of my life. It fuels my heart, making me feel deeply connected with myself. This practice is so rich and timeless and reminds me of the importance of self-care, self-awareness, and self-acceptance.

My yoga journey began over a decade ago. As I transitioned into the product manager role, I found myself navigating a new level of stress. Yoga came to my rescue, providing a sanctuary to unwind and release anxiety.

During the pandemic, I paused my practice, as I prefer to engage in yoga not in my home alone but in a studio, surrounded by a crowd of compassionate souls. Everyone is not there to judge but to collectively immerse in the gentle flow of yoga's mindful dance.

I restarted yoga recently during this particularly challenging period after being layoff. My yoga mat became my anchor, a space where I could temporarily let go of the external world and dive into the tranquility within. It has been like returning home after a long journey. Each pose, each stretch, and each breath feel like a welcoming embrace and help me find strength.

Choosing to embrace yoga as my hobby has been one of the best decisions I have ever made. My hope is that it becomes not just a pastime but a way of life. A saying often echoes in my mind: "You are as young as your spine is flexible."

Yiyang Hibner:

I love drawing - whether it’s doodling, random prompts, or following a tutorial to paint a flower from Youtube. Recently we are getting into a new routine in our family so I haven’t painted as much as I would like. I am a huge fan of systematic learning - where I can participate in a group class and learn together with others with guidance. In the past, I have attended a 10-week adult night painting class in Palo Alto, joined online iPad drawing class with other students in China, and completed another cohort-based kids/adult drawing class in an app. Drawing to me is an expression in art and you can do it anywhere anytime (even with just a pen and napkin!). Once I feel more settled in my new job, I hope to find set-aside time weekly to listen to relaxing music and follow a Youtube tutorial again.

Tanvi Shah:

As PMs, we use our brains so much that I find respite in physical activity pursuits like dancing, playing the piano, biking and strength training.

I have been a dancer since a young age. I trained in the Indian classical dance form of Bharatanatyam. This dance taught me patience, strength and expressions. Beyond that, I have dabbled in salsa, bollywood and a bit of hip hop (and realized I am terrible at hip hop). I still love dancing and have been relegated to playing dance off with my son. I hope to pick up dancing and learn a new dance form soon. Tell me which dance form I should try.

My son and I are currently learning the piano and it’s been amazing. I am flexing the left brain that rarely gets used. It’s made me appreciate music in a whole new way.

I ensure I bike/dance and strength train every week. Physical activity is an amazing escape. It makes me forget everything while ensuring that I have happy hormones. It has also reduced my stress. The struggle is taking the time out to do all these things.

Hanyu Gao:

I have a passion for creating, whether as a PM or as Creator - making something cool is what drives me. I make vlogs in my leisure time, edit via CapCut and Final Cut, and share on the WeChat Video platform. What pleasantly surprised me was the overwhelming support and appreciation I received from my friends, who thoroughly enjoyed my vlogs and told me they laughed a few, with data ranging from 800 to 6,000 views each video, and the top 10 posts over 1,000 views each. However, those videos are in Chinese. After recently relocating to the U.S. and expanding my social circle to include friends from diverse cultures, I felt inspired to create and share more clips in English. I thus made my new Youtube channel: @heylori. Feel welcome to have a look!