A mental model for choosing your next operating role

By Henry Su

In the summer of 2019, I packed my bags after spending 1 year in management consulting at McKinsey, moved to a new country, and joined a 60-person startup working to build autonomous semi-trucks. While this path is fairly accepted in Silicon Valley , it was anything but normal coming from a midwestern Canadian city. I distinctly remember a former colleague asking me unabashedly: “What on earth are you thinking?”. Feeling almost ashamed, I muttered something about how I thought self-driving technology was the future. What I wanted to tell him is what I’ll share with you now: my mental model for choosing a meaningful operating role.

Taking off the Advisor hat

First, let’s explore my decision to leave consulting. I believe the two most compelling reasons to leave a job are:

  1. Your growth plateaus.

  2. Your impact isn’t obvious.

My reason was the latter. As an individual contributor in a massive firm, my impact was muted by my limited latitude to make decisions. As an advisor to clients instead of an operator, I was restricted from execution, where real impact is felt. I vividly remember a consulting engagement in which we spent weeks on workflow reviews, staff interviews, and powerpoint deck iteration—only to see the whole project axed because a C-Suite client who was less-than-fond of consultants finally got his way. I left that project feeling like my work was meaningless.

Parallels between consulting and startups

Why join a startup? One reason was so I could leverage my existing skillset. I saw a lot of parallels between consulting and startup business generalist roles. Consultants are trained to:

  • Provide structured problem solving approaches to ambiguous challenges.

  • Deliver recommendations in environments with constant context switching.

  • Serve people of all layers in client organizations.

This skillset is high leverage for startup business generalist roles because:

  • Early startup practices are often unscalable (you may interact directly with your first few users). As the startup scales, there is a growing need for repeatable processes and structured frameworks for problem solving.

  • Roles aren’t neatly delineated. As a business generalist, you’re often moving between building, selling, recruiting, etc.

  • Company structures are generally flat enough that you get to work with people across the entire organization.

In a business generalist role at a startup, a consultant can create value by developing playbooks to help the company scale, seamlessly switching between different functional responsibilities, and acting as the connective tissue to solve problems across the organization.

Objective value and subjective fulfillment

A deeper reason for wanting to join a startup was my desire to be in a meaningful role. I believe the degree to which a role is meaningful is calibrated across two dimensions:

  1. The extent to which the role creates objective value for the world.

  2. The extent to which the role elicits subjective feelings of fulfillment.

The objective value or impact of a role is a combination of:

  • The role’s impact on the organization.

  • The organization’s impact on society.

The subjective feeling of fulfilment can be elicited by:

  • A mission that is personally inspiring.

  • Professional growth and development.

Empowerment to make an impact

The first element to a meaningful role is the extent to which it creates objective value for the world. Startups arguably provide the most empowering environment for individual impact. Their flat organizational structures enable decision making responsibilities at the individual contributor level. Further, employees are encouraged to act entrepreneurially given the pace at which startups move.

I took on a Chief of Staff role at Embark Trucks, a company building self-driving semi-trucks. This particular business generalist role serves as a force multiplier to the CEO and leads the implementation of new processes to ensure the organization scales smoothly. I felt this role positioned me to make a lasting individual impact given it’s latitude to shape the organization.

In thinking about whether an organization could change society, I invented a framework that I’ll refer to as the ‘time machine test’:

If I were to take a time machine and travel 5, 10, or 20 years into the future, are there elements of society that might be manifestly different, in a good way?

Can the organization under consideration help shape one of those future elements? The sharing economy, meat substitutes, and autonomous vehicles are all phenomena that pass the ‘time machine test’.

In my specific case, I fervently believe self-driving will be one of the most important paradigm shifts in transportation and the broader economy this century—and Embark Trucks has a shot at being a contributing player.

Finding fulfillment

The second element to a meaningful role is the extent to which it makes me feel fulfilled. I believe fulfillment can be drawn from two properties of work. The first property is the extent to which the work aligns with my personal mission or passions in life - how much the work resonates with my core values and personal interests. The second property is the extent to which the work enables my professional growth by building my skills and network. This property is valuable because it equips me with the resources I need to later pursue work aligned to my personal mission. I believe the perfect role is rich in both properties - it enables professional growth and serves a mission I care about.

Robotics has always been an area of deep interest for me—when I was 13, I joined a competitive robotics team that went on to win a world championship in its first year. For me, working in self-driving combined the allure of engaging in an intellectual hobby with the promise of delivering profound social, environmental, and economic impact. Hence, I felt I was joining an organization with a mission I was passionate about. Further, I was joining in a role that operates closely in tandem with the CEO and executive team, providing a unique opportunity to learn from experienced business leaders.

Places to look

Everyone has a different interpretation of what makes a role meaningful. I will share some examples that fit my personal mental model. The following contexts can offer meaningful opportunities:

  • Earlier stage startups - Individual contributors have more decision making responsibilities given flat organizational structures. The pace of change creates an evergreen roster of opportunities.

  • New product or service line - Regardless of company size, the creation of a business unit to manage a new product or service line heralds an opportunity to grow an organization from the ground up.

  • New geography - The expansion of a business into a new geography creates opportunities to build new teams, processes, and infrastructure.

From a role perspective, the following types of business generalist jobs can provide a meaningful experience:

  • Chief of Staff (CoS) - In larger organizations, the CoS acts as a confidante, gatekeeper, and right hand to an executive (often the CEO). In smaller organizations, the CoS can own ‘everything’ non-technical including branding, marketing, business development, product, etc. In either case, CoS roles demand a versatile toolkit of skills and have the seniority to influence strategic business decisions.

  • Special Projects - Special Projects roles often tackle a variety of high priority strategic projects. These could include building new teams/functions, growth planning, partnerships, fundraising, etc. Special Projects positions can be fulfilling as they are plugged into important company initiatives and are inherently results-oriented.

  • BizOps - BizOps roles often act as ‘COO’ to a product or vertical, providing operational and strategic support. These roles can be meaningful given the broad array of project exposure and high degree of responsibility and autonomy.

Parting thoughts

Many people who work in client services inevitably face the question of: Where next? I believe the next role should be chosen based on how much objective value and personal fulfillment potential there is. My interpretation of this model led me to consider a variety of business generalist roles in high growth environments that enable personal impact and professional development. Ultimately, I hope this mental model can inspire you to find a role that is truly right and meaningful for you.

Empowering talent networks to diligence their next opportunity

Empowering talent networks to diligence their next opportunity

"For folks in school/other roles looking to break into PMing: write a strategy memo for a company you want to be PM at and publish it online ( tweet/post). I’ll bet you that it will get you a serious conversation with their product leads… Biggest key: showing you understand the “system” as Keith Rabois calls it" - Sriram Krishnan

We, at Renaissance Collective, saw this tweet, thought it was pretty sage advice, and were inspired enough to try a small experiment. Could we, as a group, help each other write memos that would contribute to our collective understanding of the company and the system within which it operates?

Some context: As a community of smart operators, we’re helping each other navigate new professional opportunities. We have been thinking a lot about information asymmetries in the startup ecosystem. Information flows through tight founder networks (e.g. YC), investors routinely share diligence on companies, but there’s no community for operators to share information on companies, roles, or compensation. Moreover, investors have carefully structured processes around evaluating companies before they make a commitment -- yet investors get to make a portfolio of bets so the risk is shared across their portfolio.

As an operator joining a company, you only get to make a single investment – that of your time. In this situation, it’s even more critical to do great due diligence. Yet operators lack structured information networks or rigorous processes to evaluate opportunities.

One of the exciting things that we see happening in Renaissance Collective is that our members have been helping each other with diligence on companies. This happens daily on our Slack channel with questions like, "Does anyone know anything about this company?" or "Here's an interesting article about this company that just raised $X -- what do you guys think?" While this lightweight information sharing is helpful and generates interesting discussions, we're also trying to do more to create a community-generated, collectively empowering process around diligence, so we can help each other evaluate new opportunities.

One of our members, Gavin Zhang, wrote a memo this week to formulate a view on whether Hims, the D2C men’s wellness brand selling erectile dysfunction and hair loss meds, will be successful.


Gavin presents a deep dive into understanding the system in which Hims is operating, including a look at:

  • How Hims’ marketing takes advantage of changing public perceptions of masculinity and the growing popularity of ‘wellness’ products as consumers strive to take ownership of their health

  • The competitive landscape and critical levers of operational efficiency for D2C distribution

  • Regulatory risks and the implications of a policy crackdown on d2c drugs and telemedicine platforms

He structured his memo by presenting:

  • Basic facts about the company and business

  • Reasons why he believes Hims faces an uphill battle to maintain its impressive growth trajectory

  • Ideas on how Hims can maintain an edge over its competition

I won’t spoil the conclusions for you. Check out Gavin’s entire memo here. Even if you’ve already made up your mind on Hims, Gavin's piece is worth a read for the insights he offers on the potential risks that all D2C companies face.

One happy side effect of writing such a memo might be that it garners the attention of product leads at your dream company, as Sriram writes.

However, within the context of Renaissance Collective, we as a community, contributed to Gavin’s thinking on this memo, as part of a process of helping him do diligence on Hims. In the process of writing this memo, Gavin formulated a view on what he believes are the risks associated with any opportunity at the company. This memo will live in our ‘company dossiers’ which are member-generated and shared across the community. It’s a small part of our effort to equip talented operators with the best possible tools for evaluating the most valuable investment of their time.

If you have any thoughts on how we can iterate and improve this process, we would love to hear from you. And if you’d like to participate in our collaborative process on empowering talent networks, join us by applying here.

Hims is an Uneasy Bet. Here’s What it Needs to Do to Win.

By Gavin Zhang

Hims’ recent entry into the unicorn club is unexpected. I was intrigued when I read that Forerunner, Redpoint, and Founders Fund all contributed to the company’s recent $100M series C. Who knew that selling prescription generic Viagra direct-to-consumer could garner a $1B valuation within 2 years of existence? In this memo, I argue that following its early successes, Hims will need to double-down on operational efficiency to offer customers speed and convenience, while defending itself from competition. To win, it will need to improve its customer experience, expand into physical stores, and build a team of  medical-policy experts to navigate an increasingly complex regulatory landscape. 

Here are the basic facts about the company:

  1. The Pitch: Hims and Hers empowers men and women to take control of their wellness and health on stigmatized conditions like ED, balding, and birth control by buying products like generic Viagra, hair loss medication, and birth control pills discreetly.

  2. The Business Model: Customers pay for subscriptions starting at $20/ mo membership fee for access to the platform and physician network. To purchase products, customers fill out questionnaires and consult with a licensed doctor via email or phone to obtain prescriptions. They receive their prescription in about a week’s turnaround time. The company partners with Bailey Health for its network of doctors who prescribe and interface with customers and Truepill to help fulfill its orders.

  3. Price Breakdown: According to the site, Hims sells generic Viagra at $30 for 10 pills or $3/pill. Romans, their main competitor, sells 10 pills for $20 for or $2/pill. According to GoodRx, a person can obtain generic ED meds with a coupon at $12 for 30 pills or $0.40/pill.

  4. Fulfillment Speed: Hims delivers most products to the customer in 5-7 days of standard shipping. Romans delivers its products in 2 days.

  5. Growth Trajectory: Hims launched in 2017. In its first week, it earned one million dollars in revenue which, the founder Andrew Dudum says, was its weakest week of sales. The company has declined to release any other revenue numbers, but it has grown at an impressive pace. In little over a year of existence, it has also launched Hers, a new product line targeting females.

The early growth has been impressive, but I’m a bit skeptical about how Hims can sustain its success. It’s an uphill battle for Hims for the following reasons:

1.Hims is selling a commodity product: 

Hims sells generic Viagra for ED and hair loss supplements for men and birth control for women, as well as vitamin supplements and skincare for both genders. The packaging looks really impressive with its sans serif font, but at the end of the day, there is little they can do to make their product fundamentally different than what their competitors or existing incumbents are selling. Because of an inability to differentiate on product, Hims will have to win customers on marketing, customer experience, price, and convenience.

2. The main lever for differentiation is marketing, which doesn’t seem sustainable:

The only way Hims can differentiate its commodity product is through marketing. Its eye-catching, clever subway ads (the infamous cactus), generate conversation over stigmatized medical issues like ED, baldness, or bad skin. Gin Lane, the branding agency that partnered with Hims, created a brand strategy that was at once deeply empathetic and casually conversational. With punchy copy and a tongue-in-cheek approach to sensitive issues, Hims urges its customers to embrace, “Prevention,” as “more effective than denial,” Hims has hit the zeitgeist amongst its target millennial audience with topics that feel even more pertinent as masculinity norms are changing. The problem will be whether marketing is sustainable as a differentiation strategy in the long-term.

Hims’ early successes in marketing a commodity product are reminiscent of Dollar Shave Club’s story. With a simple subscription model of $1/mo and an insanely viral video that kickstarted its brand awareness in customers’ minds, Dollar Shave Club reached 20 million people. The ad, in combination with sharp social media marketing and engagement, converted viewers to customers who, in turn became brand evangelists. P&G, on the other hand, had to pay billions for TV (2018 big pharma ad spend for TV alone was $3.7B) to convince customers to buy Gillette to look like Roger Federer. 

Dollar Shave Club was able to win and convert a lot of customers with emotionally resonant marketing. The problem was that it needed to keep spending money in an increasingly competitive online ads market to acquire new customers. One could argue that this led to its $1B eventual exit via Unilever, as it couldn’t find a way to scale ad spend profitably.

Hims has emotionally resonant marketing but it's an uphill battle to find a way to scale while managing its CAC in the long-term. Furthermore, its competitors will face the same battle, meaning that these brands will also have to compete on ad spend.

3. Big name brand pharmaceuticals are losing their patents and there’s more competition for generics: 

As Pfizer’s patent on Viagra and Lipitor are expiring, the barriers to entry for these particular product categories are lower for new players. We’ve already seen a spate of new startups pop up to offer these products: Romans (directly competitive with Hims and also founded in 2017), Nurx (birth control), Cove (migraines), Zero (quitting smoking), and Lemonaid (all of the above). On the incumbent side - Pfizer is mobilizing to consolidate off-patent divisions like Upjohn and Mylan to help leverage its scale to control more of the market on its generic drugs. Furthermore, Wal-mart and Amazon have all launched telemedicine apps which ultimately delivers pharmaceuticals  -- and these are two of the most operationally efficient companies in history. Between huge incumbents and smaller startups, Hims will have compete on operational efficacy.

4. Looming regulatory risk: Washington is going to start looking into how D2C platforms enable communication between doctors and patients:

Due to a recent rise of bad actors, the core mechanism of how consumers and doctors communicate via D2C platforms is going to come under increasing regulatory scrutiny. For example, there’s been a rise of scams that target the elderly for braces. Currently, Hims is only dealing with low-risk medical conditions, so an easy checkbox questionnaire for customers to gain access to generic ED pills seems sufficient. However, according to some health advocates, Hims’ methods of prescribing drugs do not even meet standard AUA regulations. It’s reasonable to expect Hims and similar competitors will come under more scrutiny as regulators crack down on how doctors and patients communicate to obtain prescriptions.

The casual style of marketing is also under fire for advertising beta-blocker propranolol, an FDA-approved treatment for hypertension, as a cure for per­­formance anxiety. The casual tone of marketing the particular product as a “wellness” product worries many health advocates that customers are only being sold the benefits of drugs without proper warning of the risks. 

All of these examples point to an impending regulatory storm for D2C platforms. If stricter regulations are imposed, the casual and provocative marketing that was crucial to Hims’ initial successes, may be at risk.

If Hims is facing an uphill battle due to previously listed reasons, it’s also important to note, so are all of its competitors. As a customer, I would stick with Hims if they’re delivering on the promise of convenience, great customer support, and low prices.

 

Here’s what I think Hims needs to do to win:

1. Improve its customer experience, starting with transparent communication around pricing:

In a hyper-competitive environment, Hims only has one chance to win customers on a good experience. It needs to be proactive in explaining their billing process so the customers know exactly why they’re getting charged. Any confusion will lead to a bad experience. I took a look at customer reviews on Trustpilot, a third-party site for customers to post verified reviews. Hims has a  “Great” rating or avg 4/ 5 stars based on 317 reviews with customers.

Here’s a screengrab of their customer reviews on Trustpilot, which offers a ratings break down:

Screen Shot 2019-11-03 at 5.16.44 PM.png

The most interesting fact that stands out is 12% of their reviews are “Bad,” which is the 2nd highest proportion of their reviews. That’s a sizable portion of their customers that really disliked something about their experience and I sense there’s a repeat issue that is causing such a sizable negative response. 

After digging in, the consistent call out from these 1-star review customers is that they failed to receive product but still got charged.

Screen Shot 2019-11-03 at 5.16.53 PM.png

The website explains that customers’ orders are fulfilled with 3 refills at once, and are charged per refill per month. I suggest that they either charge customers upfront for the 3 refills in one lump sum and explain the breakdown or keep the existing billing process but explain more clearly to how the customer will get charged. Right now, there’s nothing on their website that discusses the billing process clearly. As a result, customers think they are getting scammed.

2. Expand its physical presence and offline distribution:

Currently, Hims partners with a 3rd party pharmaceutical distributor like Truepill to help fulfill customer orders. This is money they could be reinvesting in their own supply chain. Hims is already building out its first brick-and-mortar location in Columbus, Ohio. This physical location will handle some regional fulfillment via mail orders. While one could argue Hims’ sales dollars are better funneled into ad spend for customer acquisition, I think Hims should invest in more physical locations for 4 reasons:

  1. A physical location is a distribution point that can help speed up fulfillment which is important for winning over the consumer.

  2. Consumers are increasingly channel-agnostic. For example, a customer may want to have the option to go to the store to try on a dress only to order it online. I’d imagine it’s going to be similar to prescription fulfillment. I want the flexibility to receive my order in the mail or pick it up in-store, depending on whichever option is the fastest.

  3. A physical pharmacy with a pharmacist on hand can answer customers directly. While a brick and mortar pharmacy may lose some points on satisfying a customer's desire to be discreet, having a friendly in-house pharmacist on staff to address potential questions and patient concerns further advances the brand's desire to be perceived as conversational and approachable.

  4. A physical space helps contextualize customer data. Hims can learn a lot about its customers’ raw data via online transactions, but having physical spaces can give HIms more localized market data on customer behavior. This creates a feedback loop that can generate potentially interesting insights for future platform product innovations about customer experience. 

 3. Build out a team of policy-savvy medical professionals

Hims recently recruited Pat Carroll as their Chief Medical Officer. He served Walgreens as Chief Medical Officer for 5 years. This is a strong move from Hims because they are already aware of the impending regulatory risk, and an experienced executive can navigate the murky waters of Washington for the brand. The company needs a specific health-policy oriented team to protect their brand. 

Despite its meteoric growth, Hims is slated to face an uphill battle because of its undifferentiated product, reliance on heavy ad spend, a large number of competitors, and impending regulation risk. Nonetheless, Hims' emotionally resonant storytelling and entry into brick-and-mortar distribution could give it a sustainable edge over its competition. I’m going to be watching the company closely as it grows. I can’t wait to see how the service navigates 2020 and beyond.


The most valuable part of being a member in the Renaissance Collective community is that you're surrounding yourself with smart people who will challenge your assumptions and reasoning and help guide you to higher-level insights. Thanks to RenCo community advisers and members Jen Yip, Henry Su, David King, and Emily Hughes for reading drafts and helping me refine my thoughts. - Gavin Zhang

Bringing great people together since 1994

I’m often told that I’m a natural community builder and that one of my “superpowers” is bringing great people together. My affinity for assembling people started in high school with a community service club called SMILE (Students Making Improvements in Lives Everywhere). I started this community and helped hundreds of students see all the ways they could give back to their own communities -- ranging from bringing shelter dogs to visit the elderly, to tutoring children who lived in housing projects on the northside of Pittsburgh, to preparing meals at soup kitchens on the weekends.

For the past couple of years, I’ve organized a curated community of founders, researchers, professors, and engineers in robotics and AI for knowledge sharing among experts and practitioners. This community has created many new friendships, helped several of the members navigate career transitions, and catalyzed valuable professional partnerships across companies.

Separately, I recently launched Renaissance Collective, a community for smart generalists looking to explore careers in startups.

As a result of all this activity, friends often come to me for advice on how to build new communities.

While I don’t have any secrets to share on the topic, I think what’s become reflexive and obvious to me may not be as intuitive to others. Here’s my top advice on building community, in order of importance:

  1. Figure out how to serve people. If you want to build a community, this is the number one thing you should focus on. Why should this community exist? Ask yourself: what is your driving motivation for starting this community? Does it start with your needs as the organizer? It shouldn’t. The best communities come together because people have a compelling reason to spend time with each other. This may seem obvious, but I’ve seen how often people get the starting point wrong. Are you looking to build community as a marketing channel for your product? Are you looking to bring entrepreneurs together to increase your deal flow? These aren’t great starting points for building strong communities. Have a hypothesis about what potential users of your product or entrepreneurs find challenging today and what they need. How do you make their work more delightful, less stressful, and more productive? What processes or events can you set up to serve them?  How can you support people by building relationships and facilitating intros that will be valuable to them? People can tell if they’re being sold to or if you’re genuinely trying to create value. Do the latter. As a side effect, you may end up in the flow of lots of information and activity because you’ve assembled the attention of relevant people -- but people only become active participants and fierce advocates of a community because they appreciate the value you’ve created for them. Build a community you would like to be a member of.

  2. Curate members. People join communities that they’re proud to be associated with. Open meetups are a free-for-all and attract the lowest common denominator. This style of inclusivity isn’t conducive to creating strong communities. As the organizer of community, the most important thing you can do is invest a lot of time into figuring out why certain people should meet. This is the glue that binds your community together. You should get to know people on more than a superficial level, so you understand what they value, the challenges they face, and what they’re looking to get out of the community. Curate a group of people who share a common set of interests, problems, experiences, or purpose. Does this sound like a really high bar? It is. My recommendation is to start small. You’re off to a great start if you have half a dozen hand-picked people in a community and everyone has a compelling reason to meet each other.

  3. Set (and enforce) the guard rails that maintain quality. Now that you’ve curated great people, be explicit in communicating the purpose of the community. Set clear expectations for participation, acceptable behavior, and interactions. Whenever I host a robotics and AI event, I state the purpose of the community for all new members at the beginning of each event. I also reiterate the ground rules (e.g. “this is off the record, no blogging, no tweeting, etc. to encourage open discussion”). In Renaissance Collective, we have written community guidelines and shared values that are communicated as a part of our onboarding process. Setting high standards and expectations for the community enables high quality interactions. I’m often asked by people to share information with our communities, or even worse, I’m asked to share the emails of our community members.  To be clear on this: I will never email our communities with information that isn’t highly relevant or valuable to them, and I will never share personal information that we’ve been entrusted with. If you share the emails of your members without permission or you let people spam each other, your best people will leave. It’s your job to set and enforce standards for respectful communication. This is at the crux of facilitating the highest quality, mutually beneficial connections.

People are at the core of community. The spirit of community is generosity and service. So often in Silicon Valley, I see people create me-focused communities, or conflate community building with inviting folks to a fancy venue to share an expensive meal. I’m not opposed to fancy venues or great food, but the most significant investment you can make in building a community shouldn’t be the resources you pour into finding the perfect space or a Michelin-star chef. It should be the time you spend getting to know people so you can serve their needs better. 

As we grow Renaissance Collective, I am always excited to learn more about the things that have worked for you in building strong communities. If you have lessons of your own to share, or if you fundamentally disagree with what I’ve said here, I would love to hear from you!

PS We had our most recent Renaissance Collective bonfire at Ocean Beach with Chipotle burritos (pic above of the crew who showed up early to get the fire started). It was a really memorable evening for the dozens of people who attended. Thank you to Chipotle for the easy catering and to Karl the Fog for frequenting other haunts that evening! And as always, I am grateful to be a part of this community.


It’s not about my needs, it's about yours

By Ryan Rodenbaugh

Coming from Arizona State, I initially found it difficult to get the attention of technology companies and venture firms in Silicon Valley. Early in my career, the biggest mistake I made was framing things in a ‘me-centric’ way versus digging into what companies need and framing my communications in terms of how I would add value. This is the difference between writing a cover letter that says “I would like this role because I’ve done X” instead of saying, “I will add value to your company by doing X”. 

Whenever I’ve taken the latter approach of clearly stating how I’ll add value, I’ve found that I’m much more likely to get an enthusiastic response.

Also, in the process of thinking through the ways I’m able to contribute, I’m better able to vet opportunities that play to my strengths. 

As an undergrad, I knew I wanted to explore a career in tech. I left an internship at a public company in Arizona where I already had a full-time offer, to take a lesser paying job working remotely for a market research firm in San Francisco. It was clear that San Francisco was the best place to build a career in tech. A few months into the role, I attended an industry conference in SF. To prep for the event, I put together a list of all the attendees I wanted to meet. At the top of my list was a Managing Director of a prominent venture firm. I researched a bunch of his prior investments and knew exactly what I wanted to talk to him about. However, when he arrived, he was immediately swarmed by people and ushered onto the stage. He left right after his talk. I quickly skimmed the attendee list again to see if any of his colleagues were at the event. As luck would have it, an EIR from his firm (I’ll call her “MG”) was also there. I managed to grab a seat next to her in the crowd and have a brief conversation with her in between presentations. Since I’d already done extensive research on the firm’s investments, I was able to highlight my own (somewhat limited!) experiences in tech -- a senior thesis on IoT in cities, an honors paper on the impact of machine learning on financial markets, and personal research on crypto and blockchain -- as experiences that would be directly relevant to her and the firms’ interests. This gave MG confidence that I could provide value on some of her projects. After working with her on a few small projects, she gave me more responsibility and brought me onto larger projects. Eventually, she offered me a full-time role working with her in SF. This was the beginning of my career in tech!

When I applied for my next role, I emailed the CEO twice with what was, in retrospect, very me-centric emails that focused on my interest in crypto. I received no response. So I returned to figuring out how I could create value for him and his company. My former boss was hosting a dinner for entrepreneurs, investors, and thought leaders in crypto and I made sure that she invited the CEO of the company I was interested in, knowing that he would benefit from the network of people at the event. The CEO attended the dinner and I had a chance to follow up with him there. Even then, he still wasn’t sure if I was a fit for the role. The other candidate he was interviewing for the same role had 8 years of experience and a couple of Ivy League degrees whereas I had less than one year of work experience at that point. To give him more confidence in my abilities, I proposed that we work together on a project that I knew would be high leverage for the company. I spent a week on a ‘work trial’ (IMO, a highly underrated way for companies to vet qualified candidates!). By the end of my trial week, one of the co-founders told me that I was a unanimous ‘yes’ across the company. 

From all of these experiences, the key takeaway for me is that the best way to find new opportunities for yourself is to figure out how to create value for people. 

To summarize:

  • Avoid emails to founders/companies that are ‘me-centric’ and focus on the value that you can create for the company.

  • Research the issues and problems that are important to an org and frame your knowledge and experience as directly relevant. 

  • Send people events, news articles, tweets, etc. that you know will be of interest to them. This creates a touchpoint that keeps you top of mind. It also shows that you’re genuinely interested in their business and you understand what they care about.

  • Propose work trials where you’ll deliver on projects that are valuable to the org. This is a clear value-add and gives you the opportunity to figure out whether you work well together.

If you’d like to connect with Ryan and other smart generalists who are navigating their career journeys, you can apply to join Renaissance Collective here. And if you know someone who would benefit from this community, feel free to share this post with them.

Institutionalizing Luck

One of the ideas I’ve been pondering over recently is the role of luck in our professional lives. By this, I mean the random encounters or relationships that end up changing the course of our careers. I recently had the opportunity to attend the Operator Summit, a day-long meeting of CEOs and COOs. What struck me was how often the very influential speakers on stage would credit a single person for having taken a chance on them, as creating a transformative moment in their careers. Claire Hughes Johnson, COO of Stripe, for example, talked about how her business school classmate referred her into Google when she arrived in California after managing an unsuccessful political campaign (I share a few other lessons from the Operator Summit here).

If you think back on your work history, how often did the best opportunities come to you through a friend, colleague, or fellow alum? I got my job at the World Bank through a college alum, got introduced to my consulting firm in DC through a friendly neighbor, landed my first project in tech through a friend from grad school, and got my last job, as the first business hire of a startup, through our wedding officiant. The most interesting opportunities aren’t the ones you find posted on a public website – they flow through people networks.

For many of us though, making new connections that lead to these fortuitous opportunities becomes less of a priority. We juggle more responsibilities at work and home, and as a result, the time we dedicate to cultivating new relationships dwindles. However, in keeping our social and professional circles tight, we decrease our exposure to serendipity.

In the past month, members and companies in the Renaissance Collective have made dozens of valuable new connections for each other. We’ve become a meeting point for people who have common interests -- in autonomous vehicles, micromobility, and seed stage investing. Members have extended their personal and professional networks to other members and shared events that they’ve curated and vetted with the community.

Seeing all of this happen organically has made me confident that the Renaissance Collective community can be a conduit for institutionalizing the luck we’ve all experienced in one form or another. Instead of hoping you’ll bump into someone who ends up being a mentor, future coworker, or investor, you can do more to open yourself up to luck. You can invite it in by accelerating the frequency in which you meet great people.

The vision of the Renaissance Collective is crystallizing as we focus on creating value for the folks in our community. So much of the “oh you should really meet so-and-so” connections happen in our heads because we humans are really good at making less-structured, more ambiguous relationship connections. However, as we go about our daily lives, it’s not top-of-mind for us to think about ways we can be helpful by making mutually beneficial connections. Having a community where connecting the dots between people is the norm, generates a flywheel of network-extending interactions that surfaces the most interesting opportunities.

If you know someone who would benefit from this community of ambitious, smart generalists, feel free to share this post with them. I’m also happy to take personal email introductions to answer any questions.

Grateful to be a part of this community!

Jen