After joining Cherubic, I dove head first into connecting with our existing portfolio and taking meetings with prospective founders. When I look back at my notes and memos from my first year, I see this abundance of caution in my writing – “what if Google builds this, what if Amazon enters the market” I would note. Having just left Google, perhaps it was reasonable to be fearful that with a flip of a switch, Google would put a startup out of business. And frankly, in many cases they have. But in more cases, they haven’t. There are dozens of billion dollar ideas within Google. There always will be.

It took me a while to realize that in venture it’s easy to say no. Looking at all the things that are likely to go wrong is, well…obvious. And for a cautious person like myself, I was particularly good at identifying future risks. Perhaps unproductively good, because venture as we know is about the slim chance of outsmarting those risks. And this is where I’ve learned the most from Matt. His relentless optimism helped clarify for me the most important question in venture to ask:

 What happens, if everything goes right? 

Put differently – what would happen in the world if against all odds, an idea hits every tailwind, and manages to avoid every existential roadblock? This is my favorite thought experiment. It’s a framework I use regularly when talking to new founders to help me size the potential of an idea. It’s a framework I use regularly when talking to our existing founders to help them think through what strategic bets to take with their product. And it’s a framework I use personally when thinking about ways I can make positive change in our world that otherwise feels too daunting to try or likely to be impactful. Warning, this framework will lead you to make some foolish decisions! But that’s ok. You don’t always have to be right. At the core of this question is a fundamental orientation around optimism. And to be oriented around optimism is to see potential where others don’t. Matt showed me this from day 1. It’s his optimism that makes him so gifted and successful. And in recent years, keeping optimism at the center of my decision making has been a really beautiful thing. I wish for you and everyone in 2024, a foolishly optimistic year. 

1. Casual networking. It’s ok to say no. No to meetings with graduates from your college looking to break into your field. No to meetings with colleagues from your previous company. No to industry events, happy hours and conferences that you’ve been invited to attend or even speak at.
   
2. Investor & LP meetings. It’s ok to say no. No to meetings with your existing investors, potential future investors, or LPs visiting from out of town. If you are not in the headspace to fundraise or have confidence a meeting with an investor/LP will yield an investment, you can say no. 
   
3. Recurring 1:1s and meetings. It’s ok to say no. Your team needs you – but not proportionally. Not everyone on your team needs to meet with you weekly. You have permission to skip any and all recurring meetings that don’t give you energy, or drive your bottom line (frankly, those meetings should be canceled). Do not “sprinkle” your time evenly across the company to be seen as equitable. Disportionately say yes to people that make things happen.  
   
4. Internal projects. It’s ok to say no. No to an idea your team is excited about. No to a project that has already started and would be painful to stop. This is not just about saying no to protect your sanity, but to protect your company. Your team may be disappointed you say no, but they’ll appreciate the clarity that no provides. Saying no keeps the entire company focused on what you say yes to. You inform how your team allocates their time – not the other way around. 
   
5. Customers and existing clients. It’s ok to say no. No to loyal clients who have been with you since day 1. No to big brands who dangle their logo but have feature requests that aren’t on your roadmap. No to paying customers who drain your team’s resources. No to prospects who continually ask for demos and meetings that have yet to convert. Protect and insulate your team by giving them permission to say no to someone they feel they should say yes to. 

It’s counterintuitive to say no to the 5 invitations above. Yes is polite. Yes is likable. Yes is fun. Saying yes can also open doors to new partnerships, investments, and customers. So it’s worth clarifying that it’s ok to say no today and yes later.  Saying no today, however, isn’t being rude, selfish or overly transactional. Say no, so you can eventually say yes. Set tight boundaries today so you can eventually open them up. Not every invitation is made equal. Be discerning with your time, resources and energy – and sometimes the easiest way to do so, is to simply say no.

Later in my career, I joined Google where I built and led new business sales teams in the US and LATAM. I interviewed, hired and trained hunters for years. We weren’t farming in existing books of business or nurturing legacy relationships. We hunted for net new logos/customers ready to spend 6 figures on our ad platform. It wasn’t broadcast, but it wasn’t a walk in the park either. 

After eng, sales is likely your next hiring category. Flexport’s first hire, Anthony Chen, told me recently “sales solves all problems.” For the most part, I agree. What good is your product if nobody is using it? Sales is a critical early hire that you’ll likely get wrong at some point. Interviewing effectively, designing compensation correctly, tracking the right metrics etc all contribute to the success of your sales hires. But it ultimately starts with the interview – your screening process. Below are the top 5 qualities in sales people I optimized for when I was a hiring manager:

• Resilient
• Even Keeled
• Disciplined 
• Discerning 
• Storytellers

Let’s dive into each with a sample interview question to help reveal these traits.

Resilient

A good salesperson is not discouraged when they hear “no” from a prospect. They manage rejection well, and are tolerant of change (territory, commission, support structure, resources etc…). This is especially important for startup sales hires as the product, ICP, and competitive landscape are likely to evolve without notice. 

• Tell me about your best and worst sales quarter. What was the outcome? What actions did you take that led you to that success/failure? Looking back, what would you have done differently to have been more successful? What was your key take-away?

Even Keeled

Alternatively, a good salesperson is not overly excited when things go right. They have a healthy dose of skepticism with their pipeline, discount their projections conservatively and always work the top of the funnel (ie cold call new leads) even when they’re feeling confident about later stage deals. 

• Tell me about a time when you missed quota – why did you miss and how would you have done that quarter over again knowing what you know now (people who are self aware, even keeled, and proactive will not blame their circumstances – like the product or market – and will be metrics focused to know how to course correct). 

Disciplined 

Outreach is important, but without follow up, it goes to waste. The best salespeople know how to balance their pipeline with new daily outreach, and timely client follow up. Balanced momentum across the pipeline – not just at the top or bottom – is critical. 

• What metrics tell you you’re on track to hit your targets? How do you use them in your day to day? 

Discerning  

Not everyone is your ideal customer. Knowing who not to sell to is incredibly important as your team is building with limited time and resources. Optimize for discerning sales people who know how to acutely identify a customer’s pain, and assess how deeply your solution can solve it. Having them spin wheels on weak leads, and drain the resources of your technical and support teams, will distract and derail your progress. 

• You have a target of closing 15 new deals at the end of this quarter for our company, and a prospect list of 1000 leads. How would you prioritize/filter these leads to maximize your chances of meeting this goal? Who would you pursue first, second, etc…What additional data would you ask for to inform your next steps?

Storyteller 

Your sales hire will likely sell remotely. This means they need to have exceptionally strong written and verbal communication skills. They must also ask good questions & attentively listen. Most of all they need to sell you. Do you believe them? If you gave them a metaphorical phone book, would they know how to select, pursue, and close your most loyal customers? 

• Take some time to familiarize yourself with our product and come prepared to roleplay and pitch our team. We’re less interested in your ability to memorize all our product features, and most interested in how you persuade and engage with potential customers. 

Sales hires are not easy. And if you’re struggling with sourcing good candidates, or with a recent hire, you’re in good company. The qualities above are ideally assessed early on before you make an offer. But if you’re managing performance right now, you can perhaps gain some clarity grading your existing hire(s) against the above!

Firing “fast” or impulsively is not the take-away. The muscle I would encourage founders to build is knowing your team. Only if you really know your team can you effectively nurture or eliminate high and low performers. Here are some of my favorite ways you can develop this instinct and pattern recognition:

• Pick up the phone and call your team, often. Best if it’s not scheduled! Just pick up the phone and call your directs on your morning walk for coffee. Ask how they are doing and then….don’t talk. Wait. Honesty often follows silence, and you want honesty. You want to really hear how your leaders are doing. You’ll begin to develop a more personal relationship which will help you learn things about them and your business that aren’t shared during the formality of a team meeting or 1:1. 
  
  These regular calls will also help you develop a fuller picture of how your team handles stress over time, and what they’re motivated by to ultimately help you, help them. This is not a “gotcha” exercise. It should be obvious but is worth saying – a team member letting their guard down and sharing their stress should not trigger a performance plan. Instead, these calls have the potential to clarify your perception of people, or in some cases, correct it entirely (ie they’re not a low performer, their strengths are misaligned with your ask of them). 

• Ask your team who they’re grateful for at work lately. Or phrase to your liking (who can’t you live without?) But you get the idea. In your 1:1s ask pointed questions to better understand who in the organization is shining. Top performers will become clear after you ask this a dozen times. Some rising stars are not the best self promoters. By better understanding who enables your team to execute you can more quickly identify emerging talent. Then, nurture and scale that talent across the organization to multiply overall output. 

• Conduct an end of month people pulse with your co-founder. To add a formal solution to our toolkit, a quick 30 minute “end of month people pulse” with your co-founder and possibly a few execs, is worthwhile. This 30 minute sanity check is designed to be dispassionate and specific. Use the template below to facilitate a discussion with your co-founder around who’s shining and who’s struggling. Push yourself to be concrete  – save venting for another time. Note the specific behaviors that demonstrate how someone is shining/struggling and what next step you both can take to either double down on what’s good or course correct what could be a train wreck. This is a very easy meeting to depriotize because it’s not a metaphorical fire that needs to be put out. Proactive exercises like this are hard to protect on your calendar. But it’s worth it. This conversation can expedite your instincts…ie you do in fact have a problem that needs correction. It can also improve your leadership, reminding you to thank and check in more on your top performers. 

The added benefit of really knowing your team? Understanding what talent gaps are missing so you can acutely solve for them with future hiring. Also understanding what talent exists but that’s untapped so you can reallocate resources or promote from within instead of solving problems with hiring. My favorite, however, is adding levity to your day. These spontaneous calls don’t always yield a huge “aha” moment, but instead, a closer connection to a colleague or good laugh. Pointed questions like “who are you grateful for at work lately” is a boost of serotonin. And honoring a meeting like the end of month people pulse can leave you feeling more aligned and calibrated with your co-founder. 

Collaboration Hours

Every day from 1-4pm the entire company blocks off time for collaboration hours. During collaboration hours, there are no external meetings allowed and everyone must be available for their teammates. For co-located teams it means everyone must be in the office from 1-4pm, but can work from home beforehand and after, if desired. For distributed teams, the entire company needs to be online and available – personal appointments should be booked around this window as should external meetings with clients/vendors/investors/candidates etc. Collaboration hours bring the entire company together, daily, for 3 consecutive hours – whichever 3 hours you choose.

For co-located teams, this is a particularly valuable strategy as employees find it frustrating when they go into the office and their colleagues decide to stay home that day. Even founders are irritated when this happens – one told me “I am the CEO, and I am the only one in the office today, everyone else is working from home.” For remote teams, it’s not a perfect solution, however, it sets important boundaries and consolidates your team’s attention. You can make announcements on slack that people are likely to read in real time, problem solve quickly with a phone call, and create space for long brainstorm sessions on zoom that otherwise are impossible to book across 3+ people’s calendars, especially if it’s longer than 30 minutes. Collaboration hours manufacture some of the serendipity and efficiencies of IRL work while still reaping the benefits of remote work (potentially happier employees, broader talent pool etc). 

Executive Co-Location 

Employees can work from anywhere, but executives must work from HQ. One founder shared that they hire anywhere in the US, but executives must work from the same city. Given the importance of this groups’ chemistry, and the frequency in which they meet, I found this strategy interesting. Founders with remote exec teams invest in more travel because meeting in real life 4x a year with this group of people simply isn’t enough. And the opportunity cost of misalignment with your exec team is extremely high. Co-locating with your 3-4 top executives saves you money (less travel), time (less calendar tag), and runway (more alignment —> more output —> more investors dollars). This may mean you miss out on an A+ CMO candidate who won’t move, but it’s an intentional trade off that may be worth making if you’ve experienced frequent tension with your exec team that resolves when you meet in person.

There’s no right answer here! But hope the above solutions provide you with additional options to consider as you build and scale your teams. 

Founders are always slammed, always. I can’t recall a founder ever telling me – “my afternoon is wide open.” Every minute of every day is scheduled. And if there is a rare, unscheduled block of time, it’s quickly filled with responding to texts, slack, email, or an ad hoc call or meeting. A provocative question for founders if the above sounds like you – are you busy or productive? 

They are not the same. Busy feels productive, but it’s not. It’s actually counterproductive. Every hour of your day is insanely valuable – and it’s so easy to fill those hours by saying yes to things you should say no to. It’s important to say no – so you can ensure at the end of every day, you were productive, not busy. And by productive I mean, investing your time in things that move the needle for your business by an order of magnitude. Here’s a framework for how to think about whether you are spending your time (busy days) or investing your time (productive days) as a founder/CEO. 

1. You’re told you’re wrong. 

If there are meetings you have with certain investors, colleagues, advisors, coaches, friends, or employees that leave you thinking about problems in a new or different way, you are investing your time. These are meetings to keep on your calendar, to perhaps even increase in frequency. Try to get more time with this person, or group of people, to talk/brainstorm/vent, what have you. Reduce time/frequency of meetings that do not inspire new ways of thinking. As the CEO and founder, you are unlikely to be told no, or you’re wrong by your team very often. So it’s important to lean into those relationships that prompt you to think differently about how to approach a problem. 

↑ meetings with people that inspire you
↓ meetings with that don’t move the needle intellectually 

2. You feel energized/focused/excited. 

Be mindful of what activities bring you energy, focus, and excitement. This can feel counterintuitive – a long walk, however, is more productive, than sitting in a meeting that drains your energy. Skip meetings that deplete you. It is busyness masked as productivity. And replace that time with activities that leave you with clarity of thought. If that means your calendar every morning is protected and unbookable – so be it. 

↑ activities that provide you with clarity of thought
↓ meetings that deplete you; outsource these (or remove them entirely)  if possible

3. Your CEO/founder title matters. 

There are some things only a CEO/founder can do – one of which is fundraising. Sure you may involve your COO or other team members, but if you’re serious about fundraising, you are having the initial meetings with investors, and pounding the pavement with your narrative. You can’t outsource this task. If you don’t run point on the fundraise, who will? Hiring is another example. Courting top talent and key execs is a team effort, but it’s driven by you. If you want to snag an exec at Amazon, you have to drive it. Strategic hiring is so important, and those best hires expect to be courted by the CEO/founder. Lastly, looking around corners. Nobody else in the company is looking around corners the way a founder and CEO does. Keeping a pulse on your competition, setting and communicating  ambitious OKRs/targets for the team, or thinking about strategic areas of investment/partnership is your job. You can’t count on others at your company to drive this – even if you’ve hired the best and brightest. If you are so slammed in meetings every week that you have no energy or time left to wear your CEO/founder hat and look around corners, you’re busy, not productive. 

↑ increase your awareness of tasks only you can do, prioritize this work
↓ time spent on activities that others can and should do

Add to this a market crash, tech layoffs, slower fundraising cycles, and countless twitter threads on how to keep the lights on, the stress is real. Emergency breaks like reducing burn to extend runway, being disciplined with hiring, and giving yourself more time to fundraise than before, are table stakes.

Perhaps not so obvious is making sure you and your cofounder are ok. On top of everything mentioned above, the last thing you need is tension with your copilot.

Today we want to resurface an article we shared back in November about how to stay connected with your cofounder when things are uniquely challenging.

Zoom more, slack less

You’re putting out fires, multi-tasking in meetings, and sitting in back to back video calls all day. So when it comes to ad hoc communication with your co-founder, you likely fire off quick updates or asks via email/slack/text. Right? Why add one more “meeting” to your day? It’s easy to take for granted the trust you have with your co-founder which is why you may find yourself cutting corners with communication – discussing critical things, otherwise worthy of an in person meeting pre Covid, on a super casual platform. While not feasible or probably a good use of time to always zoom, sanity check the last 30 days of your co-founder/exec team communication. What percent of your communication was via email/text/slack vs video? If you’re seeing each other less than 50% of the time you interact, you may want to shift mediums to protect your relationship. Yes! Actually protect it, with eye contact, and tone of voice. Lots can be lost in digital translation, and your co-founder is one person you can’t afford to be out of sync with.

Your 1:1 is sacred, protect that time

No time to talk? No pressing agenda items worth reviewing? Just saw them in another meeting 10 minutes ago? Doesn’t matter! Your regularly scheduled meeting with your co-founder is sacred. Do not reschedule or cancel if you can help it. This is the most important meeting on your calendar in any given week! Your co-founder 1:1 is your time to connect, regardless of content or competing priorities, with arguably the only other person in the company (or perhaps in your life?) who intimately understands the challenges you face running a startup. Honor the time, talk about the weather, your weekend plans, what you had for lunch. But don’t cancel.

Call while walking the dog

If you break up zoom fatigue with a walk to get coffee, or a quick stroll with the dog, you’re in good company. Most of us restore our sanity and improve the malaise of zoom life with some fresh air on a daily basis. But if you were once working side by side your co-founder in South Park, you likely swung by their desk before hitting Blue Bottle or the Creamery (RIP!). You would recharge together. For many, circumstances have changed. You may work in one state, your co-founder in another. The casualness of a coffee break, together, was an important one. For many, pre-covid life allowed for more unscripted, unscheduled downtime with your co-founder. But you can still have this apart. On your strolls for coffee, or walking the dog, call your cofounder, just to say hi. Inserting that casualness into your formal remote relationship will grease any potential tension you’ll have down the road.

Get bored together

If you’re seeing your co-founder or exec team quarterly IRL, you likely have a few days together in the same city that are full with meetings (some together, some not), and as a result, your catch up may be overly transactional. There’s simply not enough time to talk about everything, so you hammer through glaring topics without leaving time for silence. Yes! Silence. Awkward, long, silences, when it feels like there’s nothing left to talk about. That silence, together, once led you to a conversation, that led you to an idea/product/business that you’re building right now! Make room for that silence again. Manufacture silence by adding more time to your rare IRL meet ups. Get bored together. Do nothing together. Quite literally exercise, eat, scroll twitter….together. Give your mind time to wander with your co-founder, and see what great ideas you think of next.

My calls with colleagues in Asia are fascinating – I am both looking into the future and into the past when I hear about their days. In some ways, COVID has left a lasting impression on businesses and consumers in China and Taiwan, with certain behaviors fundamentally changed for the foreseeable future. In other ways, it’s as if COVID never existed. If you’re curious what behaviors today the US may carry into the future once the virus is controlled, and which behaviors we may not, we can look to Taiwan and China as examples.

Below, I’ve shared our current observations of the before/after impact of COVID in these markets across 5 categories: remote work, tailwind verticals, public health policy, founder mentality, and travel. 

Remote Work 

• COVID Impact: In early 2020, tech workers in Taiwan and China worked from home exclusively. As restrictions eased, employees returned to half occupancy offices. Today, nearly all tech workers are back in the office – 5 days a week! In the US, many companies have committed to remote work through the end of 2020 and into mid 2021. Some have embraced a completely remote first culture and many, including those in our own portfolio are renegotiating and cancelling/subleasing office space entirely. 
  
• Key Takeaway: This may be an area where cultural differences heavily influence behavior as remote work before the pandemic was uncommon in Taiwan and China. So in some ways, it’s not surprising most businesses have returned to a 5 day in-office work week. While the US and Silicon Valley in particular seem more comfortable with long term remote work strategies, it’s worth noting that sustained “zoom fatigue” will influence return to office decision making. 

Tailwind Verticals 

• COVID Impact: Before COVID, meditation and mental health were considered niche markets in China. Usage of sleep and meditation apps were low; it was not considered a growth vertical. Additionally, there was no mainstream narrative around the importance of mental health. During COVID, 42.6% of people in China reported feelings of depression and anxiety and the demand for mental health support grew. Today,  momentum remains strong. Some apps in this space like Tide, are seeing 2X growth in their DAU users. 
  
• Grocery delivery is another area where pre-COVID, grocery apps were used primarily by millennials and younger consumers. Older shoppers were less likely to download and use a digital platform to buy food. During the pandemic, strict lock downs and social distancing measures shifted previously offline shoppers online. Perhaps reluctant at first, all ages and demographics began to rely on digital platforms like Missfresh to buy groceries. After months of usage, today grocery stores in Taiwan and China remain quiet as previously offline shoppers have remained online with a new appreciation for the ease and efficiency of grocery delivery. 
  
• In terms of productivity, pre Covid, WeChat was the platform for business and personal communication. Business meetings were conducted on WeChat group calls. Consumers would have dozens of active personal and professional text threads. With lockdowns, all communication was remote and the demand for video emerged – driving the popularity of “WeChat Work” and adoption of Zoom. Today consumers continue to use video in lieu of international travel and WeChat work is sticky as ever with over 200 APIs for enterprises to accommodate their workers “on the go.”
  
• Key Takeaway:  If your business has experienced a tailwind from COVID, there’s a good chance it’s here to stay. This is an opportunity to convert customers for the long haul, and diversify your users. Previously unreceptive customers may become future evangelists. Nurture this swell in interest and be open to exploring ways to penetrate a newly unlocked market further. 

Public Health Policy

• COVID Impact: In most parts of Asia, wearing a mask while sick was customary pre COVID. When COVID hit, everyone wore a mask preventatively, all the time. Today, most people in China and Taiwan wear masks only on public transit, or in hospitals/clinics. Some businesses like banks require a mask as well. Otherwise, few wear masks preventively anymore. In China and Taiwan, temperature checks are still common before entering an office, mall, or restaurant – indoor venues where it’s hard to socially distance. Large events like concerts are uncommon in China but operating as usual in Taiwan. 
  
• Key Takeaway: Public health best practices previously uncommon in the US like mask wearing are likely here to stay, particularly in healthcare settings and possibly in schools and on public transit. Handwashing and hand sanitation stations, and an increased focus on ventilation/indoor air quality are other examples of public health policy and infrastructure that will endure beyond the pandemic. 

Founder Mentality

• COVID Impact: Capital efficiency and cost savings were top of mind for founders in China and Taiwan when COVID was rampant. Many founders were optimizing for extended runway wherever possible. Today with COVID currently controlled, founders remain cautious with cash and domestically focused. Hiring is intentional, low performers are managed out quickly, recruiting candidates in hard hit verticals like travel is common, and international expansion is deprioritized with global markets harder to access.  
  
• Key Takeaway: While much of life in China and Taiwan is back to normal, entrepreneurs remain operationally and financially disciplined. There is no shortage of hunger and ambition, founders continue to pursue aggressive growth – just not at all costs. There’s remnant conservatism around fundraising and an increased focus on healthy unit economics that we suspect will be true for US founders as well. 

Travel

• COVID Impact: During COVID, cities and state lines were locked down and as a result, international and domestic travel plummeted. But with COVID at bay, domestic travel in China and Taiwan is booming – there’s palpable pent up demand. In Taiwan, domestic tourist spots are full of locals. Some airlines are launching virtual travel experiences where a consumer travels nowhere on stationary airplanes but enjoys duty free shopping, and airplane meals served by flight attendants. In China, the government is considering issuing additional duty-free licenses to certain merchants to boost domestic consumption. 
  
• Key Takeaway: With most countries imposing travel bans on American travelers, it’s fair to anticipate domestic tourism will pick up and new creative experiences will emerge to accommodate unfulfilled wanderlust. If you’re building a consumer business, there may be an opportunity to capture this demand for a creative “staycation” and engage your community and future customers in new ways. 

As always, we will continue to share our observations and learnings as the pandemic evolves abroad. In the meantime we hope there are a few insights that resonate today.