5 principles for effective remote work: how I spend my time as a solo capitalist
optimize for deep work, take fewer meetings, work your outbox, build for scale
There’s a great deal of curiosity surrounding the rise of solo capitalists and how we work behind the scenes. How do we spend our time? Who helps behind the scenes? What tools, workflows, and systems make the model possible?
Solo capitalists are responsible for sourcing, winning, and supporting a portfolio of companies. We are held to the same standards as firms with teams that own each step of this process, which means how we spend our time directly impacts our ability to win allocations in today’s hyper-competitive fundraising climate.
Building on the 3 ways to activate your army of investors, I wanted to share the guiding principles for how I work as a solo capitalist. I have a fully distributed team and work with specialized freelancers on design, community, talent operations, and editorial because our model requires sector specific experience and freelancers help us expand our network and collaborate with other companies in our category.
To increase our overall output and contribution to individual portfolio companies, I looked to my friend Mathilde Collin who openly shares her calendar and how she spends her time as the CEO of Front.
You can read more about how she spends her time here.
For some background, here’s the deck from Worklife Fund I and the strategy for Fund II. I’ve also included 10+ posts on the changing landscape of venture capital in the appendix if you’d like to go down the rabbit hole later.
How I spend my time: optimized for deep work ie: market research and big rocks with portfolio companies vs. traditional sourcing such as networking.
A typical week:
The 5 principles for effective remote work:
Optimize for deep work
Align on big rocks
Batch routine asks
Work your outbox
Build for scale
1. Optimize for deep work
Why deep work?
Less context switching, weekly goals are clearly defined, and preparation for meeting new companies is baked into the model.
Tangible outputs: Concrete projects with portfolio companies and proactive big rocks with companies that we’d like to back in the future.
Worklife investments in Hopin, Public, and Webflow were catalyzed by independent market research, proactive emails to founders, and specific tactics to earn an allocation and continue to follow-on with larger allocations in later rounds.
In today’s environment, prioritizing your time effectively and allocating a significant amount of time to proactively deliver value ahead of an investment is critical to securing an allocation.
On average, I meet founders at least 4 months before they go out to raise money. In most cases, we validate an idea together before they leave their current company. This requires whiteboarding, strategic customer introductions, and a more bespoke approach to recruiting the right people at the right time based on specific superpowers and tangible playbooks from their previous company.
For every new investment I ask three questions:
Can Worklife immediately add value? This is how we earn an allocation.
Will our community events impact the trajectory of the company? This is how we earn larger allocations over time.
Does the founding team of each new investment have operating experience that adds value to the rest of the portfolio? This is how we build for scale.
Considerations and tactics:
For founders and investors in the early stages of brand building for their company or firm, allocating an amble amount of time for deep work ensures time for publishing thought leadership and developing tangible case studies that speaks to the quality of your work. In the new era of building in public, openly sharing company strategy to support the broader ecosystem, the teams that do this well are the teams that allocate sufficient time and resources to make it a priority.
For founders and investors that have an established brand, you may find less deep work and more meetings is more effective because you’re able to close candidates and new investments based on your reputation.
To optimize for deep work, I take fewer meetings and learn from the sidelines
Take fewer meetings
As an angel or a new manager, it’s easy to fill your week with a lot of first time meetings or get caught on the hamster wheel of replying to every opportunity that comes inbound vs. thoughtful engaging with a handful of companies where you can immediately add value.
The investors that move fast and with conviction are ones that come prepared.
I find blocking time before and after a meeting is an effective way to come prepared and deliver value after the first meeting: make customer intros, source new candidates in your network, and circulate notes with next steps.
More meetings run the risk of a shallow discussion and without time blocked before and after each meeting, the follow-up emails and action items lose their effectiveness over time. Time kills deals, and I’ve seen first-hand that persistence pays off (even if it means building a relationship, proactively finding ways to add value and investing at the next round.)
Learn from the sidelines
As an angel investor, I analyzed hundreds of companies before ever writing my first check. This was partially due to my role at Zendesk working on product integrations, competition, and building Zendesk for Startups. I also found that refining my own mental models for how I wanted to work with companies made my pitch to founders more compelling over time.
If you’re new to investing, your operating experience and professional network can immediately add value however many investors continue to specialize or refine their value proposition so it’s specifically designed for the jobs to be done at the earliest stages.
While it’s tempting to start writing checks immediately, many venture firms encourage a new general partner to wait up to a year before writing their first check.
Prior to starting the firm, I invested in a few emerging managers to learn alongside other investors before making the leap to full-time investor. I found this was one of the most effective ways to scale my time as an operator by learning alongside other investors with fewer 1:1 meetings with startups.
2. Align on big rocks
An effective way to align on expectations before making an investment is to commit to “big rocks,” tangible ways that you will help the company succeed.
I hear from founders that the smallest checks are the most helpful checks, aka “workhorses” on the cap table. But as a small check, it’s up to you to determine how you’d like to work with companies.
Some examples of Big Rocks:
Customer Intro Engine: shared document that tracks customer pipeline and roadblocks with specific actions for investors, founders, AEs, business development leads. I batch these introductions as routine asks (see #3).
Customer roundtable discussions: invite-only discussions to bring together companies and target customers in a format that’s educational and not transactional. We believe industry discussions are a more effective way to build a relationship than traditional sales pitches.
Learning circles: monthly learning circles for first hires including first DevRel, growth engineer, product designer, and head of people (80% of Worklife companies are remote-first and most are remote-only which requires a unique set of internal processes: employee onboarding, company culture & benefits, employee retention).
3. Batch routine asks: The jobs to be done for early stage companies are fairly repeatable and I find they are best completed in a single block of time.
Email introductions: warm intros are easy to execute, but the volume makes introductions a significant part of an investor’s week. I have multiple blocks each day to triage all texts, emails, and intro requests at once.
I use Texts.com to streamline all messaging and find the LinkedIn integration is a great way to send more proactive messages to source and close candidates for Worklife backed companies. I use OpenPhone for all work-related calls, so my assistant can help triage and track texts, voicemails, and adhoc calls.
But we find recruiting at the earliest stages is a bespoke process which requires context on the superpowers of individuals who have done zero to scale before.
Closing calls: offering time to meet with candidates who have passed early screens. On an average week, I spend up to 15-20% of my week on these calls.
Venture is by definition a very long-term game, so these calls create an early, direct touchpoint with every person who joins a Worklife backed company. Many new hires have said they plan to start a company in the future, so I’d like to be the first call when they’re ready to do so.
This has been an especially helpful strategy for meeting female candidates, planning long-term career goals, and introducing peers and mentors from the Worklife network. I shared more on this strategy in TechCrunch.
Talent falls into three categories:
Sourcing: creating a bespoke list of candidates in your network
Closing: offering time to meet with candidates who have passed early screens
On these calls, I share why I’m excited about the company (market size, value of equity, quality of team) and walk through specific questions related to the offer letter.
Pave’s compensation data lab is a helpful resource for evaluating salary, equity, and benefits against other venture-backed startups.
Success: introducing mentors, peers, and helpful operators in the ecosystem to set every new hire up for long-term success
4. Work your outbox
While at Zendesk, I planned one day per month where I focus solely on proactively sending emails to continue to invest in relationships I’ve built over time and continuous expand to people that I’d love to meet and have learned from along the way (many of my closest friends started out as internet friends 😊):
1. Check-in with an old boss or colleague
2. Cold email someone that I’d love to meet ie: someone working in a similar role or someone I follow on Twitter who I’ve never met
3. Schedule Lunchclub meetings to expand my network and meet like-minded people
In the same way we spend 4 months or more with operators before they leave to start a company, many of the executives that have joined Worklife-backed companies have been friends of the firm who host Worklife community events, speak at SaaS School, or meet companies informally while they’re evaluating what’s next.
As an investor, my network is now a critical component of the overall success of the firm so I block time each week to proactively engage with operators in my extended network.
I continue to look for creative ways to work with new people that I meet:
5. Build for scale
While venture has historically taken a high-touch and more bespoke approach to working with companies, in many ways it was similar to an enterprise sales process with steak dinners, extravagant gifting, and strategies that require a lot of face time.
Today, we see more operators and founders raising their own funds and using the same tools and workflows that a startup would use to scale their time and automate routine tasks.
As a firm, we designed all of our touch points around repeatability, relevancy, and responsibility.
A few systems we’ve implemented:
Individuals asks are turned into group conversations
Leverage the operating experience of founders in the portfolio
ex: Equals founder Bobby Pinero was the first Finance hire at Intercom. He built and led the finance and analytics function for 7 years and scaled from $1M to $200M.
Executive round tables: bring together executives to discuss a timely topic
Our monthly roundtables cover topics related to remote work, return to office, company culture and values, and create opportunities for Worklife founders to engage with leaders from other companies like Cameo, Reddit, 100 Thieves, MSCHF, and more.
Everything we build, we share (as templates)
Annual meeting is a large-scale event for portfolio company to close new customers, vs. a closed-door conversation with our investors
You can find all of the panel discussions and workshops on our YouTube channel.
As always, I’d love to hear from you. If you’re thinking about time management and systems for working asynchronously, I’d love to learn from you 😊.
Some helpful thoughts on venture and the rise of solo capitalists