As an operator and active angel investor, I left Zendesk a year ago to build Worklife, a future of work focused fund, backed by Silicon Valley investors and executives from breakout $1B+ companies.
While there are many paths into venture, I’d like to share my background, fund strategy and how I raised $5M in just two weeks (and chose to raise $10M based on a lot of interest from other sector-aligned founders) to help other operators, angels and emerging fund managers break into what I consider to be one of the most high impact and meaningful jobs in the world.
It’s an honor and a privilege to partner with founders on the long road to success. If nothing else, I hope this post inspires you to get involved with early stage companies in some capacity. Startups require so much more than capital to be successful.
- How to start angel investing
- Why start a fund?
- The pitch
The pitch is an early version of the deck that closed Marc Andreessen, Zoom CEO Eric Yuan and Silicon Valley investors and executives at Dropbox, Slack and other 🚀companies.
How to start angel investing
Like many angel investors, I got started by meeting early stage on evenings and weekends, while I was operating full time at Expedia and later Zendesk in various product roles and lastly in a GTM strategy role where I built Zendesk for Startups which included a network of incubators, accelerators and VC firms.
In addition to operating, I taught classes at General Assembly for over four years and built my own GTM bootcamp as a way to expand my reach and build a trusted network with 5,000+ operators in the Bay Area (many have gone on to start companies).
I then decided to rebrand the program as it’s own stand-alone entity and call it SaaS School, a self-funded & community-led program taught by executives from Airtable, Dropbox, Notion, Superhuman and other venture-backed startups.
In my recent interview with TechCrunch, I shared that “you start by advising, then you start with very small angel checks.”
Today, there are a number of programs to get started ie: First Round Angel Track, AngelList Spearhead (up to $1M for founders) and most VC firms operate their own variation of scout program.
In the beginning, I used my own capital to invest in early stage companies including Webflow, Command E, AirGarage , but most importantly I sent a high volume of companies to VC funds.
Through Zendesk for Startups, SaaS School and other events I hosted, I became a super-connector in Silicon Valley.
I would take the first meeting and help founders find their lead and access other angels in my network.
A few thoughts for those who are just getting started:
- Access is everything when you’re just getting started: meet a lot of companies and start to narrow your filter over time
- Lean into existing networks: Venture capital is an industry built on trust and reputation. Your reputation with colleagues and peers at other companies matter a lot, especially as they leave to start companies or you want to recruit them to your portfolio companies
- Give, give, give before you ever ask for anything: Before raising a dollar for my fund, I had taught over 5,000 students, hosted weekly startup dinners and jumped on diligence calls when firms had questions that aligned with my experience in SaaS growth and GTM
Why start a fund?
While there’s no shortage of scout programs or ways to play an active role in the early days of a startup, I chose to start my own fund for three reasons:
- Values alignment: People spend 1/3 of their lives at work. Technology has the power to create new jobs, improve existing ones and give people more control over their career progression without employer dependencies.
- Market opportunity: “I had friends like Ryan Hoover, who started Weekend Fund focused on consumer, and Alexia is one of my friends as well and I saw what she was doing with Dream Machine, which is also consumer. It felt like it was the right time to come out with a SaaS-focused fund.”
- From SaaS School alone, I see 200 applications twice a year from Seed and Series A founders. There was increasing demand from the community for a dedicated program to technical/product founders learn GTM best practices from leading experts.
- Skills alignment: The ability to partner with founders where I can immediately add value through operating experience, network and general interests was a core driver for not joining a firm. I wanted to stay focused and continue to develop my craft as a bottom-up SaaS and workplace product expert.
The Pitch
Worklife is a future of work focused fund not tied to “Consumer” or “Enterprise” labels, but rather focused on new tools and services to unlock individual potential through creativity, productivity and new types of work.
Here is an early version of the deck that I used to pitch early LPs.
Overview:
Bullet points to describe the fund strategy and high signal LPs involved.
Fund I has a fairly high number of investments by design.
The goal is to build a broad network that aligns to my core thesis. I’m anticipating 70% of companies will fall under the “work” category and 30% will fall under “life” such as education, childcare and services that are consumer, but directly impact your work life.
About slide:
value proposition to founders, achievements and fund differentiators
Market opportunity:
Define the market opportunity and provide examples of companies that align to your thesis.
In this case, my LP base is focused on Silicon Valley investors and executives with deep expertise in the space, so this section is fairly light.
Theme slides:
A key trend, unique insight or thought that demonstrates access, expertise and ability to win deals aligned to the theme.
In this case BYOT is a term I coined to describe tools that people discover on evenings and weekends, bring to work and land & expand inside of companies.
For creative tools such as podcasting, publishing, design platforms for architects, jewelers, graphic designers and animators, these tools grow through influencer adoption and social mentions, industry communities and creative agencies/freelancer platforms.
One of the core pillars of @WorkLifeVC is new technology that reimagine work.
The greatest innovations we’ll see in the workplace will come from new consumer tech that people discover & use daily to improve their work life. Technology gives consumers more leverage to advance their career without employer dependencies.
People want more ownership over their career and flexibility to seamlessly transition into new sectors and areas of expertise
People (not employers) will solve problems like career progression.
Affordable skills-based education is giving people more ownership over career progression @LambdaSchool and @WhiteHatGB accelerate & launch high earning careers not possible before @knowablefyi@superhi_ for ongoing learning to accelerate careers or start something new.
Online communities and forums create a compressed learning environment & safety net for members – Peers share insights and validate ideas – Members collectively refresh content & moderate – Safe space to job hunt or start something new @ThePracticalDev@girlboss
Professional coaching, on-demand advice & remote workspaces create new outlets for people to break into a new field Interests snowball into careers: self-education & consistent publishing to build expertise Interest based calls like Dial-up https://dialup.com
GTM for software companies is increasingly similar to DTC brands: brand matters, community reduces customer acquisition costs and customer support costs and social signals drive purchase decisions over pure functionality.
Your work life is part of your identity.
For early builders, you’ll have periods with long hours and insane focus but at the end of the day you’re building what you love.
As you scale, keep in mind: people spend 1/3 of their lives at work, it’s a big part of who we are and how we view the world.
The modern workplace is a community with shared values, a discovery platform for new goods and services and a trusted source for news and information.
Offices are designed for Instagram.
Employees choose companies based on benefits and services.
Companies compete on culture.
I recently told Harry Stebbings on 20 Minute VC that “great company cultures aren’t coincidental. It requires insane focus and a commitment to company values.”
Fund Strategy slide:
A clear definition for how you plan to source, pick, win and support companies.
Track record:
List angel investments and advisor roles to demonstrate both access and deal judgement.
In this case, Webflow had received raised a $72M Series A from Accel and all angel investments were alongside top-tier firms or high-signal angels in the cases where I invested before a priced round.
Personal brand:
What are you known for in the ecosystem? Why would they pick you over other angels and micro-funds?
Access & Scale:
How do you currently meet founders? How will you help your growing portfolio with limited resources?
Fund strategy:
Target fund size, average check size, carry & management fees.
Strike zone:
What companies and align with your thesis and fit within your strike zone of sourcing, picking, winning and supporting.
Note: LPs also look for examples of companies outside of your strike zone, however I have removed outside strike zone slides to avoid any signaling risk for founders.
