AMA session with Brianne Kimmel, Founder and Managing Partner at Work Life Ventures, a future of work focused fund investing in tools and services for people at work.
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Brianne is an investor in Webflow, Voiceflow, Tandem, Command E and 20+ other startups. Brianne previously worked on the go-to-market team at Zendesk focused on self-serve growth, technology integrations and built Zendesk for Startups. She stumbled into SaaS while she was Head of Social Media at Expedia leading paid acquisition, customer support and community. Today, she runs an invite-only program called SaaS School for startup founders to learn from the fastest growing companies like Airtable, Drift, Dropbox, Slack and more. Work Life Ventures is backed by Marc Andreessen, Chris Dixon, Matt Mazzeo, Alexis Ohanian, Garry Tan and other investors in Silicon Valley.
Hi Brianne! As a newer fund, how do you source deal flow? How do you establish an ‘edge’? Do you have a scout team?
Feel like no matter how high quality the team or how good the market, early pitches can often just get lost in the noise, or sometimes new startups complete their financing very quickly with preexisting relationships or by running a tight, competitive process with established VCs.
I recently published The Angel J-Curve which covers how to get started as an angel and best practices for new funds, I typically find differentiation comes from your both fund size (stage/sector/check size) and how you source, pick, win & help companies.
For me personally, I keep a fairly flexible calendar so I can jump on deals that gain momentum and make sure I don’t miss out on great companies. I’m fairly “outbox focused” which means I keep a list of companies that I want to invest in and spend more of my time helping them.
Hi Brianne, thanks for taking the time! For post revenue investments can you share if there is a sense of average ARR to funding ratio you’ve seen across deals? And/or if you’ve seen a separation of this ratio across cohort and stage?
I love Point Nine Capital’s Funding Napkin, it’s a good framework for benchmarking post-revenue companies.
That said, SaaS companies in today’s market are getting preempted more than previous cycle, so I encourage founders to spend time with VCs and thoroughly vet who will make a good board member. Get to know your investor well before they write the check.
Hi Brianne! Thank you for doing this AMA! How would you recommend pre-seed B2B SaaS founders think about building out their advisory board?
It’s great to hear you’re already thinking about advisors at the pre-seed stage! SaaS is increasingly ubiquitous, so I would take an intellectually honest look at where you’d like to go and who can help you get there. Many execs use angel investing and advising as a way to track companies that they may potentially join at a later stage. Find individuals with relevant experience and strong cultural alignment. Is there network immediately valuable today? Would you want to hire individuals from their previous companies?
Hey Brianne, thank you for making time. Would love to have you share your thoughts on the current angel investing landscape?
Also, just read this piece by Alex Danco about how angel investing in the bay area is often done more for social status rather actual investment returns. What is your take here? Is this a perverse incentive, or a net positive for founders?
Completely agree with Alex if you’re what I call a “show horse,” individuals who serve as a strong social signal for follow-on investors.
For early career operators, many build a track record applying their operating experience on evenings and weekends
Hey Brianne, thanks for taking the time to do this AMA! Love the thesis behind Work Life. Lots of talk now and over the past few years about no-code, remote, and other changes to the way people work. What thing (or things) do you think will change the future of work, but people aren’t really aware of or talking about yet?
Community is a real driver for professional development. Seeing a trend where developer connect with hiring managers on Dev.to when they aren’t looking for a new role.
Designers are open sourcing their designs on Figma Community & Webflow.
The people you meet in Slack channels like this can open more doors than any employer
Know you’re pretty active on Twitter. Would you say there is a big disconnect between the hive mind of “VC Twitter” (ie. the hype, jokes, and sensationalism) versus reality when it comes to the startup investment landscape and experiences of real boots on the ground founders raising money?
Some argue that venture was previously a sales role, now it’s a marketing role. Meaning founders/investors were previously tied to a pitch & investors “closed” the deal via a real sales motion: working sessions, dinners, etc.
With more VCs creating content and the proliferation of new funds, I think venture is shifting back to a sales role.
The best VCs have a brand/public persona but more importantly can quickly win/close a deal, so founders can get back to work.
Does being a fully remote and distributed team affect or reduce acquisition or exit opportunities? How does a large 500+ person company that is primarily in-person integrate a fully remote startup? With the rise of remote work, this is a question I have not seen answered anywhere by investors.
Really great question, I think this will all come down to the culture of the fully remote team. Does it feel like a group of freelancers and contractors or have they build a well-oiled machine where the sum is greater than its parts.
Continued discsussion of this question on Twitter
Hi Brianne! Work Life seems very focused on the experience of individual employees… What do you see as the biggest challenges (and product opportunities) around building an engaged, happy, and mentally healthy team?
This is really top of mind, with the shift towards remote I think knowledge spill-over will become a challenge for remote teams. People learn from each other by simply sitting next to each other. More here.
Some of the companies you’re involved with seem very product-driven and focused on the needs of users rather than stakeholders. How does this change the sales and marketing approach for those companies?
It’s a very different strategy from traditional enterprise where customer development is more collaborative rather (building alongside top operators) than authoritative (big companies require specific features).
What resources do you recommend for learning how to improve your negotiation skills?
I read a lot of books and listen to a lot of podcasts on this. Never Split the Difference is a great starting point!
Been hearing a lot about the big 3 levers that investors can provide to founders: 1. check (eg. size/terms), 2. network (eg. connections, introductions, prestige/signaling), and 3. platform (eg. tech, resources and support). Do you agree? Which is most valuable? Platform seems like a new concept.
I would also add “brand” to network. Does the firm serve as a strong signal to future investors and hires.
All are valuable, but you’ll find founders will optimize for each differently. If you’re a first time founder, many optimize for brand & platform for more operational support as they scale.
What are your thoughts on the ‘creator economy’ and the rise of monetization platforms like Patreon and Substack? Does this new paradigm of ‘work’ fall under your investment umbrella?
As machines get better, humans get more creative. Seeing a shift from AI/ML focused companies to new ways for people to make money for their creative skills.
Interested in how you approach portfolio construction. What is right check size? In your mind, what delineates seed investment from pre-seed?
Right now, I’m seeing repeat founders raise a small friends & family round ($500K) before a fairly large $5-8M seed from multi-stage firms.
First time rounds are more likely to raise a traditional seed with room for angels/scouts.
Have to ask this, what books have most greatly shaped your view on the world?
Bowling Alone, and Enlightenment Now. I love Steven Pinker’s books.