A Week in the Life: Haley Daiber (Unusual Ventures)
Haley Daiber
Senior Associate
What I Do
Most of my time is spent on sourcing- at Unusual we are pretty theme/thesis-driven, so “sourcing” typically means outreach to companies within spaces we are interested in and connecting to operators with particular domain expertise in those themes. Outside of sourcing, I spend time on diligence for current deals we are evaluating, and supporting portfolio companies that I’m involved with. But honestly, every day is different!
Week of 10/14 - 10/18
Monday 10/14
Mondays are pretty typical of a lot of venture firms- Monday morning team meetings! I try to reserve Mondays for internal meetings, diligence, and outreach instead of meeting new companies.
6:00 am - Get moving! I live in San Francisco and commute to our main office in Menlo Park on Mondays, so the day starts early to optimize for the 101! The typical routine is coffee/shower/say “good morning!” to our two kittens before getting on the road- the goal is to be in the car by 6:45 am (7 am at the latest!).
6:45 am - 7:45 am - Today Show Radio Channel 108 Making the commute enjoyable is key to starting the day off right. Sometimes I try to be productive and listen to tech podcasts (20min VC, TC Equity, Software Engineering Daily) or audiobooks, but then I started realizing that I was missing out on current events and life outside of Silicon Valley, so now I find myself making the most of my SiriusXM subscription and tuning in to Today Show Radio. It’s the best! Hoda, Savannah, Al, Craig - the whole gang I just love. The show has such a positive attitude, and they spotlight wonderful people from all across the country on the behind the scenes Sirius clips.
9:00 am - Unusual Team Meeting
This is our standing meeting with almost the whole firm- right now we all still fit in one conference room but it’s getting tight! We spend the time going over current deals at the term sheet stage or in diligence, things to note on our portfolio companies, and internal firm items like marketing, content, and events/programs.
11:00 am- Sync with Jordan on Data Labeling
One theme area that we’ve been looking into as a team has been around tools for machine learning, and one space in particular that kept coming up was the bottleneck that labeling the data has created in the process. There are “big” (big from our perspective since we focus on seed) companies like Scale AI that are helping address some of these issues, but it’s still really manual, so there’s a wave of newer startups that are approaching the problem in a different way. Jordan Segall, another associate on the enterprise team at Unusual, and I have been spending time talking to lots of startups in the space, so we are syncing up to review what we’ve learned and put it into more of a thesis.
12:00 pm - Team Lunch in the Courtyard
Enjoy the fact that we live in California and get some sun :)
1:00 pm - Enterprise Investment Team Meeting
This is the meeting where we (myself and Jordan) discuss current deals that we are evaluating, and bring up to John, our managing partner, the deals that we think warrant some additional meetings or diligence. We get feedback and then come up with action items. There is one company that we are currently evaluating that I need to do some additional diligence on this week before meeting them again on Friday.
2:00 pm - Call with Abhi
Call with our new technology resident, Abhi Sharma, to discuss his thoughts on one of the companies we are evaluating. He has experience working with someone on the founding team, so we really value his input on the team in addition to the technical merits of the company.
3:00- 4:30 pm - Sync with Rae on upcoming events
Our Director of Content and Community, Rae Dinh, is organizing a couple of upcoming events that I am providing some input in terms of the content. We are starting a speaker series for our founders in which we are bringing in experienced operators on a topic. The first one is with Sahir Azam, SVP Cloud Products & GTM at MongoDB focused on Open Source 3.0. John has a lot of experience supporting companies surrounding open source projects like Cloudbees (surrounding Jenkins) and Heptio (surrounding Kubernetes), so this is a topic we’ve been spending a lot of time thinking about, especially at the Open Core Summit that we recently attended.
4:30 - 7:00 pm- Outreach/organize/emails
This is a job where there are always lots of balls in the air, so I spend the rest of the afternoon trying to make sure my agenda for the rest of the week and priorities are clear, and that I’ve responded to time-sensitive emails and taken the action items needed on diligence. The remainder of the time is focused on additional outreach to people/companies.
7:00 pm- On the road again
On Mondays, my brain is usually a little fried, so I try to mellow out by just listening to music on the way home. My favorite stations are PopRocks, 90’s and 2000’s, and AltNation, but I love almost all genres. I’m from Austin so have to be a music lover!
Tuesday 10/15
6:30 am- Wake Up, Peloton, get out the door
On Tuesdays I typically work from our San Francisco office, so I have a bit more time in the mornings and try my hardest to get a work out in. I’m a product junkie and early adopter of a lot of things, so I gave in quickly to the Peloton train (especially through their Affirm financing option and Unusual’s fitness expense policy!).
8:30 am- Call with a data labeling company
For first calls, I typically keep to 30 min- this allows for me to give an overview of Unusual, learn the basics of the company and the origin story, and where the company is today (currently raising? Plan to in the future? Too far along for our firm?) and get some key questions answered.
11:00 am - Pitch meeting
An in-person pitch meeting for a company that I met a few weeks ago through a demo day. It’s early and not in a theme space for us, but the founder was really impressive that I wanted to meet them in person.
1:00- 3:30 pm- Angel Academy Prep
We are doing our first Angel Academy on Friday where we are bringing in operators that are interested in learning more about investing and doing a half-day workshop. I’m leading a section on how you evaluate the deal dynamics (ownership percentage, SAFE vs priced round, exit potential), so I need to go through that section again. Additionally, we are doing fake pitches at the end, so I have to prepare the slide deck for my pitch. This is the most fun I’ve had all day because my pitch is for an idea that I’ve actually thought about and talk about all the time that I’m really passionate about- breakfast tacos!
3:30 pm- Call with the Shujinko founders
Shujinko is one of the companies that I work closely with, so we have a quick call to make sure that we are all aligned (the founders, the investment team, and the “GAP” team- Unusual’s platform team that focuses on providing hiring, marketing, and sales help) on goals for the quarter in prep for our Unusual Quarterly meeting in a couple weeks.
5:30pm- Call with another one of our portfolio co CEO’s
One of the companies that I’m close with is currently fundraising, so I have a call with the CEO to discuss the process.
Wednesday 10/16
6:00-9:00 am Same as Monday Morning Routine
Except this time I’m headed to the Google Complex in Mountain View for a meeting with an operator.
9:00 am Meeting with Dave Rensin, Senior Director of Engineering at Google
I reached out to Dave after I saw his awesome keynote presentation that the ChaosConf a few weeks ago. Chaos engineering and incident response are other key theme areas I’ve been spending time learning about, and I reached out to Dave to see if he’d be willing to answer some questions I have and he generously agreed to a meeting. We had a really great discussion and I learned a ton!
12:00 pm- Pitch meeting
This company was introduced to us through another investor earlier this week and is (common in today’s environment) moving fast. Luckily it’s in a space we’ve been spending some time in, so we have some good questions/context going into the meeting.
1:00 pm onwards
We really liked the company we met at noon, so now we have to move quickly to get some diligence done (talking to customers, potential customers, backchannel references, etc.) and questions answered, as well as share with John that we want to move to a meeting with him when he gets back from Venture Atlanta later this week. I (with the help of the lovely Jenn Snodgrass!) reschedule the remainder of my meetings for the day to make sure I can focus on this.
Thursday 8/22
6:00- 9:00 am Same Routine
Except for this time I’m headed to the Goodwin Procter office in Redwood City for our Academy!
9:00 - 1:00 pm Unusual Academy
One of the programs that makes Unusual “unusual” is our Academy program. We bring subject matter experts in to teach sessions surrounding finding product-market fit and just company building more broadly. Today’s session is for both our enterprise-focused cohort and our consumer cohort, and it’s one of my favorite sessions! Adam Grant, the incredible Wharton professor and author of Give and Take, Option B, Originals, etc. will be leading the first part of the session discussing hiring practices, interview tactics, and company culture. The second part of the session is led by Unusual’s Director of Talent, Jon Volk around more tactical tips around hiring such as key questions to ask to close candidates and ATS systems.
2:00 pm Pitch meeting
Head to Menlo Park for another pitch meeting that came through Jordan’s network. It’s a good meeting, but I find myself leaning out as I’m not super excited about the market, and Jordan finds himself leaning in as he’s really excited about the team. So it should make for an eventful Monday investment team discussion! But really, I enjoy situations where we have different opinions on a company because it does allow us to really evaluate from multiple angles.
3:00 pm Update Call with AptEdge founder and CEO
AptEdge has made a lot of progress on their demo, so we go through the latest and I give feedback, and we discuss goals for the quarter as well.
4:00 pm Meeting with Abhi
Abhi is our newest team member, so we set some time aside to get to know each other better and discuss themes we are interested in. So excited to have him on the team!
5:30 pm Meeting with Amira, founder and CEO of Struct Club
Amira is based in LA but in town for a few days, so we spend time catching up and she fills me in on how Techstars demo day went. Her pitch was awesome (go to minute 59:40 to see for yourself)!
Friday 8/23
6:00- 8:30 am Same!
Typically I try to be in San Francisco on Fridays, but today we needed to have a joint pitch meeting with John in Menlo and we also have our first Angel Academy in Redwood City.
8:30 am Intro call with the founder of a popular open-source project
Really interesting meeting and project, so I get a link to the closed alpha of their new hosted product to try it out.
9:15 am Follow Up meeting with the company we met on Wednesday
We spend another 1.5 hours with the company we met on Wednesday to give John a chance to meet them, hear the story, and ask questions that he has. He was also really impressed with the company, so we continue to dig in and line up a plan to get more diligence done the rest of the day so that we can keep up with the fast timeline.
12:30- 6:00 pm Unusual’s Inaugural Angel Academy
The day mostly consists of John and Andy talking through how they evaluate companies and an amazing keynote speaker, Katie Stanton of #Angels sharing her experience as an angel and how she got started. We also have a section on legal and term sheet elements and the fake pitches! The operators have $200K to give to 4 different startup pitches. My breakfast taco startup found a few fans so I was pumped!
6:00 pm Angel Academy Happy Hour
We all head on over to Alhambra Irish House in Redwood City to get to know each other better and get their feedback on the event. Such a fun day!
That’s a wrap! This week was packed with a lot of events, portfolio co meetings, and pitch meetings, but it really does vary a LOT week by week. Definitely different from my former very planned life as a CPA at Ernst & Young, and the variability makes sticking to a schedule challenging on the one hand, but fun and rewarding on the other.
