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I’m working at Chicago Ventures as Entrepreneur in Residence, a unique position that I believe will make me a more strategic founder for years to come. Second-time founders are strategic First-time founders usually build products based on personal interests. If they’re lucky - with the right timing, market, and early adoption - they might get to work on that thing forever. Repeat founders take a more sophisticated approach, learning from their past mistakes. The first two companies I started were based on personal interests. I started Kubmo in college to teach women in developing countries how to code. Our product resembled a non-profit coding bootcamp more so than a technology startup. I learned that revenue strategy matters just as much as solving a problem. My second company was Moonlight, a platform for software developers to find remote work and get paid weekly. This startup had meaningful user value, automation, traction, and VC funding. Here, I learned the growing pains of scaling a two-sided marketplace where supply and demand have competing needs (hint: the payer wins). I also saw these patterns as an employee at Fitbit and theSkimm.  James Park, the founder of Fitbit and serial entrepreneur, was inspired by the technology of Nintendo Wii and identified personal health data as a market wedge. Fitbit started by selling one-off tracking devices to consumers, then formed partnerships with distributors, and eventually found a subscription software approach for more long-term predictable revenue. His prior experience as an entrepreneur led to a more mature business strategy than other early competitors. First-time founders Carly and Danielle started theSkimm in 2012. They were early adopters of the email newsletter movement, writing witty news for a focused audience of professional millennial women. They built a loyal following, garnered investment from VCs like Google Ventures, and attracted splashy coverage from mainstream media. The content was beloved, but they never monetized beyond manual ads and sponsorships. In contrast, second-time founder Chris Best watched this newsletter trend and launched Substack - the infrastructure for any creator to write and monetize their content with a subscription. They have over a million people paying subscriptions to writers on the platform, and they keep a 10% cut of payment volume  Repeat founders have a huge advantage, they’ve gone through the motions many times. They understand what matters when deciding on the right co-founders, early team, investors, market, distribution, revenue strategy, and so much more that can only come from experience.  From MBA intern to Entrepreneur in Residence Last summer, I was planning my move from Brooklyn to Chicago to start the full-time Booth MBA. Apprehensive at the thought of returning to student life, I went to Twitter and typed - ‘best VC firm Chicago’. The top post was from Steven at Chicago Ventures - [https __bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com_public_images_ea1cbbd3-3067-4084-abb1-8e2eec88eb25_2106x1587.png] After three rounds of projects and interviews with each member of the team, they offered me the position. I was eager to update my LinkedIn profile with a lofty new job title - MBA Intern. For the past 9 months, I’ve been working at Chicago Ventures and immersing myself in the world of early-stage venture capital. I manage sourcing sprints, network with founders, lead pitch meetings, and support partners through the diligence process. Most importantly, I join partner calls where decisions are made. These meetings are the best education I’ve gotten on what makes founders backable and what investors look for as early indicators of a successful business.  Fast forward to last month, and I was feeling burnt out. I was taking four time-intensive Booth classes, spending at least 20 hours a week at Chicago Ventures, and in the early stages of starting my next company. I was sacrificing the social aspects of the MBA experience, and cutting out sleep and exercise.  As I weighed my options, Jackie and Peter (CV partners) took me to lunch with a proposal that I stay at the firm in a new role - Entrepreneur in Residence. They knew my intention was to start another VC-backed business, and I was learning more relevant skills by working at Chicago Ventures than in most of my business classes.  I accepted the offer, excited to continue working in the immersive world of VC while starting my next company. How working in VC has made me a better entrepreneur My experience in VC has transformed who I am as an entrepreneur in three important ways. Knowledge: I understand startups as an asset class. A fund is made up of a management team that raises money from limited partners (institutional investors, corporate funds, family funds, etc) who are seeking high-risk, high-reward investments. Venture capital is one of the highest returning asset classes, and LPs are expecting a high return. Investors are looking for entrepreneurs who they believe will create a big enough outcome to return the fund, if not 10x the fund. Venture capitalists are not simply investing out of intellectual curiosity to build something cool that justifies a Series A round of funding. Their job is to take other people’s money and turn it into more money. If all the portfolio startups fail, they won’t be able to raise another fund. This context helps me to focus on what matters, set the right goals, and imagine a compelling outcome where incentives are aligned. Network: I have successful advisors on my side. There are approximately 1,965 VC firms in the US, employing a median of 6 employees. It’s a relatively small industry that’s relationship-based with an ‘up or out’ mentality. New people enter the business either via personal connections or through a mentorship program like an internship or residency. The intention behind mentorship programs is to bring more diversity to VC firm leadership, startup executive teams, company boards, and angel investing. Working in VC has unlocked access to a tightly connected network of investors, founders, and operators. It’s already opened up doors that were not available to me in the past. Today, I get casual mentorship from partners and successful entrepreneurs. In the future I’ll be able to leverage those connections when I’m raising money, recruiting, or pursuing an exit. Confidence: I know the process and the investor’s point of view. I used to be intimidated by investors - they appeared to have all the power. It seemed unfair and random to watch homogeneous founders close big funding rounds without much traction. There are certainly power dynamics at play, but I’ve gained a lot of empathy for how hard it is to identify good businesses and for the responsibility of investing other people’s money. Investors, like serial founders, are confident because they’re experienced and have done the same thing many times over. They see hundreds of companies and have a clear thesis on what leads to meaningful outcomes. I’ve gained clarity on what it takes to communicate a long-term vision that inspires trust. — I believe that entrepreneurs with experience in VC have a similar advantage to second-time founders. They have additional layers of context to understand how things work and why they matter. I hope more funds will invest in EIR roles and similar programming to further support the startup ecosystem. Interested in becoming an EIR or hiring one? Read more about the structure of the EIR position on the Chicago Ventures blog here. [https __bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com_public_images_c2479e95-24fe-44e6-8899-a00a8f0dbeed_1600x600.png]

I’m sure you’ve all heard the news that the future is here. It’s distributed, it’s crypto, it’s NFTs, it’s web3, and it’s all leveraging blockchain technology. The world’s most ambitious technologists are building infrastructure to transform art, music, money, identity, regulation, government, passwords, and documents. Really any exchange of information.  I’m here for this future. I believe the next phase of adoption is about education, accessibility, and regulation.  My journey with crypto My first experience buying Bitcoin (according to Coinbase) was in 2017. It felt similar to the volatile and opaque world of stock investing. As an early Fitbit employee, I had experienced the stock price post-IPO go from $16 to $60 to $7 before I could sell any of it - meaningfully changing my compensation package in ETRADE. With Coinbase on the other hand, I could see my investments moving daily and I could cash out at any time without blackout periods. I like taking bets, and experimenting with this new world was fun and exciting. I read a few books like Bank 4.0 last summer, thinking I would build a neo-bank designed for women. While I worked through a variety of potential ideas, my prototypes always centered around the idea of a personal identity controlled by the individual. It felt like a future blocked by national borders, bureaucracy, and an archaic financial system. This past December, I was walking on the 606 in Chicago when I overheard two women in their 60’s explaining Bitcoin to each other. I opened my Coinbase wallet to a surprise $500 in BTC I had forgotten about. As a student, this was a welcome present from the past. After a few inspiring conversations with web3 friends (thanks Jae, Lauren, Syd), I decided to spend my spoils investing in a DAO and buying an NFT on OpenSea. Why a DAO and an NFT you might ask? Because they were the only places I could readily spend crypto without cashing out to fiat. The easy part - I found an NFT and a DAO I liked. The hard part - spending many hours watching bro-tastic TikTok videos on how to transfer funds the right way and optimize gas fees. The process for this particular DAO was to buy an Avalanche token, make a MetaMask account, add the extension to chrome, add the Avalanche network, transfer it back to Coinbase, pay the gas fees to transfer back to Metamask ($5 - 10), then create an account with the DAO, figure out staking and “buy time” for the DAO, then buy in.  Once I emerged from the rabbit hole, I decided to just keep my money in Coinbase. Thinking back on each product I’ve worked on over the past decade - the biggest problem is almost always around the onboarding funnel and retention. Once you acquire new users, how do you keep them retained? The potential for innovation and a democratized economic order is exciting in web3. But it seemed that the basic best practices around user experience and adoption have been forgotten. Smooth like Velvet Since August 2021, I’ve been spending my free time validating ideas. I created three marketing websites around patterns that consistently came up in conversations with friends at that time. (1) Buying engagement rings, (2) Rental payments, and (3) Crypto payments. Each of these segments started with a consumer problem that could be solved with software, and also had an underlying business model in technology infrastructure and B2B2C. Please note these are rough value-prop websites to test a market. These are not product launches or even close to what we’ll end up building. Think of them similarly to Amazon’s famous exercise of writing a press release before starting a new initiative. Learning quickly and adapting We scheduled user interviews around each idea. The qualitative data showed clear trends almost immediately. We started canceling meetings because the feedback was so consistent after about 15 calls.  Here’s a quick overview of learnings: [5fbafeb4-772d-495f-a091-2cae2b30f88a_1800x810.jpg] Velvet Rings Discover your unique wedding ring, split the costs + get insurance, enhance or trade any time. People liked talking about this idea, especially those with private equity or affluent backgrounds. De Beers and Tiffany & Co put out ad campaigns starting in the late 1940s that created a mainstream perception that diamonds are the meaning of love (“A diamond is forever”). Our initial hypothesis was that people wanted a more modern approach to marriage including equity splits, insurance, and even easy storage of marriage certificates and prenups. We were generally proven wrong - people like the traditions around marriage. We found that women wanted their partners to spend a lot of money on a big diamond, and their partners were willing to do it. Wealthy people have family jewelers and pay in cash, and price-sensitive people are looking for a deal. This idea evolved into more of a pure e-commerce play (like Warby Parker), and less of a long-term relationship with the consumer (like Lemonade on the blockchain). We quickly decided this wasn’t the right business for us. [https __bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com_public_images_fd099f4c-4af6-4f12-a43a-5364fcb2abaf_1800x810.jpeg] Velvet Rent Velvet helps you decide on a home you love, gives you rewards and credit for paying your biggest expense (rent), and builds your trusted financial identity for life. People understood the need for this consumer rental payments layer, but it began to feel like a vitamin instead of a painkiller. They agreed that rent payments were outdated and difficult, but they were generally okay with it (“a necessary evil”). They write checks, send broken-up payments through Venmo, or begrudgingly use building management software designed for the 90s (hey, Elevated Living). Paying rent becomes part of their monthly financial routine, even if it’s relatively manual.  When we talked to people in competitive markets like New York City and San Francisco, it was more of a pain killer. We still think this product should exist (payment splits, flexible deadlines, rewards, credit building, service bundling), but likely as one part of a larger platform or in targeted geographies where it’s most needed. [https __bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com_public_images_c4ff509c-d321-4920-ad3d-aff7020ac7c8_1800x810.jpeg] Velvet Cash  Pay people, stores, and for anything online using our app & card. Spend and manage your money using any currency - from Dollar to BTC to Yen to ETH. This proposal felt polarizing and controversial to a mainstream audience (note, posted in early 2022). The first website was written to target a less sophisticated audience than the average crypto product. Everyone had an opinion about why this wouldn’t work or why they loved it. The most common objections were ‘the US government will never let this happen”, “it’s too volatile, I don’t trust it”, or simply “I don’t understand”. People wanted to talk about it for most of the call and were curious even in their hesitancy. Most people thought of crypto as an investment, rather than as a tool or a new technology. The lack of accessible applications makes it hard for the average consumer to start experimenting in the ecosystem. This is the space where we’ll be focusing our attention moving forward. It will evolve into something very different moving forward. — Update: Check out the Velvet website for where we’re at today.

People with MBAs have a bad reputation in the world of tech startups. Elon Musk devalues the skillset (“they don’t know how things work”).  Peter Thiel famously pays young people to drop out of school to start companies and doesn’t like to hire MBAs (“extremely herd-like thinking and behavior”). The world’s most successful tech founders never even finished their college degrees. Just to list a few: Mark Zuckerberg: Facebook, James Park: Fitbit, John and Patrick Collison: Stripe, Jack Dorsey: Square and Twitter, Steve Jobs: Apple. An MBA is not a requirement for any career, and it’s even frowned upon if you’re aspiring to be a tech entrepreneur. I knew this, and I still applied to business school with the sole focus of being a startup founder after graduation. What patterns do you see in that list of entrepreneurs who dropped out of school to find huge success in tech? They’re all men, and most still had the pedigree of being accepted to a school like Harvard or Stanford. When I started researching women who made it to a similar level of success, the pattern was slightly different. Most finished college (yes, there’s still a strong Harvard contingent), and many have Master’s degrees or MBAs. Sheryl Sandberg: Facebook and LeanIn, Jennifer Hyman: Rent the Runway, Katrina Lake: Stitch Fix, Anne Wojcicki: 23andMe, Michelle Zatlyn: Cloudflare. It’s also just harder to find examples of successful woman entrepreneurs since only 2% of Venture Capital funding goes towards female founders.  — After my co-founder and I sold Moonlight in 2020, I decided business school was next.  I spent the next year working as a technical product manager, taking online business classes, learning GRE/GMAT math, and hustling to get enough scholarships to offset the risk of my entrepreneurial plans. Chicago Booth offered me a spot in their full-time class of ‘23 along with the Herman Family Fellowship for Women Entrepreneurs. I gratefully accepted. Their flexible curriculum is more amenable to entrepreneurs than other schools, and includes the opportunity to compete in the New Venture Challenge with investment of up to $1M for winning startups. Companies like Simple Mills, GrubHub, and Braintree had come out of the program. One quarter in, I’ve learned invaluable lessons I wouldn’t have prioritized on my own time. I used learnings from entrepreneurial discovery, microeconomics (this required teaching myself calculus 😭), and statistics classes to validate or disprove each of my startup ideas. I learned the math of insurance prices, how it serves as income distribution in some ways. I understand more about credit card fees, the cost of calculated consumer risk. I got access to Nobel Prize-winning economists, world-renowned entrepreneurs, and meaningful experience as a VC investor while interning at Chicago Ventures.  More than anything, I’m gaining access to a prestigious world I’ve never had access to in the past. I’m spending my time with world-class investors, executives, academics, lawyers, consultants, bankers, and aspiring politicians. I can feel the doors of access and privilege opening up around me. It would have been easier to stay in my comfortable bubble. I could have kept my job, skipped the rigorous MBA vetting process, then coded and launched a lean business in my free time. But I believe the humility of resetting as a student, the time away to truly learn, and the access unlocked by a top business school will lead to a more impactful long-term outcome for me as a founder. I intend to increase the 2% of Venture Capital funding that goes towards female founders as an entrepreneur myself, and eventually as an investor. I expect to report back that this MBA was one of the things that increased my chances. 

The term you’ve probably heard before is a search fund  - where an entrepreneur raises money to acquire and run a company. The goal is to find an existing opportunity with potential for an exit, kind of like house flipping in the real estate market. I consider myself a search founder, constantly seeking my next venture-scale business idea to build from the ground up. I’ve worked in startups for the last decade, experiencing the roller coaster ride of entrepreneurship as both an employee and a founder - and I’ve been lucky to experience everything from stagnant growth to fundraising to acquisitions to an IPO. During the pandemic, I had a lot of isolated time for reflection. I realized my primary skill set and passion is around being an entrepreneur. Whether as the founder of a company or working as an employee, I find myself rethinking the status quo, iteratively building things, and creating organizational change with others. Now I’m pursuing an MBA at the University of Chicago Booth, with the primary focus of discovering my next startup idea to work on after graduating. Most of my peers in business school are taking part in a more known recruitment cycle like banking or consulting. I’m choosing a far riskier path, without any guarantees. So, I want to hold myself accountable and share my journey with you here. How I got started in Silicon Valley  I started my career in San Francisco as an app product designer in 2013 - it was my dream job at that time and I felt so lucky to be there. After working at a product consultancy called AKQA for a year after college, I realized I liked going deeper on one problem rather than giving other companies short-term advice. I used a new job marketplace called Hired to find my first startup job, at an early-stage fitness app company called Fitstar.  I loved my new startup life at Fitstar. We shipped an iOS app to millions of subscribers, then launched the platform on web, Android, and Apple Watch. I was learning from smart people, working on a product I loved, and even got to design a personal passion project of mine - Fitstar Yoga.  Six months after joining, Fitstar got acquired by Fitbit, and suddenly I was a product designer at one of the best-known consumer brands in the world. The product design team alone at Fitbit was made up of 60+ designers, split into specialists in ‘human factors engineering’ and ‘user interaction design’. Again, I was given a growth opportunity to learn from some of the best designers and engineers in Silicon Valley.  Fitbit went public in 2015, just a few months after I joined. We celebrated the ringing of the NYSE bell at 6 AM in the brand new San Francisco office with champagne and Fitbit-designed mini cakes. I had experienced the full upward trajectory of the quintessential startup story in less than a year - from joining a scrappy team of 10, to being acquired and given meaningful ownership, to seeing the Fitbit founders do a roadshow and go public. I was in awe of the non-traditional career path I had been fortunate enough to find myself in. I worked hard for the next two years, becoming more specialized in mobile app development, and building a network of as many smart entrepreneurs and product people in San Francisco as I could.  Becoming a founder I left Fitbit in 2017, looking to move away from San Fransisco and live as a digital nomad. I had a few consulting projects lined up with early-stage female founders I met in SF - like Simple Habit and Modern Fertility. I got a virtual mailbox to maintain residency in California (don’t ask me why I chose that state 🤷), sold all my things, and found an international insurance plan. The first city I moved to was Mexico City, where I spent four months with my partner. Friends from San Francisco and around the U.S. were curious, wondering how we managed to live this international lifestyle but maintain a Silicon Valley salary (this was before remote work became ubiquitous during the pandemic). We started to realize there could be a business model around this working style - living remotely, working in SF. To test it out, we bought a domain (moonlightwork.com), put up a Squarespace site with a Typeform, and posted it to HackerNews and Twitter. Within a few days, we had thousands of signups from developers looking for highly paid software work. Over the next two years, we hustled to bootstrap the remote work marketplace while living in 8 cities around the world. Once we figured out a sustainable subscription model, we raised money from institutional venture capitalists and hired a remote team. We moved to New York City, with a roadmap to double down on growth and automation. (If you’re interested to read more about the Bootstrap journey, read my interview with IndieHackers here) When it came time to raise a second round of funding, it was early 2020. Coronavirus was on the horizon, VCs were cooling off on investments, companies stopped hiring, and Moonlight had not achieved the hockey-stick subscription growth we promised to investors. The team was burnt out from three years of building, evangelizing, acquiring, and scaling the business - and our investors offered to introduce us to three potential acquirers. After a few weeks of negotiations and conversations, we got an acquisition offer from one of the startups. We took the offer and the deal closed - Google-backed PullRequest bought Moonlight and gave us offers to join the team and keep growing the platform. All considered, we were ecstatic to end the Moonlight journey with an acquisition. I joined PullRequest for three months through the transition, then left to join theSkimm as Lead Product Manager up until I started business school. On the search for something new Being an entrepreneur is addicting. It’s the opportunity to discover a secret insight and imagine a future that’s different from today, then work relentlessly to make it happen. I think there are lots of ways to take on an entrepreneurial role, even as an employee working within a larger organization. During my time at theSkimm, I was able to identify an opportunity with a forgotten mobile app, create a new strategy and roadmap, then hire a team to re-launch the subscription platform. This opportunity to create change kept me as activated in many ways as being a founder, but with the stability of a great paycheck and supportive benefits. But in the end, I was working towards someone else’s dream, which has its limitations. A year and a half after selling Moonlight, I finally have the headspace to start thinking about something new. What’s the next opportunity I want to devote myself to? The must-haves in my next startup: • A product that needs to exist in the world and that solves a large problem • An end-user who I care deeply about • A clear path to monetization that doesn’t require ads • Venture-scale growth The big unknowns I’m looking to discover this year: • What problem I’ll be solving • The exact industry (broadly within fintech) • Who my co-founder(s) will be • Yes, I realize these are really important unknowns! So, I’ll be writing about my discoveries here. I won’t have all the answers and I’ll surely be wrong in my assumptions. If you read something I get right or wrong, if you want to get involved, if you have ideas, please tell me about it.  Your feedback is always welcome, and thank you (really, thank you!) for following my journey.  Oh, and wish me luck! I’ve got about 18 months to figure this all out before I finish business school in May 2023:)