Office Hours: I'm the president and COO of Feather and was a founding member of Birch Run Capital.Featured

Hello! I am Ilyse Kaplan, President and COO of Feather. At Feather, we're reinventing furniture rental for the next generation. I joined to head up finance, and have had the privilege of growing with the company ever since! Currently, I lead all aspects of the organization including growth, technology, and operations. I also sit on the Board of Directors and play a critical role in charting the future of the company with our investors.

Earlier in my career, I was a founding member of Birch Run Capital where as an investor and operator, I helped scale Regis Corporation, Sleep Number and other portfolio companies across manufacturing, real-estate and retail. I also spent a few years post-graduation living in France helping launch men’s skincare brand Anthony in the European market.

I am deeply passionate about elevating women in the workplace and beyond. I support Girls Who Code and Laboratoria where I hope to help level the playing field for women early in their careers. Since COVID, I've been living as a digital nomad across Panama City, Oaxaca, Michigan, Colorado, California, and New York. After 1.5 years of being on the road, my husband and I just settled for the year in Ann Arbor, MI!

Ask me anything about growing a company, leadership, venture capital and everything in between!

Thanks so much for joining us @ilysekaplan!Elphas – please ask @ilysekaplan your questions before Friday, September 10th. @ilysekaplan may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
So exciting! I'm co-founder of Lodgeur, which turns bare apartments into on-demand housing. Very familiar with Feather and delighted to see you here. Our CEO is Anglo-French, focused his graduate research on the ROI of quality design, and loves the design aesthetic of Feather. I'd love to know how you found high-quality talent to help scale, when your company was in that awkward phase of growing too big for the current team and yet not quite able to pay for great talent. I'd also love to get a quote from you for a piece I'm writing on digital nomads, if that's something you'd be interested in. The premise of the piece is that the pandemic merely accelerated an existing trend (more people becoming digital nomads) and that the demand for housing that doesn't fit neat 12-month sprints is going to continue to rise. I think people tend to believe nomadic life is an all-or-nothing choice, although it may be more of an episodic experience for some people.
Hey Brooke, thank you so much for the question! I actually lived in France myself following university, so I feel an instant connection to your design-loving CEO :) Feather also recently expanded our operations into five markets in Texas this past June— including Houston! If you’re interested, I’d love to connect outside of this forum to see how we could work together. The short answer to finding the right talent is that Feather targeted folks (like myself) who had a high enough risk tolerance to join an early stage startup where they believed in the mission and the business model, and who were willing to forgo cash in favor of equity. We still needed to pay reasonable salaries so that folks could pay the bills, but the equity packages that we offered earlier-stage employees were designed to compensate them for the relative risk inherent in taking a lower salary at a company that might not be around in a year. We found people in a variety of ways, leaning more heavily on our personal and professional networks rather than recruiters. I was actually introduced to Feather by a friend of a friend who was previously Feather’s main relationship manager at Silicon Valley Bank (which has been our primary bank since the company was founded). Another colleague met our CEO at a mutual friend’s party, and ended up interviewing. Our current head of remarketing— who works to find a home for furniture no longer redeployable within our system— joined us as a Taskrabbit delivering furniture and grew his career with us from there! Everyone who joined Feather in the early days wore a lot of hats. Ultimately, if you have a business with exciting upside, you will find the right people to come on board— but you need to look hard, and at times in unconventional places. In terms of being a digital nomad this past year— I’d be happy to speak about this at length! I have always been an avid traveler. Before COVID, I used to visit 3 new countries every year and have been fortunate to visit about 65 countries in total. Feather’s shift to being a remote-first company in April 2020 gave me the opportunity to continue to pursue my professional aspirations while also pursuing my personal interests. I first joined my now-husband in Panama City, Panama in March of 2020 before starting the digital nomad lifestyle, renting a bunch of Airbnbs and short term rental units for 3-10 weeks at a time. Having just landed in Ann Arbor, Michigan for the year, I am now enjoying the calm of being in one place— though I can definitely see myself becoming more nomadic again in the future!
Thanks so much, Ilyse. I'd love to connect offline at [email protected]. We are also looking to expand in the other Texas cities by year end, so we'd love to learn more about your capabilities there. Feather was more expensive than Nickson when our CEO last spoke with Jay, but the Feather design standard is the best we've found.We posted a job listing about 8 hours ago and have over 100 applicants already, so I'd also love to learn more about how you identify the hidden gems from a large pool. Aptitude vs. experience is the current debate we're having.
Hi Ilyse, thanks so much for your time this week! Huge fan of Feather's concept so congrats on all your successes!I'd love to hear more about your experience setting Birch Run Capital - how did you even get started ? Did you set up the fund first or started pooling commitment from LPs? And speaking of LPs how did you meet them? And what was your formula to make them invest (particularly interested if this was your first time raising a fund)Super excited to learn from you:)
Hey Iynna! Thank you so much for the question, and glad to hear you’re a fan of Feather! Regarding getting started with Birch Run— honestly, I got lucky. My former business partner was looking for interesting opportunities to invest some of his own capital- but since he didn’t have much money, and couldn’t risk losing the small amount he had- he felt strongly that anything he’d put his own capital into needed to be bulletproof. As a result, he was extremely thorough in documenting his analyses- I remember one that we worked on together that ended up being over 150 pages long! A few months into investing his own money, he ended up connecting with a retired businessman that was looking for exactly that kind of detailed analysis- and about a year after they connected, the businessman seeded our fund with its initial capital. It was at that time (after our first investor was committed) that I came on board. The other LPs we brought on learned about us through word of mouth. We never advertised wildly or actively sought out new LPs. I realize that my experience is not super practical in terms of advice on how to find LPs if you are an upstart investor. If I were starting again today, I’d make sure that the thesis for my fund was really well defined before I started. Who are we, and what do we intend to invest in? Why are we unique, and why are we uniquely positioned to succeed as investors in this specific vertical and strategy? I’d also give a lot of thought to who the right capital partners are. Should we be focusing on individuals, family offices, or institutional capital? Do we have a minimum check size, or a maximum? Are we most likely to succeed by raising small investments from a diverse group of seed investors— who may require lots of one-to-one outreach and management— or should we focus on mutual funds who will have more onerous compliance requirements but write bigger checks? What is the expected timeline to deploy capital, and what returns do we expect? In much the same way that I go to VCs today to pitch Feather, I’d pursue a similar process in pitching my investment fund. Best of luck!
WOWOWOW dropping so much gem on this Friday ! THIS IS GOLD and frankly the advice no one really gives you! Thank you SO much for taking the time to respond to me!
Hi Ilyse! @ilysekaplan I'm a software engineer/mid-career changer and I'm about to start digital nomading as well. But I would be interested in learning more about venture capital. Particularly does one really have to have 200k (isn't that the legal minimum??) to start or are there avenues for investing smaller amounts that I can slowly scale from?I'm not from money, nor am I a guy who was hired at a big tech firm that went public; so I only have what I have saved as a newer software engineer. But I'd love to know if getting into venture capital/angel investing is possible on a smaller scale.
Hey Cat, great question! First off, congrats on making a mid-career change— I know that it can be tough, but ultimately really rewarding if it helps you better align with something that you are passionate about. I’m also excited to hear you plan to nomad around! Is there anywhere in particular calling to you as your first stop?Your question around investing is a timely one. Historically, to participate in venture capital or similar types of investing, an individual needed to have an annual income of at least $200K (among other requirements) to be considered an “Accredited Investor'' by the Securities Exchange Commission. These restrictions were loosened last year and now any individual can become an Accredited Investor by simply passing a test. This New York Times article from last month ( provides several interesting anecdotes about "ordinary" people becoming angel investors. There are a number of investment platforms to ease this effort, and I would expect as the world of investment continues to become more accessible to consumers through platforms like Robinhood, this trend will accelerate. I know some people who have joined groups such as Golden Seeds and 37 Angels which specifically cater to women as investors and leaders of the portfolio companies— which might be a good place for you to start finding like-minded folks!
@ilysekaplan I found Elpha while researching Feather. It is great to catch up with your busy ever-evolving career status.Congratulations on your success and welcome back to Michigan.
@nancyhodari WHAT A TREAT TO HEAR FROM YOU! I appreciate the kind words on my career success - and would love to properly catch up sometime if you ever find yourself in Ann Arbor. And in the meantime... welcome to Elpha!
Can you share your career path to COO and the biggest difference/challenges you overcame or usually see from the roles held before?How would you summarize what it takes to be a successful COO?
Hi Rebecca! I see that you head up ops today at Foxbox Digital- presumably a COO role is something you might be interested in longer term?Before I became COO at Feather, I worked in the finance world— which gave me a very specific and important lens into understanding business. In finance, you’re not just working on the budget side of things— you’re working cross-functionally with all departments- often spearheading analyses that help ensure that the decisions we make check the right boxes financially as well as operationally! My time with my portfolio companies at Birch Run Capital also gave me a ton of exposure to the operations side of running a business, and once I left investing, that exposure helped guide me to my next step at Feather. I knew I wanted to be a part of an early-stage, mission-driven organization, and the stars aligned when I stumbled upon Feather. When it comes to being a successful COO, there are a few things I believe are most important. First, it’s all about the little details that make up the big picture. It’s critical that you strike a balance between understanding all the moving pieces of the business and how they work together, and also seeing the big picture. Part of the challenge of being a COO is not getting too in the weeds, while also having an understanding of what's going on at different levels of the business. In general, having the traits of a good leader are important— but specifically traits like humility, great communication skills (simplifying complex concepts to all members of your team is key) and authenticity. I think it’s important to show up as your full, true self in all aspects of your life— including work! Lastly, it’s impossible to do anything successfully without the right partners. I know I wouldn’t be half the COO I am today without the fantastic team at Feather— who are all experts in their respective disciplines. I know I can count on them, and they in turn know they can count on me to lead Feather to success.
Thanks so much for joing u us for office hours Ilyse! Would love to learn more about running Birch Run Capital as well - what were some of the biggest challenges of scaling your portfolio companies across real estate and retail?Also, after living in all of those places, why did you pick Ann Arbor, MI to settle into for the year?Thank You!Briana :)
Hey Briana! There were many ups and downs at Birch Run Capital, as there are at any investment firm. While we invested in both private and public companies, when it came to the public markets, one thing that stood out to me was the lack of women in leadership roles. Sleep Number was an exception- with Shelly Ibach (still serving) as CEO, and a host of other impressive women on the leadership team. It was rare for us to even find companies with more than one female board member. I’m sure you also understand how isolating it can feel to be the only voice representing women in the room— so I’m happy to see that the tide seems to be turning with more diverse voices making their way into senior leadership roles. In the real estate space specifically, there was the challenge of the post-2008 mortgage crisis. It was a double-edged sword for us— providing both new opportunities, as well as significant challenges. Regardless of the industry, one of the biggest roadblocks I encountered was finding the right partners. When you’re investing, you’re not just investing in the company— you’re also investing in the team, which means finding the right people is paramount to success. We could fall in love with the mission behind an organization, but if the team wasn’t a good fit— it was a pass. Regarding Ann Arbor— We’re really loving it so far, but I have to say that my decision to live here was totally unexpected! My husband and I spent about half of last year in Mexico and Panama, before we made the decision to move. Part of the reason we chose this beautiful city is because of its diversity, especially since my husband is Colombian. Ann Arbor is a university town, which means there are people from all over the world flocking here to pursue advanced degrees. We were also drawn to Michigan more broadly due to how (relatively) insulated it is from climate change thanks to the Great Lakes. That last bit ties in to my general passion about sustainability and environmental stewardship, which is another big reason why I do what I do at Feather. Our mission is to keep furniture in homes and out of landfills — considering nearly 20B pounds of it hits the dumps each year, making up 7% of all the trash we create. We accomplish this mission through our circular business model, as well as by designing durable, high quality furniture that lasts a long time and is easy to refurbish rather than toss.
Hi Ilyse! I'm a project manager in biotech who is also working on building a genomic startup. We will begin pitching to VCs soon. Do you have advice on what VCs look for when listening to startup pitches? Thanks!
Hi Sheela! For very early stage businesses, VC’s want to see opportunity. You may not have it all figured out right off the bat, but if you can show you have: 1) A clear path paved to achieving something novel (ideally with a moat to protect you down the line) 2) A solid plan surrounding the business model and economics (to demonstrate that you’ll be a responsible fiduciary of capital) 3) The right team (capable to work together to bring your ideas to life) … you’re setting yourself up for success. During your pitch meeting, I recommend finding unique ways to get the partners to engage with you and ask questions. But from what you shared, it sounds like you have the right background to demonstrate credibility and potential for success! Wishing you the best of luck on your journey.
Thank you!