Here’s PT 1, To VC or Not to VC

In this part 2 I’ll be answering the question: why did we have to wind down and why was it so abrupt?

Shopgirl is dedicated to sharing the profiles of luxury’s top personal shoppers & stylists. To be featured, please contact me at annwehren@gmail.com

In the fall of 2024, I was focused on restructuring our team after a leadership shakeup that summer. VCs will tell you that the team that gets you from day 1 to Seed may not be the team that gets you to the next stage (Series A). This may be true, AND leadership changes were incredibly disruptive to the business and required a lot of my attention. Managing the team and customers during the transition, recruiting, hiring, onboarding, ramping up new leaders. And the background to these disruptions is that we didn’t have a ton of money (= time) on our side. I had never raised a big round that gave me a huge buffer ($2.5M total). There was no extra quarter or two of cash to ride out a rough patch.

The reasons for this are for another post, but TLDR: as a first time, woman, non-technical founder coming from a fashion industry background with no MBA or Ivy pedigree, it’s an uphill battle to get what money you can.

I’m spending most of my time managing the team and clients and making sure we keep growing, a bit of my time fundraising extension money, and finding out from investors what they’d need to see from us to invest at the next round, Series A. I’m learning that since I’d raised my seed, the market has decided that Series A readiness is now 2-3X more revenue than the previous benchmark ($1M Revenue ARR previously now VCs want to see $2-3M ARR in marketplaces). The benchmarks are always changing. At this time, the cost of capital was going up and that means the benchmarks get higher, harder to reach.

More context: I’m pregnant and no one knows. This didn’t affect my decision making, just context on my mental state and internal clock counting down to a time in 2Q25 where I will be unavailable to lead all-out as I am used to.

Another factor is the upcoming presidential election which always slows down spend as wealthy customers (our market) on both sides of the aisle shore up spending until they see the outcome.

Q3 comes in as our lowest growth quarter ever. We were basically flat to the previous year.

With no growth, any potential investors who had inbounded to me suddenly won’t close. I halt all fundraising conversations to focus on the business.

With no new money coming in, we have cash on hand through February. It’s mid-November.

I had been in very close contact with our customers (personal shoppers + stylists) always, but especially during the leadership changes. I had hosted 60+ one-on-one meetings with them in the last 6 months. So I had an idea of what was happening and what was wrong.

It wasn’t just the election. Or the team changes. Those weren’t helping, but there was something limiting our growth that had nothing to do with anything we could affect.

We weren’t winning enough of our customers’ business.

We were building their one-stop shop. The hypothesis was, as we bring on more of the brands their clients like, we will unlock more and more of their business. Eventually capturing all of it when we have all of the brands.

We were adding the brands they were asking for. The “right” supply. But that wasn’t translating to growth in the same proportion.

Why?

I found through my interviews that we had been cordoned off to a limited number of their use cases.

Our vendors had 2 business days to ship but didn’t always hit that window. With 200+ vendors fulfilling anywhere from same day to 3+ days, delivery was unpredictable. Our customers plan around appointment timelines. They loved us, our mission, our commission, our consignment terms. But when they needed product by a specific date, they couldn’t count on us. More often than not, the stars weren’t aligned and they’d go to a retailer with next day delivery or drive to a department store and forgo commission to get their client the product right away.

We were betting on In-Seam being the right fit for the vast majority of their use cases. But the data showed the unpredictable delivery times limited our opportunity to service their clients in most cases. Of all the shopping their clients do (called their wallet capture) we needed over 50% of that amount to build the very big business we planned on and we were topping out at 10-20% wallet capture even for our most enthusiastic, repeat loyalists.

So what now? I called every investor on our cap table. I listened to our options. I thought through various next steps.

I had no warm exit paths. I’d never had the bandwidth to cultivate them. I didn’t see courting department stores worth my time when we were growing 250% YoY.

It was Q4 and any retailer I approached now would push off a first meeting to January. We were cash out in Feb. Even a fire sale may not be possible, the timing was too tight.

I saw a potential different path that solved the same problem for customers and brands. A major pivot. Away from marketplace to technology for brands to facilitate sales directly through our customers. But I’d need time to research. In order to do that, I had to stop the cash bleeding.

We had to shut down the marketplace. The team and tech burned too much cash to even keep it on in a bare bones capacity (which I modeled out also). There was no path to breakeven with even a minimal team. And I didn’t want to run a cockroach business. It was grow or die. I had to kill the current business to see if we could build a new one.

This part really sucked.

First I had to tell our investors and get them on board. I received support from most. Disappointment, obviously. No one is excited but they saw what I was seeing and trusted me. This was the saddest selling tour I’ve ever owned. Sell your own investors on why I needed to shut down the marketplace we started and convinced them to back. Ugh.

Then I told the team which was by miles the worst day of my life. The few new people were out of jobs immediately. I kept a small team on board for the rest of the year to help shut down the marketplace operations. They were amazing, gracious, and generous. I couldn’t have asked for a more supportive response from the team.

Then we had to tell our vendors and customers.

These are the days and actions of a leader where you just want to curl up in a ball in bed and not face the responses. But you do it. You manage the reactions. You put on a brave face and cry after the zoom calls.

“This is not what any of us want.”

“This is not what we set out to do.”

“I’m so, so sorry.”

But also, this is business. We tried something new. We created an entirely new distribution channel for brands. We offered our customers a totally new way to source and a new level of respect and dignity for their work I don’t think they had encountered before. I’m so proud of that.

And that’s what makes this even worse. It’s not like we were out to just make some money for ourselves and investors. We wanted to build something that changed things for our customers. That completely changed how the industry viewed, respected, and resourced them. And we did. Until we couldn’t anymore and that feeling is absolutely terrible.

In the last and final section I’ll share how I approached what came next and what I learned.

Subscribe + stay tuned for Pt 3: Pivots, acquihires, M&A, dissolution, and a (human) newborn. The end of the road for In-Seam.

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth.

Her approach to work reminds me of my own in my early career. Her resume reads as someone who is sampling the entire platter of styling options to gain experience and discover what she wants to do more of, then intentionally steers her career into “more of what I like, less of what I don’t.”

Unafraid of the grueling labor of in-person client work (retail + private client styling) and styling and assisting on photo shoots (editorial, commercial, e-comm). This is the real SCHLEP work that can be both exhilarating and exhausting. It’s the work styling in-person, physical garments on real human bodies, that separates the digital link clickers from those who produce real world results through true understanding of their craft born out of real world experience that cannot be skirted ;)

Molly’s approach to styling is not about pushing trends or certain aesthetics, rather, she gains client’s trust by helping them dress to feel more like themselves and pursue their goals which may include increasing their confidence or visibility.

How do you professionally identify?

These days I say I am a stylist on steroids because I am truly doing it all between my in-person business, assisting other stylists/personal shoppers, and working on both e-commerce & editorial shoots.

How do you work & what services do you offer?

I work both virtually and in-person: offering services such as styling, shopping, closet audits, bridal, custom, mens for my personal clients.

How long have you been doing this work?

I have been doing this my whole life but I officially became a stylist 8 years ago.

How did you start?

I started in retail! My first job was right our of college at Carbon38 when it was located in Bridgehampton. From there I learned the ins and outs of retail, worked full time all of covid at Intermix, moved to studio services in personal shopping at Bergdorf’s, landed a job with Donna Karan, then freelanced before establishing a business of my own after quitting my full time job.

Are you currently taking new clients or booked & busy?

I am booked and busy but I do have a waitlist that opens up about a month out.

Do you work mostly in-person or primarily remote/digital? If IRL, what geographic area do you service?

It’s a 50/50 split depending on the week and the client. I mostly have clients between NYC & the Hamptons but I have worked with clients all over the world and have a few clients not located in NY.

What’s your business model?

I charge hourly and offer packages. Some clients prefer an all inclusive package with an expectation of a set number of hours and I am always okay with customization.

How do you think about revenue overall? What other revenue streams do you rely on?

This is an area I am learning about more and more as I grow my business but I heavily focused on; because, at the end of the day I want to be able to pay my bills, live my life and stay afloat. I rely on my assistant work, assisting stylists and or content creators personally and or on shoots, affiliate links/partnerships, and other odd jobs.

When it comes to sourcing for your client - what factors drive your decision on where to go?

I source all over but I mostly go to my contacts first and foremost. I am so lucky to have amazing partnerships where the buys are vetted and I can trust who I am working with. I want to find what no one else is wearing so that means outsourcing outside of the typical realm of brands, looking outside of the US, on instagram, through people in the industry, I also love vintage and consignment, but I only use vetted people.

How important are commissions to you?

Commissions are important to me but they are not end all be all. Of course, I want to be compensated more for my work, but I restrict my clients’ options as a result. My job is to service my client - regardless of commission. My job is to find the perfect pieces for them and if I don’t make commission - so be it.

What do you wish people understood about styling work?

People often assume styling is mostly about aesthetics or trends, but a huge part of the work is emotional intelligence and trust. Clients are usually coming to you during moments where they want to feel more confident, more seen, or more like themselves — the clothing is just the tool to help get them there. No matter how much I vet a piece or love an outfit, at the end of the day it is the client that should make the ultimate decision of how the piece or outfit makes them feel. That is the one thing a stylist will never be able to do for someone else. We can only help execute a vision, it is up to the client to dig deep and say no matter how vetted the piece is does it make me feel excited to put on each day?

How has ShopMy changed how you approach your work and/or revenue?

ShopMy has been a game changer! It has allowed me to grow so much as a stylist and further my career not solely from a revenue standpoint but a networking partnership standpoint. I am working with brands I dreamed of working with, whether that is a discount code for my clients and or gifting for me to put my stamp of approval behind, ShopMy is not just making me think from a styling standpoint but also as an influencer and a consumer.

What’s a typical profile of your clients?

I feel really lucky because all my clients are different but the common thread is they want a little mix of everything. Contemporary to designer clothing mixed in with lots of investment pieces from major fashion houses, sourcers to find sold out pieces, vintage and consignment.

What brand or item are your clients loving right now?

ALC, Gianvitto Rossi, Jimmy Fairly eyewear, Past Midnight eyewear, Alex Crane, Mr P., Amo Denim, Dries, Toteme, Paris Georgia

What brands are you loving right now that you’re hoping your clients will get into as well?

Clyque, Elce Swim, Alemais, Kiki de Montparnasse, De La Vali

What could brands and retailers be doing better to attract you + your client’s business?

Utilizing new faces when it comes to PR/Marketing and the creative side of how a brand is presenting itself. I love being able to see real people I take an interest in to vet clothing whether its a creative director, stylist, etc. I care more about a brand being “sold” to me from a realistic POV. What I hear a lot of is that brands/retailers are marketing the wrong items. I hear complaints about quality or how something looks because an influencer was paid to promote it. I want something more realistic and organic.

What tools can you not live without to run your business?

Nove, ShopMy, Figma, and ChatGPT. I never thought I would lean into AI the way I have as a way to make tedious tasks easier to manage but I truly would be lost without my styling platform Nove. It is a one stop shop for everything for my clients.

Where can people find you?

Instagram: @mollylippert

TikTok: @styledbymollylippert

Substack: outfit visions

Website: styledbymollylippert.com

Thank you for reading Shopgirl! This work is an ongoing conversation and iteration of my mission to seamlessly connect personal stylists and their clients with the very best brands.

I’m currently helping brands connect to high-value private client stylists with a new programmatic offering. To learn more, message me at ann@in-seam.com.

This post is public so feel free to share it.

Share

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

GTM & growth strategy and execution

With 25 years in the fashion industry, Samantha has cracked away at building a business of her own for 15 years and scales her income through a myriad of revenue streams.

I love how Samantha does not shy away from speaking the truth about what brands and retailers could be doing better to attract high-value client’s business and her POV is that brand + retailer failures are what drives demand for her services. I could kvetch with her about this all day if I could ever get her to sit still. This woman is in demand.

Not only has Samantha created a winning system for her own life’s work, now she is generously sharing her successful strategies with others through a course with a description that reads like a sure-bet to make your styling work WAY more lucrative and miles less frustrating. What a boss.

How do you professionally identify?

Celebrity Stylist and Best Selling Author

How do you work / what services do you offer?

I work with private clients, on shoots, runway shows, commercial and advertorial projects. I’m launching a 4 month business course for stylists called The Standard to teach working stylists how to significantly increase their income and systemize their business for stability and long term scaling. We begin June 8th!

How long have you been doing this work?

15 years as an owner of my styling agency, Samantha Brown Style. 25 years in the fashion industry!

How did you start?

How much time do we have? I have been working in the industry since I was 14, starting as an intern during NYFW.

Are you currently taking new clients or booked & busy?

My agency is accepting new clients, yes. I personally am booked solid. I’m focussing all my extra energy (is there any?!) on launching The Standard, which begins on June 8th.

Do you work mostly in-person or primarily remote/digital?

I am back and forth between NY and Miami, but I work all over the country. Most of my services are in-person but I do work with clients virtually when I’m unable to get to them in person.

What’s your business model?

Retainer and packages.

How do you think about revenue overall?

The best way to stabilize a business is to have diverse streams of revenue. A stylist should never be dependent on one client or one stream of income. Retainers, packages, affiliate linking, commissions, brand deals and collaborations, social media contracts, consulting, public speaking...the list goes on and on!

When it comes to sourcing for your client - what factors drive your decision on where to shop from?

A stylist has to understand a client’s needs, lifestyle, body type and preferences in order to make an accurate judgement on the right designers/retailers to shop. After that, considering the client experience and where they will receive the most perks and a luxurious experience is a driving factor.

How important are commissions to you?

A nice bonus, but they wouldn’t influence my decision on where to shop–client comes first.

How has ShopMy changed how you approach your work or revenue?

I use ShopMy when I’m sending links if I’m not working through the Hue&Stripe platform. I do whatever is most convenient in the moment.

What’s a typical profile of your clients?

The common thread is that they’re busy and looking good is a priority. Overall I’d consider them high net worth individuals. They don’t want to stress about what to wear and when, and prefer the convenience of having that pressure removed from their lifestyle.

What’s your craziest client moment?

There are too many to count but one involves flying couture to Budapest to shoot overnight in a closed down museum and the other involves a client sending a private plane to take me to her wedding. Those were fun jobs! Another placed me with an A-list actor, playing heart and soul on the piano with him at Carnegie Hall. All pinch me moments…

Any wild or botched sourcing stories?

Oh yes. I was dressing someone for the Latin Grammy’s in Vegas, and even though I triple confirmed, the showroom never put her dress in the mail. It was sitting in a box in NY on a desk the day of the Grammy’s. That SUCKED.

What do you wish you knew when you were just starting out that you know now?

The expression that it takes ten years to overnight success is an absolute truth. I wish I could go back and tell myself in years 1-5 to just take a fucking breath. That probably would have helped. Ha!

What brand or item are your clients loving right now?

I’ve been really into TWP lately. They have an outlet at Woodbury Common and it’s a must-visit every time I’m up there for work. Dangerous addiction! The coolest pants and the Tiny Dancer is a dream jean, trust me!

Shopbop just released an in-house line called Le Bop. The price point is great, with your typical Shopbop aesthetic for summer staples. I’m loving it.

And, Jacquemus and Toteme are two brands I’m loving lately.

What could brands and retailers be doing better to attract you + your client’s business?

Service is a mess everywhere. I feel bad for my clients because the store shopping experience is a constant nightmare for them. They consider us (stylists) buffers so they don’t need to deal with it! Better, more efficient service in the stores would be a good start. Perks–make stylists lives easier–assist us when pulling and curating a room, run for sizes to help, ring them up quickly and efficiently, ship things on time…this isn’t brain surgery!

Is there anything else you want people to know about you or your work?

I have grown my revenue by 20%+ consistently year after year for 15 years. I know exactly the tools and techniques for stylists to make multiple 6 and 7 figures. I cannot wait to teach them how inside The Standard.

What are you manifesting this year?

The success of my course. I am so excited to see stylists’ lives change. Those who enroll will make so much more money. They will learn the skills to have a balanced schedule and a business that feels stable. No more hustling. Just growth.

What do you wish people knew about you or your work?

I think people think/assume that I’m really lucky. That’s not to say it isn’t true, but my business wasn’t handed to me through connections or access. I built every piece of this business from the ground up and made a million sacrifices to have it. The “luck” has always come from positioning–I have been strategic since day one about how to position myself for opportunities. I also have made plenty of mistakes along the way, so there is no part of this that has been easy. If it looks easy from the outside, that was also strategic :)

Where can people find you?

@Samanthabrownstyle on IG, samanthabrownstyle.com

Thank you for reading Shopgirl! This work is an ongoing conversation and iteration of my mission to seamlessly connect personal stylists and their clients with the very best brands.

I’m currently helping brands connect to high-value private client stylists with a new programmatic offering. To learn more, message me at ann@in-seam.com.

This post is public so feel free to share it.

Share

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

GTM & growth strategy and execution

At In-Seam, Charlotte was our biggest Southeast market and we drew a strong following of private client stylists, each with substantial businesses. My take on the Charlotte market is that luxury fashion demand exceeds the supply there and private client stylists are in demand to feed the needs and significant appetite by bringing in product from across the country.

Kristin Heinrich is one of Charlotte’s in-demand curators. Her approach demonstrates a commitment to supporting local boutiques first (Capitol, Poole Shop, Sloan and Vermillion a few hours away in Raleigh) while sourcing from across the country’s top stores and e-comms to ensure her clients are fully outfitted and have unique pieces their friends won’t have. Showing up to an event in the same dress is not uncommon without the guidance of a stylist in this market.

How do you professionally identify?

Personal shopper, wardrobe stylist to private clients and image consultant

How do you work / what services do you offer?

Closet Edit, personal shopping for seasonal updates, special event styling, vacation outfit sourcing and packing

How long have you been doing this work?

I started my business in 2008.

How did you start?

Funny- it started in NASCAR! I live in Charlotte and had the fun opportunity to serve as personal assistant to NASCAR legend, Jeff Gordon. Part of my job entailed dressing him for day-to-day life as well as media tours, red carpet events and TV appearances. That ignited my passion for styling and to start my own business.

Are you currently taking new clients or booked & busy? Do you have a waitlist?

I never say no to new clients. If there’s a will, there’s a way. I will always find a way to work someone in.

Do you work mostly in-person or primarily remote/digital? If IRL, what geographic area do you service?

I would say most of my clients are based in and around Charlotte, NC where I live. However, I have clients from coast to coast and I travel to do closet edits, shopping trips to NYC and other cities regularly. I also do a loads of online shopping and directly through brand partnerships which allows me to shop for anyone, anywhere.

What’s your business model?

I charge by the hour plus a professional fee on the sale. I currently do not do packages or retainers because I want clients to be able to call on me for small or large projects whenever they need.

How do you think about revenue overall? What other revenue streams do you rely on?

Partnerships with brands and stores who value the business I bring has definitely been a smart revenue strategy. It’s nice when brands and stores are in it with me- to bring the best level of service to my clients through making the process easy and rewarding for all.

When it comes to sourcing for your client - what factors drive your decision on where to go?

I source from all over - directly through brands, online and curated boutiques across the country. I tend to rely most and shop frequently with the ones who make the process fun and seamless. At the end of the day, I like to work with providers who love the process as much as I do and get just as excited about finding the perfect things for my clients. There’s a real joy in the teamwork!

How important are commissions to you?

At the end of the day, as a stylist, my clients hire me to shop for them. They trust me and take my advice on what to purchase. Where I shop and what I buy is ultimately up to me. Therefore, I choose where to spend my client’s dollars. The stores and brands that I spend with the most recognize and appreciate the business I bring.

As a small business owner, I have figured out ways to generate more revenue over the years on my sales without gauging my clients. I provide a service and want my pricing to be fair. Commissions from brand partners are appreciated but never the driving force when I’m sourcing something for a client.

How has ShopMy changed how you approach your work and/or revenue?

I currently don’t use ShopMy, but I plan to start! It’s a great way to generate revenue from a larger demographic and reach a broader audience. As I work to grow my brand, this is definitely at the top of my list.

What’s a typical profile of your clients?

I don’t have a “typical” client profile. My clients include: busy stay-at-home moms, hedge fund men and women in CA, race car drivers, banking execs, lawyers, mortgage CEOs, Uber and other billion dollar company top execs, real estate brokers and developers, college bound kids and new college grads.

What’s your craziest / proudest client moment / win? (photo?)

One of the things I’m proud of is that, even now, 20 years since I left the sport of NASCAR, I still get the call to style the winner of the Daytona 500 for their NYC media tour. I’m proud of the fact that I made a name for myself and that teams and drivers continue to reach out to me.

What was your most dramatic client success?

Having a high profile couple call VERY last minute to have me style them for TV appearances in NYC was exciting. However, I was in NC and had to navigate how to pull all of their looks from several sources from afar. From facetimes and calls to couriers and sales people literally running blocks with garment bags to meet the deadlines, I got it done! The clients never saw the chaos behind the perfectly curated looks I delivered.

What brand or item are your clients loving right now?

Lee Matthews

CELINE

Another Tomorrow

Chloé

Patou

Attersee

What brand are you loving right now that you’re hoping your clients will get into as well?

Depending on a client’s age, budget, lifestyle, I’m shopping hundreds of different brands per day for clothing.

When it comes to jewelry, I always introduce to my clients to, The Jen Collection

I have been their Brand Ambassador for 10 years. It’s a curated line of fine jewelry based in Houston, Texas specializing in hand beaded precious and semi-precious one-of-a-kind pieces, as well as an amazing collection of 14k-18k diamond and gold jewelry. During closet edits I try to encourage clients to eliminate loads of costume jewelry that’s just taking up space and upgrade and invest in a signature stack of layered necklaces, bracelets and rings.

What could brands and retailers be doing better to attract you + your client’s business?

I’ve appreciated brands and stores who have created shared photo albums for me to have at my fingertips. This is how I work with my clients and this makes it so easy for me to have access to all types of clothing, shoes, bags, accessories. It keeps me up to date on what’s new as its coming in so I can easily share to my client albums. Anyone who has worked with me knows, you won’t have to wait long for me to get options to you! I’m on it!

What are you manifesting this year?

This is a BIG year for me. My wonderful and amazing twins, Alex and Seinna, are graduating from High School in June. Both are heading off to college in the fall. As they have grown, I have had the privilege of being present while also maintaining the business that I love. Now, with more time on my hands, I can’t wait to take my business to the next level and be able to take on more projects. Traveling more will not only be inspiring but also be a catalyst to gain more clients from coast to coast while also being able to do more shopping trips with clients in other cities.

What tools can you not live without to run your business?

My phone is #1 as I do most of my work and sourcing on the go. Quickbooks for all of my invoicing and the money side of things. My brand and store partners and online sources. The relationships I build with every single client is what keeps me going. That is truly the BEST part!

Is there anything else you want people to know about you or your work?

It’s true what they say: find what you love and you will never feel like you are “working” a day in your life. I can honestly say that I still wake up excited to do what I do and feel so lucky people continue to trust me to help them put their best foot forward through what they are wearing! Also, I’m very efficient. I pride myself on jumping on something as soon as it hits my plate. When a client makes a request, for let’s say a wardrobe to take on a summer trip to Greece, it’s likely they will have a look book within 24 hours.

Where can people find you?

IG @Kristin_Heinrich_Style

www.kristinheinrich.com

kristin@kristinheinrich.com

This post is public so feel free to share it.

Share

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

GTM & growth strategy and execution

If you do, check back for Pt 2 where I get into the why and how of our wind down.

Here’s how I’m breaking out the posts:

PT 1: What it’s really like to work under VC pressure and why I chose it.
Aka to VC or to not VC.

• Bonus appendix section includes my shortlist of fundraising resources I send to every founder who asks me for advice

PT 2: Failing fast + shutting down our marketplace - goodbye to in-seam as we know it

PT 3: Pivots, M&A, acquihires, and dissolution - the end of the road for In-Seam

Now onto Pt 1.

Here’s the TLDR on what it’s really like to build a startup with VC, for the uninitiated.

For better or worse, at least the expectations are somewhat clear (also, constantly evolving and vary firm to firm) for what you should achieve and when. The benchmarks you have to hit. Very simply the expectation is Triple, Triple, Double, Double, Double. Your topline Year over Year.

When you take your first check, you work for someone else. It may not feel that way at first. They may leave you alone, the calls and requests asking how things are going, if you’re hitting your numbers and doing exactly what you told them you’d do when you sold them on your big idea, may be few and painless. But under the surface, you know. You now have a boss.

And I felt this deeply. It’s called fiduciary responsibility and I did not take it lightly. If I take someone else’s dollar, I promise I’ll give them $10 back.

“Everyone has a boss.” — I believe I read this in my friend Ali Kriegsman’s book, The Raise

I had seen what VC pressure had done to similar businesses in our space. Multibrand fashion marketplaces that were flooded with bad supply under pressure to grow. Taking a partnership with H&M when you’d positioned in luxury and worked with Prada and Gucci. Horror stories about the pressure to grow at all costs. At the cost of customers and employees. At the cost of the health, sanity, and ethics of the founder.

When I first started daydreaming about building this company, venture did not fit into the dream. Tight adherence to our mission, our customers, my values with zero outside influences and competing motives. I didn’t see how taking lots of money from people who may not understand the nuances of our industry or customers would ever be aligned for me.

And I got to work. I bootstrapped like a boss. It was covid and I was child-free. I had nothing to do but work and I got pretty far on my own. We operated at roughly break even and I hired a former colleague to help part-time. She busted her butt too. She had a full-time job and helped me PT. We grew. As we tripled from YR 1 to YR 2 and into YR 3, the growth rate was impressive but we were running a small business.

I didn’t want a small business. I didn’t want a “lifestyle” business. Nothing against them. But this was not a small business idea. We were building a one-stop shop for stylists, a private Net-a-Porter where they can access entire brand catalogs in one place. In order for the business to be valuable to them we had to have all the brands they need, many hundreds. In order to secure those brand partnerships, we had to have impressive sales, which means we needed all of the personal stylists on board and shopping with us. This is a dynamic every two-sided marketplace encounters and in the earliest days is called the “cold start” problem.

I needed to move faster to make this business work. And I had the ambition & resilience from years of painfully bootstrapping required to do it.

Fast = more people. More hours in the day and week than me + one part-timer could put in. I had already leveraged available capital including business credit cards and loans which are actually leveraged against your own assets (not advisable) but we had enough revenue that I could make the payments. Not predictable revenue, mind you. On a transactional marketplace, there isn’t predictable revenue as there is in a subscription business. We lived and died on each individual transaction that we took a percentage on. This created an underlying level of stress and insomnia that I grew accustomed to.

In order to grow faster, I had to raise money.

I started with a small Friends and Family round, around $100k. Angel checks from people I’d known professionally, vendor customers, and industry investors who needed a future business model to bet on as the legacy players faltered.

Now I have some other people’s money but not a lot. To go FAST, we need much more. I’m still opposed to venture but a friend-of-a-friend had built and sold her fashion-tech company and now worked as a Techstars MD. I met the NYC team and they were amazing. I wanted to learn from them. They told me going through the program doesn’t mean you have to raise more venture. (Caveat: participating in Techstars requires taking their money, which is a venture investment.)

I applied and got in. They tell you it’s harder to get into than Harvard with less than 1% of applicants accepted.

Some of their money is optional and some is not. I took only the required amount. Then I took the rest, because I needed to hire more help to run the company while I participated in the program.

I started drinking the VC koolaid through immersion in the venture ecosystem during the program, but really, the koolaid was already in my veins through the required investment. And to be clear, I took VC money eyes wide open. I had learned a lot about the repercussions and responsibilities of taking this money at this point.

For context, I am 2.5 years into the journey at this point. And I’m coming up on my 40th birthday.

I am faced with two paths. Continue growing at the same pace or take the jet fuel, see if it unlocks growth, take more jet fuel, grow very, very fast.

My dream and reality are at odds.

I want calm, stable growth with no one to answer to but my team and my customers.

But building a marketplace requires speed and I don’t have years and years to see if this will work. I am not 25 with my whole life ahead of me to start and fail companies over and over. I need this one to either work fast or fail fast. That annoying startup catchphrase: “fail fast.”

The concept worked for me. The promise of win big or fail fast sold me on the venture path.

If this was not going to work, I wanted to know sooner than later. For my team too. Their time investment means just as much to me as my own and I have a responsibility to them. I don’t want to ever be a zombie or cockroach company: alive, but not growing. No one has time to waste.

The expectation of taking VC money is that you spend it fast. You can’t hoard it and grow slowly and keep a stockpile for a rainy day. You spend what you have, you keep growing and you raise more. If you don’t grow, the money is gone and you close (that’s the fail fast side of the coin). You’re not spending wastefully. You must spend in ways that unlock growth. That is what you live and die by. Spend fast to grow fast to raise more money fast. The longer it’s been since you’ve raised, the harder it is to raise more.

For better or worse, that’s what I signed up for and the benchmarks that determined if In-Seam was winning or failing.

Subscribe + stay tuned for Pt 2: Failing fast + shutting down our marketplace. Goodbye to In-Seam as we know it :(

Here are all my resources on raising money:

Andrea Minkow Fundraising Coaching

Elevator Pitch Framework

Blurb Template

Class Rebel Fundraising 101

Guy Kawasaki Only 10 Slides you need in a pitch deck

Kelly Nyland’s Fundraising Guide

How I raised it podcast

Bootstrapping post, how i raised it posts pt 1, pt 2, pt 3

Pitch call structure

My personal financial situation that made being a startup founder possible

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

Fundraising prep + coaching

GTM & growth strategy and execution

How do you professionally identify?

I am a private client stylist and I work in shopping partnerships at Instagram. I am also a mother of (almost) two boys, which has allowed me to empathize with many of my clients’ lifestyles as well as the physical changes that they may face throughout different parts of life.

How do you work & what services do you offer?

I style clients both locally in NYC and as far as Tokyo - 90% of my business is virtual. I offer full wardrobe refreshes, seasonal outfit curation, vacation and event styling, and closet digitization.

How long have you been doing this work?

About 3 years formally, and many more informally!

How did you start?

I have always loved fashion and worked in retail and e-commerce, but several years ago I took a Jay Shetty course on how to monetize your passion. During the course he asked the question “What is one thing you could do for the rest of your life and not get sick of?” This was the easiest question I’ve ever answered – shop online. I decided to put one foot in front of another and start posting on Instagram without knowing where it would lead. I then began to style friends and family and have never looked back.

Are you currently taking new clients or booked & busy?

I have bandwidth for a very limited number of clients in May of this year before I give birth to my second son!

What’s your business model?

I charge hourly.

What other revenue streams do you rely on?

The majority of my revenue comes from the fees I charge clients. I also make commission on clothing I sell both 1:1 and on social media, either via direct brand/retailer relationships or via ShopMy.

When it comes to sourcing for your client - what factors drive your decision on where to shop from?

I have intentionally built my business so that my clients do their own ordering and returning with the exception of when I facilitate purchases on consignment.

Each client is different, and when I work 1:1 it’s important that I understand someone’s individual priorities. Some people may prefer to receive as few shipments as possible while others may need something quickly. If the same item is sold by two retailers with different prices, I will typically share the lower-priced item to build trust. In general, I also try not to recommend items that are final sale or from retailers that I have not vetted.

How important are commissions to you?

Commissions are important but trust and client relationships are more important. I will always prioritize recommending an item in my client’s best interest even if it means I will make a lesser or zero commission.

I also weigh the benefit of commission against the logistics of execution. For example, it’s great if a brand can offer me a more competitive commission rate plus the ability to purchase on consignment. However, if I am already placing a consignment order for my client on Vetir, I will sacrifice a few percentage points of commission for the ease of ordering and returning from within one platform.

How has ShopMy changed how you approach your work or revenue?

ShopMy has been incredible for my business. In addition to creating a brand new revenue stream on social media, ShopMy allows me to offer a completely frictionless affiliate experience for my clients upon delivery of a lookbook or shopping list. I have also been able to connect directly with brands on ShopMy and deepen my relationships with the market - I can’t say enough good things about the platform.

What’s a typical profile of your clients?

My clients range from women in their early 30s to late 50s with a wide variety of careers and interests. I work with Fortune 100 executives, New York Times bestselling authors, entrepreneurs, full-time moms, and brides. I have styled everything from executive summits in Dubai to couples trips to St. Barths to Good Morning America appearances to school drop-off.

What’s your craziest / proudest client moment / win?

I styled Caroline Chambers for her second cookbook to be released later this year. I can’t share the images yet but I am so excited and proud that our outfits will be forever inked in print.

Any wild or botched sourcing stories?

At the beginning of my styling journey I played around with marketing by putting some ad dollars behind my Instagram profile. One client who converted from the ad haggled with me on price and ultimately ghosted me after I had delivered her lookbook but before paying the remaining half of her invoice. I learned then that the clients paying the least would often be the most difficult to manage, and that creating a sustainable, luxury styling business would only happen slowly and organically via word of mouth.

Share a recent client look you love?

I styled a very special bride for her rehearsal dinner in a Vivienne Westwood dress, Staud boots, and a vintage silver cuff bracelet.

What brand or item are your clients loving right now?

Brooke Callahan poplin pants are my clients’ (and my) absolute favorites (they come in many colors & inseam lengths – size up!).

My bridal clients are also loving Wiederhoeft.

What brand are you loving right now that you’re hoping your clients will get into as well?

Not all of my clients are this adventurous but I’ve been loving Conner Ives for limited release upcycled ready-to-wear.

I’m also very into Australian label Beare Park for their sexy silk separates at a fair price point relative to their high quality.

What tools can you not live without to run your business?

ShopMy, Canva, and most recently Claude Code. I begged ShopMy to open its APIs (they wouldn’t) and then nearly hired an engineer to build a custom workflow to help me create client lookbooks in Canva. Fast forward six months and I built all of that for pennies using Claude Code :). It is an absolute game changer for any entrepreneur and has allowed me to scale my business so I can focus on client sourcing (the fun stuff + where my expertise lies) instead of on repetitive admin tasks.

What are you manifesting this year?

Giving birth to a healthy baby boy and finally fitting into my clothes again!

Where can people find you?
@trouvaille on Instagram and in downtown Manhattan :)

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I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

Fundraising prep + coaching

GTM & growth strategy and execution

“I’m sitting on the floor in the fitting room of <luxury dept store redacted> and I drive $250k in business to this store each year and don’t even get a thank you or holiday card (and zero commission).”

Mic drop.

If a client spends $50k / annually at a retailer they are automatically tagged as high-spend and upwards of $100k/ yr would qualify them for this retailer’s top client program which includes invites to prestigious fashion events and many more perks.

But, working on behalf of a client is perceived very differently and Allison’s experience demonstrated to me that there is a real perception problem for the hard work of the behind-the-scenes private stylists shopping for others. I could go on, but this feature is about Allison!

Allison is an absolute pro, veteran NYC stylist, and early adopter to In-Seam.

Now, she’s building her own app to scale her work beyond her private clients.

In between spring appointments, she agreed to be profiled for our first feature of Private Client Stylists you need to know which we will be posting weekly. Read more about the series launch here and subscribe for free below.

How do you professionally identify?

I refer to myself as a private stylist…and sometimes Magician.

Where can people find you?

www.stylemadesimple.com

IG @style_made_simple

TT @style.made.simple

What services do you offer?

My consultancy offers styling services for:

• General wardrobing

• Travel capsules

• Special events

• Media appearances/panels

Why do clients reach out to you?

We often first meet clients during a major life stage transition.

How long have you been doing this work?

I’ve been styling in various formats for almost 20 yrs!

How did you start?

I have a background in styling for on-camera and advertising (still photography) which has informed the quality codes of the business.

I didn’t even really know what styling was when I started my career - there just wasn’t a lot of info about it. I ended up in the Bloomingdale’s Fashion Office learning about so many aspects of the industry in 360 way - I worked in trend forecasting and supporting the fashion directors, working on fashion shows and in-store events + more. From there, I dove into on-camera styling and went to work a television show. During this phase, I realized how people could benefit from having access to this skill set. So I started building a business and trying to connect with my ideal clients.

Are you currently taking new clients or booked & busy? Do you have a waitlist?

It depends on where we’re at in the fashion cycle. Right now it’s peak season, so we do have a waitlist, but we generally move through the list quickly.

Do you work mostly in-person or primarily digital?

While we’re NYC-based and work with clients IRL and digitally, we have clients all over and do travel to work with clients.

What’s your business model?

I offer styling packages to serve projects that are larger in scope and offer hourly fees for projects with a smaller scope.

How do you think about revenue overall? What other revenue streams do you rely on?

Personal styling isn’t really scalable (which is also the beauty of it). So it can be a challenge to identify other revenue streams outside of daily or project rate. Affiliate links and commission are a great resource for an ongoing additional revenue stream.

When it comes to sourcing for your client - what factors drive your decision on where to shop?

This is so important because the #1 priority is to deliver outfits that make our clients look and feel their best. Personalization is a critical feature of my work and I take several factors into account, prioritizing:

1. Budget

2. Taste level

3. Lifestyle

4. Wishlist

How important are commissions to you?

Commission should be baked into any stylist driven transaction. After all we’re the reason the sale is taking place and that concept can be lost on brands & retailers. That said, commission never drives my decision making - finding the right piece for the client always comes first.

How has ShopMy changed how you approach your work or revenue?

I was an early adopter with affiliate platforms like RewardStyle so it’s been incorporated into how I do business for years. It’s an important feature to this type of business because it allows me to generate revenue from a broader reach of clients through newsletters, social and curated recommendations.

What’s your proudest client win?

• Styling a budding teen musician embarking on their first European tour

• Styling my first trans client

• Styling a client going to their first network up-fronts as a show creator

I especially love working on looks for special moments - from entrepreneurial branding to weddings!

What are your clients loving right now?

• TWP for polished classics like this suiting pant + bustier

• Guest in Residence knits

• The Frankie Shop cool girl vibes

• Rachel Comey for functional pieces with personality and a little quirk: shades knit jeans

• Apiece Apart - the best pants!

• Officine Generale - when you’re feeling French

• Matteau- for resort

• Kallmeyer - understated cool girl, a brand originally introduced to ME by In-Seam! That intro enabled me to pull Kallmeyer pieces for my clients and now the brand is blowing up!

• Rohe

• The Latest

What could brands and retailers be doing better to attract your clients’ business?

It comes down to relationship building. Ultimately, I want to work with brands/retailers who are going to act as great partners and make it easy for me and my clients to do business with them. This is a big opportunity that sometimes goes unnoticed.

What are you manifesting this year?

Growth and scale in ways that were never possible before! As the co-founder of www.desitnationunknown.co - a travel readiness platform (from the perspective of wardrobing, ofc) we’re excited to build a new product with AI systems to deliver our expertise at scale.

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

Fundraising prep + coaching

GTM & growth strategy and execution

Who buys this stuff?

Have you ever wondered who buys a $50,000 dress? The one you’ve seen on the runway, on the red carpet, an editorial, a global ad campaign. Marketing & PR gets that dress worn and seen, but no money changes hands.

Who will actually buy it?

Sometimes no one.

Some pieces are just for marketing & brand building, to sell you the handbag, shoes, or lipstick; others are produced and sold at full price: $12k, $50k, $80k+.

But who pays that much for a dress? No one that’s walking into a store and buying it off the rack.

The retail ecosystem is built for B2C shopping: people walking into stores and browsing online then purchasing. I’ve worked in the retail industry for 20 years and, at luxury prices, there is always another person involved. A trusted, personal relationship.

People buy things from people they trust: on a shop floor, on your feed, or in their closet at home with a private stylist.

I started In-Seam to support the relationship owners (personal shoppers, private stylists) and now I’m finding new ways to share their stories and decode the ecosystem by exploring:

• What is a private client?

• How has personal influence reshaped distribution?

• What is a personal shopper or private client stylist?

• How is their work and influence different from red carpet, celebrity, editorial, and runway stylists?

The company we built + what happened to In-Seam.

I started In-Seam with a mission to bring awareness, respect, and resources to luxury’s MVPs, the personal shoppers & stylists who drive the majority of value in the luxury ecosystem through their personal relationships with clients; a group that has never been recognized for their hard work and contributions.

Unfortunately, our business model ultimately was not able to support the needs of our customers the way we wanted. I’ll deep dive on this in a future post.

Yet, In-Seam was a successful experiment in many ways. One way is that we proved when treated like a customer, personal shoppers + stylists can drive outsized value and loyalty to a brand or retailer.

In-Seam the company is officially dissolved but my mission remains. How I execute on the mission is adapting.

What’s next.

Now, I feel called to share what I learned about our customers throughout our time building with and for them. I am driven to demystify the behind-the-scenes ecosystem for all to benefit from a greater understanding of:

who private client stylists are, how they work, what drives them, and what they need to service their clients well.

Personal shoppers & stylists need efficient access to the brands and products their clients want to wear.

Brands and retailers are starting to learn that personal shoppers & stylists are a high-value customer segment. 

The two groups need each other, and, there is a general lack of understanding of the customer segment that blocks them from coming together to smoothly transact.

Before, we built a marketplace for these parties to seamlessly connect.

Now, I hope to share information across these groups to facilitate a greater understanding and increase connection for all.

You, get to peek BTS to see what it’s like to shop like a private client. Perhaps, you’ll even become one.

Join us.

Shopgirl: personal shoppers + the secret lives of private clients will publish approximately once weekly featuring:

• profiles of the personal shopper and private client stylists you need to know

• sprinkling of explainers on how to market to this group and acquire new high-value VICs as a brand or retailer

• a few lessons learned along my journey building a VC-backed technology company

Personal Shoppers - if you’re any type of personal shopper / stylist / private client stylist / shopgirl / product-curator and would like your work to be featured, please contact me ann@in-seam.com. Follow along by subscribing for free.

Brands + Retailers - if you work for a brand or a retailer and would like to learn more about catering to private client stylists, subscribe and follow along to learn about this valuable customer segment. I’ll be sharing useful tools for you. Reach out to me with any specific questions or to implement a custom strategy.

Shoppers — subscribe and check your inbox for once weekly-ish profiles loaded with shopping recommendations.

I’m Ann!

Commercial operator w/ 20 yrs experience building businesses and tech products

Award winning ecommerce marketplace founder - created a new distribution ecosystem

Raised millions in venture capital

I work with founders, consumer tech platforms, marketplaces, and luxury brands at the intersection of product, customer, and growth. My recent projects include:

Omnichannel customer acquisition and LTV growth for brands & retailers

Customer discovery & business model validation

Fundraising prep + coaching

GTM & growth strategy and execution