Orchard Street | They got Tinder to swipe right, Substack to find its voice, and now they're writing checks.

Happy New Year!

I still haven’t made a vision board or wrote out any resolutions for the year. Honestly, I’m giving myself this first month just to experiment how I want to spend my time on a daily basis. I started Manifest: Dive Deeper and literally couldn’t speak to this prompt:

Describe when you felt most content, fulfilled, and at peace. What were you doing, who was around you?

I know everyone says to take some time to reflect but genuinely I don’t think most people can speak to this…like it takes a lifetime to really know. Maybe I’m just the odd one out.

I think what did end up being a cause of a lot of stress, anxiety, and less contentment last year was easily getting overwhelmed and self-sabotage. I someone got in my head that I need to be the person that has their shit together in a very specific and unrealistic way. This year I want to just do, be consistent with whatever I do try out, be realistic with my time. More importantly, I want to spend more time just learning about stuff. I spent way too much time online last year. I wonder how much my perspective and voice could be developed if I just read more or acted on my curiosities. The first book I’m reading this year is Viewfinder: A Memoir of Seeing and Being Seen by the legendary director of Wicked (Jon Chu).

Alex Daly is the founder of comms+ agency Daly and co-founder and GP of Orchard Street. Called a “guru,” “whiz,” and “wunderkind” in publications such as Fast Company, Business Insider, and Creative Review, Alex has “an innate understanding of what motivates people.” She is a Forbes 30 Under 30 honoree, the industry’s “Crowdsourceress” (and author of the book of the same name), and a frequent speaker at events for designers, innovators, and big thinkers.

Ally Bruschi is the managing director and partner at Daly and co-founder and GP of Orchard Street. Passionate about building resilient, stellar teams, and creating impactful comms strategies for the companies, products, and people that inspire her, Ally leads Daly’s growing Comms and Marketing arms and manages its evolving, culture-forward company ops. Before joining Daly, Ally worked as a book publicist at Penguin Random House and a freelance writer.

What childhood hobby or interest of yours would most surprise people to learn and become unexpectedly useful in your career? I'd love to hear how it influenced your path to founding Daly and now Orchard Street.

Ally Bruschi:

Growing up, my mom used to call me “Reader Rabbit”—I always had my head in a book, and to this day, I still prefer reading to most any other leisure activity. This initially led me to an early career in book publishing, but I quickly realized that my passion for the written word could (and should) extend well beyond the siloes of the publishing world. When you read a lot of varied material—fiction, memoirs, short stories, epic novels, self-help—you internalize not only how to write clearly, effectively, and compellingly, but also the different stories and perspectives that make up the human experience. I wholeheartedly believe that being a lifelong avid reader has made me a better and more empathetic communicator, which has in turn made me a better publicist, team manager, and leader. 

A big part of our thesis with Orchard Street revolves around the idea that most startups spend so much time obsessing over the product and not nearly enough time honing both the internal and external comms needed to show why a product matters. Every founder has a story to tell, but not everyone knows how to tell it—and people who can help you shape that story towards your desired goals are invaluable to the success of your company—no matter the category. 

Being able to communicate clearly & effectively is a true superpower—and most early stage founders could benefit from having a Reader Rabbit on their team. :) 

Could you paint us a picture of Daly PR's evolution—from its inception to today? What was that transformative client project that helped define Daly's unique voice in the industry? How do you envision Daly and Orchard Street amplifying each other's impact? 

Alex Daly:

With a background in journalism and documentary films, I began launching crowdfunding campaigns to raise money for the films I was producing (and picked up the nickname The Crowdsourceress along the way!) Creators started coming to me to craft their story, launch on Kickstarter, and tap into the brilliant power of communities for funding. 

One of those creators was one of my most transformative clients to date, Neil Young (for his $6.2M campaign); but the exciting list goes on, including the producers behind the first documentary about writer Joan Didion; musical sensation TLC; Standards Manual’s NYCTA & NASA reissues; Freitag’s first-ever travel bag; media artist Scott Thrift’s MoMA-bestselling clocks; and more. 

During this time, I raised over $25M across hundreds of campaigns, and crowdfunding clients began asking for ongoing PR support to help sustain that impact—that’s how Daly was born.

After launching Daly in 2019, I brought Ally on to support on the PR side (Ally had spent 5 years as a book publicist at Penguin Random House). In joining Daly, Ally quickly expanded beyond her publicist role by proving her strengths as an operational superstar—becoming a Partner at Daly in 2021, and working with me to responsibly grow Daly’s team from 3 to 12, and increase revenue by 200%. 

Then, in 2023, we rebranded Daly as a comms+ agency. We had been aware that the old way of PR hadn’t been working for a while, and decided to act on the growing sense that they needed to start doing things differently. Now, Daly offers highly customized, cross-category support that helps its clients truly stand out and shine—including everything from launch comms to ongoing media relations support, to affiliate marketing, brand repositioning, intimate media event strategy, micro-influencer campaigns, and much more.

This pivot also led us to thinking about the full flex of “comms+”––if we were going to really take a holistic approach to comms, that should include another important element to a company’s growth: funding. Hello, Orchard Street! 

Walk us through the 'aha moment' that sparked Orchard Street. How are you translating your vision of integrated comms, ops, and culture into tangible founder support? How do you evaluate a founder's potential to execute across all three pillars? We had a really exciting launch.

Alex Daly:

Early stage startups spend so much time obsessing over the product and not nearly enough time honing both the internal and external comms needed to show that a product matters. Because of that, when it’s finally time to launch, these companies end up looking and sounding like something we’ve seen before. They introduce themselves to the world with the same growth playbook, launch headline, uninventive culture perks, and a tired mission statement about “disruption.” 

This is the moment of truth when most startups stumble and never recover. As a team that has leveraged comms and culture to transform hundreds of companies’ success tracks, we’ve seen this critical mistake being made countless times. Companies that make it past the launch stage have to come to people like us (and spend tons of money) to build the reputation and culture they really needed from day one. 

At Orchard Street, we’re offering venture studio services and/or angel checks with intensive strategic advising for early stage founders who need hands-on guidance through the crucial, foundational decisions that can shape the path of their success. 

Need to tap into our years of fine-tuned, organizational and cultural docs, processes, and manuals? Get launch announcement support? Introductions directly to journalists? We are that hands on: your true accountability partners across comms and culture.  

As self-taught VCs building a fresh perspective in the industry, which traditional VC term or concept feels most ripe for reimagining? How would Orchard Street reframe it?

Ally Bruschi:

There are truly so many—jargon runs rampant in the VC industry—as with the PR industry, and many others! I’m convinced it’s a gatekeeping tool to keep the industry seeming mysterious and exclusive in a way that keeps newcomers out. 

But I digress!

If I had to pick one term to overhaul, I’d go with “cap table.” Because it’s not just about capital anymore, especially at a time when it feels like there’s less of it to go around. Founders aren’t just looking for checks—they’re looking to build a community of experts that’s going to help them bring their idea to life. I think we’re entering an era of VC in which the value of an investors’ time is going to be considered in tandem with their check size..

How are you thinking about portfolio construction across investment stages, average check size, and sub-sectors across the future of work? 

Ally Bruschi: 

We describe our model at Orchard Street as a venture studio meets angel investor. 

We’re currently focused on pairing small, angel checks with deep strategic, hands-on operational guidance for early stage (pre-seed & seed) companies that are innovating under the expansive umbrella of “future of work.” While this primarily means workplace-shaping SaaS tools across industries, we’ve met with early-stage founders that are building tangible products that fit the bill, as well.

Why workplace? The modern workforce is evolving before our eyes, due to the combined impact of AI, the economy, generational cultural shifts, and more. Orchard Street invests in the companies that will usher in the workplaces of the future — especially within industries like communications, design, HR, healthcare, and retail. These are the tools that will help the next generation of brands stay ahead of the curve with the way they are servicing the contemporary workforce. We’re experts in what it takes to create a sustainable, scalable workplace, and our portcos will benefit from that — culturally, and financially.

Something we’re excited about is the way that Orchard Street is allowing us to get involved at a much earlier stage than we can with our comms agency, Daly. While at Daly, we focus largely on consumer & design comms for post-launch companies (from startups to legacy companies), with Orchard Street, our model means we can  get involved way earlier, helping founders build a solid comms and operational foundation from the very start, rather than coming in way later in the game and having to correct earlier issues.

You used the founder of Notion as a great example of someone who changed culture within an industry by “moving product and people.” Who's a female founder in the future of work space that embodies this same powerful combination?

Alex Daly: 

We have been working with the brilliant business coach Holly Howard for years, and I can say without a doubt that Daly would not be where it is today without her guidance on all things workplace, operations, and culture. Based on her years of experience, she is currently working on a very exciting and comprehensive platform that reimagines entrepreneurship in the creative economy that I am jazzed about. Watch this space…! 

What unique channels or methods are you exploring for sourcing investments? If you've made your first investment, what about that company made you invest? What early signals suggest a founder will be strong in culture-building?

Ally Bruschi:

At Daly—and now with Orchard Street—we’ve always been about relationships-first approach to achieving our goals—whether that’s new business growth, talent acquisition, building out our media networks, or really anything. We’ve made so many of the connections that have gotten us where we are today by doing what we (mostly Alex) does best—gathering people IRL through intimate dinners, cocktail parties, small group networking gatherings, and more, with the sole goal of, encouraging the cool, smart people that we know to bring other cool, smart people they know, to gather, mingle, chat, and learn—thus organically expanding all of our networks in a meaningful and lasting way. 

We’ve applied this approach to expanding our investing network across fellow angels and VCs, LPs, and potential investments alike. And as we’ve grown those networks, we haven’t been afraid to ask for help and guidance from those who have been doing this for much longer than we have! A little bit of honest vulnerability can go a long way when getting into a new field. We’re not afraid to let our green-ness show, in service of learning everything we can to help our portco founders in the most impactful way.

If you were to write a piece about building an abundance mindset as a founder while also building a company culture that has healthy work/life boundaries, what would be the top three practices/habits NOT to implement? 

Ally Bruschi:

This one was a bit of a brain teaser! If you’re trying to build a company culture that permits healthy boundaries for employees while also creating a deep sense of community, you need to create a foundation of connectedness and trust that allows people to show up in their own way. 

With that in mind, I would avoid: 

1) Any mandatory social / bonding activities that happen too regularly and outside of work hours (i.e. post-work happy hours, team-building offsites, etc)—creating the space for people who want to opt in to do so can be great, but making these types of events required makes it unlikely that employees who are giving up their free time to spend additional time in a workplace setting are going to feel any more connected than they were before! 

2) Micromanaging—it can be jarring to grow your company and realize you no longer have eyes on every single thing that’s happening. Allow yourself to relinquish the need for control, and trust the smart people you’ve hired to get their jobs done. You have to trust the team and systems you’ve built, or you’ll get in your own way.

3) A culture of nice—leading with grace and empathy feels especially important in the midst of several years of economic, political, and global turmoil that impacts companies and workforces of all industries and sizes. But leaders should not be afraid to give strong, clear guidance or feedback when it’s in the best interest of their employees (or clients, or portco founders) to hear it. Because a culture of “nice” isn't actually kind! It’s often confusing, and unproductive. Be direct, be clear, be empathetic. 

Looking at the broader investment landscape, which female angels and GPs have charted paths that resonate with your vision for Orchard Street? What elements of their approaches particularly inspire you?  

1) Kelley Arena of Golden Hour Ventures for brazenly believing and investing in women;

2) Anna Whiteman of Coefficient Capital for bringing a level of pizzazz that’s seriously lacking in the space;  

3) Christine Choi of M13 for obsessively caring about the immense value of brand.

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