The 25 Micro-Habits of High-Impact Managers

Management can at times seem like staring down a large block of marble — an intimidating task that requires the right tools. And in our experience, most management advice tends to focus on tackling the biggest chunks: assembling high-performing teams through hiring, delivering tough feedback and checking in regularly. Of course, holding regular 1:1 meetings and honest performance reviews are critical items on your manager checklist to get right — but sculpting a magnificent piece of art also relies on the finer chiseling work of shaping that rock, bit by bit. After all, it’s the smallest movements and the intricate detail work that makes a statue worthy of display in a museum. However, this tends to be overlooked.

The signs that you have a great manager are the actions you don't think about until later.

 Part of a weekly conversation where they stop and listen to the team, waiting until everyone's had a chance to share their thoughts. Or the way they pull you into conversations with support, knowing you might be taking a risk, but they always have your back. Even just the occasional overshare about their own lives to show you're all human,” says 

It got us thinking — what are the little daily habits that often go unnoticed, but when linked together add up to form an incredibly strong chain between manager and direct report? To that end, we spent the past few weeks reaching out to folks all across the First Round community for their take on this question: 

What are the small things a great manager has done that have stood out to you across your career?

What follows is a can’t-miss list of 25 targeted tactics for upping your management game — no rote training sessions required. Some folks spoke from their experience as a direct report under a favorite manager in their career. Other startup leaders we admire with tons of people management experience opened up their own playbooks. Whether you’re a brand-new manager, a seasoned vet, or have goals for taking on a management role in the future, there’s plenty of leadership development tactics for you to jot down.

To make the mega-list easier to digest, we’ve broken it down into eight categories — use the outline on the left to navigate to each section. Each category is defined by a soft skill like vulnerability and building trust, followed by a few tips to put those amorphous traits into practice, like monthly reflections or tactics for delivering feedback with care. We assembled this list with hopes that you’ll find at least a few ideas you’re excited to try out — and a greater appreciation for the micro-actions that set stellar managers apart. 

Most folks don’t intend to micro-manage — but when priorities pile up and your own boss is pinging you for updates on that encroaching deadline, the urge to take the reins from your team is hard to ignore. But breaking this habit is critical to give folks the opportunity to flex muscles that would otherwise atrophy and stop them from reaching their full potential.

“Looking back on my career, my favorite managers allowed me to own decisions, even if they disagreed with me. They couldn't do this for every decision — some were just too expensive or difficult to reverse. But if they spotted an opportunity for me to own a decision, they let me run with it. This would often be preceded by spirited debate, where they challenged my assumptions and forced me to think through various outcomes. Then they gave me the space to decide and room to fail and learn (and to sometimes surprise them),” says 

, suggests managers commit one particular phrase to memory — and use it liberally.

“I trust you, make the call” might be the six most powerful words you can hear from a supervisor.

“The best manager I ever had was gifted at coming up with big ideas. He saw incredible market opportunities and was constantly thinking of programs that would improve our offerings. 

But what made him the best was how he passed these ideas along to the team to bring them to life

. Along with them, he would share his utmost confidence that we would make them better than he ever imagined. This enabled me to do some of the most creative work of my career, and I felt supported and believed in along the way,” says 

3. Think of yourself as the team captain, not the head coach.

“I believe that healthy adults don't derive any pleasure from a ‘waterfall’ power structure.

When a manager understands their role is as a coordinator of priorities and doesn’t act from a place of authority, they typically buy into the broader concept of being part of a team with each team member equally responsible for success, trusted to do their work as adults,” says 

The best managers "ask" more than they "tell."

4. Set the tone with cross-functional partners. 

Giving direct reports the freedom to operate as owners extends beyond your immediate team — weave this thread across the entire company fabric. “Oftentimes other leaders in the company may come to me as a partner in driving a decision or initiative forward. Rather than jump right into it, I try to recommend that they go directly to one of my direct reports. I communicate to both the partner and my direct report that I'm available if needed, but that I trust my direct report to have full decision-making ability,” says 

For years in management circles, there have been larger conversations about bringing our whole selves to work and this went into overdrive once we all started working remotely from our kitchen tables (with kids, pets, and piles of laundry all front-and-center on Zoom). We’re shedding our more stoic “work persona” and 

previously weren’t on display in the office. 

 — it’s a long-overdue reckoning, and high-impact leaders need to set the tone by modeling authenticity to their team, rather than always plastering on a brave face. “Part of the reason why emotions have such a bad reputation is that we’ve tried to keep them out of the workplace for so long. 

We suppress everything we feel, which means we don’t resolve issues while they’re still manageable.

 Instead, our feelings fester,” she says. 

“Great managers demonstrate self-awareness and empathy by sharing their working style preferences and development areas. I've always appreciated when managers provide an onboarding guide to who they are as a person and a manager. This should include their work styles, expectations of their directs, values and motivations, areas of feedback they are working on and decision-making preferences,” says 

, Chief of Staff and VP of Program Management at

. (If you’re looking to put this one into practice 

outlined the importance of creating a user guide

 right here on The Review— and included plenty of examples to help you get started creating your own.) 

As Product Lead on the New Product Experimentation team at 

 has even experimented with sharing her team’s user manuals during the interview process with top candidates. “This builds psychological safety and trust and can set a clear bar for transparency and honest introspection. As people are considering your team, I’ve found this can be a great way to find alignment with potential team members,” she says.

In addition to sharing her working guide, Mohanty also implements a weekly habit to get folks on her team on steadier footing, even amidst stumbles. “When you set an example of being vulnerable, it makes space for greater psychological safety on the team. As I’ve moved through my career, I’ve learned how it’s okay to show some vulnerability — whether it’s about a personal challenge or something I’m struggling with at work. As a result, it builds deeper relationships with my reports to feel okay expressing 

 or other messy feelings,” she says. To get tactical, Mohanty suggests managers share one high and one low each week, either in a team meeting or in a weekly email, to create an atmosphere of reflection and transparency.

Failure isn’t easy for anyone to talk about — especially for managers who feel like folks are counting on them to get things right. But no one’s infallible, and 

 relies on folks feeling like they can try new ideas and fail fast. “Share a story where you've failed personally or professionally and what you learned as a result. It sheds light that we're all human and on the same level. It allows team members to share their concerns and feel like it's okay to fail,” says 

, Senior Director of Monetization and Pricing Strategy at Pantheon.

And don’t hesitate to open up about the fun stuff, too — especially when workplace stress piles up. “Share a personal update or just a quick anecdote from your life outside of the office — it doesn't have to be big or significant or detailed. Even something as simple as, ‘My son did this today for the first time and it was so cute!’ This makes employees also feel like they can bring their whole selves to work and share with team members. This is especially important in a remote world where it's a lot easier for people to feel isolated and disconnected,” says 

, there are a number of features, marketing campaigns, or sales tactics to tackle. To stay nimble, high-impact managers must strike the balance between excelling at the basics and juggling new ideas that make a splash. 

“A startup doesn’t just move fast — it moves 

, requiring a constant adjustment to how we operate to stay effective. A monthly reflection is the single most valuable tool I’ve found for scaling yourself in a fast-paced environment with continually increasing responsibilities. This is also where we establish a lot of trust and I show care for each team member, which in turn allows me to push the team harder on a daily basis without erosion,” says 

Her frameworks for speeding up your marketing engine

 is a Review must-read for marketing leaders.)

She advises setting up specific 1:1 monthly meetings with each team member, where the report reflects on the three things that went well the past month, and three things they’d like to go differently in the next month. Rezaei then shares her own 3x3. The conversation ends on a buoyant note: What are you most hopeful about as you think about the next month? 

To get started, you can borrow from her template.

When we move too fast, our development areas tend to get amplified and we gloss over our strengths and impact. Without taking time to reflect regularly, we don’t adjust our behavior fast enough — and bad patterns start to emerge and we forget to celebrate our wins.

9. Reserve time for thinking outside the box.

While you’ve likely established some sort of regular weekly check-in with direct reports, these meeting blocks can quickly get eaten up by basic status updates rather than thinking bigger. Carve out time specifically to get creative. 

, recommends setting aside time for dreaming up new ideas: “Providing regular blocks of time for brainstorming and ideating together has been super helpful to bring non-urgent matters to discuss and process and remove ‘thinking or planning’ blocks for kicking off new projects”

As an organization grows, there’s an increasingly heavy burden to 

connect the company’s vital organs together

. The high-impact manager spots opportunities to tie their team’s work with the broader goals all across the org chart. 

“The best managers provide context for executive decision-making and rationale that enables me to prioritize with a cross-functional lens,” says 

, Head of Veterinary Translation Medicine at 

. “My manager, from the very beginning, has taken time out of his incredibly busy schedule to answer questions thoroughly and find teaching moments. He doesn't just answer my specific question, he ties it into broader themes and sometimes even goes up to the whiteboard and diagrams things out. Having a CEO take the time to help me personally develop makes me feel valued and supported,” says 

As a startup grows (along with the mountain of work on your plate) regular 1:1s can seem more like rote rituals than effective meetings. But 

the very best managers approach 1:1s with great care

. “My manager listens, always — whether it's about a problem at work, a funny story about a pet, or something I’m excited to learn. In our 1:1's, they are always present and not sidetracked by performing other tasks on the side,” says Laura Percy of Truveris.  

Outside of 1:1s, there’s plenty of questions or issues that crop up — sometimes at what feels like the worst possible time. “The best managers I've worked with always make the time to talk to you, no matter how busy they are. They realize that five or 10 minutes invested immediately not only addresses the topic in question, but it also shows the employee that their needs are a priority,” says 

As an individual contributor, following through on deliverables is core to succeeding in your role. But as you move into the management track and calendars fill up with countless meetings, these good habits can begin to slip. “A small action that has a big impact is just following up and following through consistently,” says

, echoes that this is often undervalued. 

The best managers are incredibly consistent — they’re almost always on time, follow-up, and close the loop on open items. The diligence and consistency seem straightforward but are rare in a leader. 

Whether you’re a first-time manager or have a resume full of leadership positions, like the most-loved knives in a chef’s kit, your people management tools frequently need sharpening. Maybe 

 between members of your team, or your startup is hitting its stride (which comes with growing pains), or you’re 

. Tap into your empathy reserves to clear these hurdles. 

13. Don't forget the humans behind the company's goals.

“When my managers have been great, they’ve looked at my situation with compassion above all, above what they (or the company) need from me. The same goes for when I’ve been my best as a manager. That doesn’t mean the company’s priorities don’t prevail — it just means I feel acknowledged as a human being in whatever the situation is,” says 

“It’s not trivial to pull off because there’s so much pressure on a manager’s shoulders to extract value from a team (to put it in the coldest terms). There’s not often as much pressure to consider those team members in their full humanity. I’ve been fortunate to work for managers who make the experience as human(e) as it can be. I do everything I can to pass that experience on to my directs.”

14. Encourage folks to put themselves first. 

Some reports may wear their heart on their sleeve, and you can quickly decode when something’s awry. Others may have a poker face — but deserve just as much attention. 

, recommends checking in privately when you notice a report is struggling. 

, has seen great managers go a step further and gently nudge folks towards a much-needed break. “If I'm feeling overwhelmed, my manager encourages me to take time off and actively asks how she can lighten my load. These actions help me feel cared for and supported,” she says. 

And when your report is out of the office, resist the urge to ask a quick question over Slack. “If I'm sick or dealing with a personal matter and out on short notice and there's something urgent, my manager handles it. Full stop. My manager doesn't need to ping me or ask a lot of questions, distracting me from my time away — they're just able to take care of it,” says 

 is a key piece of any manager’s role — and also one of the trickiest to get right. There are all sorts of landmines that can blow without warning — even the word “feedback” can cause folks to cover their ears because it’s so rarely done right. But when approached with care, feedback nudge reports closer to their career goals.

Being a supportive manager is easier when the road is well-paved — you’re shipping your deliverables, not missing deadlines, and cross-functional partners are happy. But any startup’s path is littered with potholes and speed bumps that can quickly throw you off course.  

“Early on, my manager told me, ‘I don't want you to mess up. But if you mess up, I will have your back.’ This instilled in me that my manager trusted my decisions, was willing to help me through potential failure, and subtly applied pressure to live up to that trust. He said it once, but it was impactful enough that I still think about it when I face a new decision in my role,” says 

, Associate Director for Division Operations at 

Mistakes happen — if they don’t, it probably means you’re not being ambitious enough. That’s why 

 have become a startup mainstay. “My manager always has my back. Even if I've made a mistake, they explain what went wrong, we work together to devise a plan to keep it from happening again, and then move forward without blame. It may be my mistake, but my manager always lets me know I'm not alone,” says 

16. Create a monthly performance review action plan.

 system that’s chock-full of advice for making the dreaded process more impactful than painful. The key to his approach? Following up those annual reviews with monthly touchpoints. “After the performance review conversation, turn each of the feedback items into a tactical action plan your report can concretely work on. Then, like any project, check in on how they're progressing and share advice, coaching and guidance along the way.” 

“When I go to my manager asking for her to provide feedback on a resource or simply take a look at something, I appreciate that she challenges me to share my intent and clarify what I'm looking for in a response. This helps streamline communication and prevent any misunderstanding, and that clarity of thought is something I always remember when I’m making an ask,” says Lauren Jones of Warby Parker.

18. Take a beat before delivering feedback.

’ may have said it best: A great manager praises in public and reprimands in private,” says 

strongly suggests asking folks how they prefer to receive feedback early in the onboarding process.

Facebook’s Sunita Mohanty recommends prefacing feedback with a simple framing. “My previous manager knew it would be most impactful to give feedback right away on how I could have presented better in a review or ran a meeting more effectively. But there is also the risk of not being in a mental space where I really hear the feedback. He would do a great job of stopping to first ask if I’m open to hearing feedback and then proceeding, which made me way more receptive to whatever came next,” she says.

CELEBRATE AND UP-LEVEL THE SMALL MOMENTS.

, there are all sorts of big milestones that get attention. But for each big achievement, there are dozens of smaller touchpoints along the way worth cheering for. 

19. Look for opportunities to praise in the moment.

“A leader who recognizes and celebrates the smaller milestones on the way to a larger goal helps to keep momentum and motivation. This can be done through something informal like a Slack channel — direct reports can share milestones accomplished or even small wins and get feedback, questions, encouragement, or just a thumbs up,” says 

Jaleh Rezaei, CEO of Mutiny, is another fan of leaning on Slack for quick hits of positivity. “When I see something that I really liked, I usually will send a message to the person with a short heartfelt message like, ‘It was incredible for me to watch you shine in the meeting. Well done,’” she says. 

While Sunita Mohanty’s seen a louder approach: “Bang the drum — literally. A friend of mine loves using props to get her team fired up, like a tambourine she shakes when she’s excited about what someone says. Great managers do small things to help their teams have fun and take the work seriously while not taking themselves too seriously,” she says. 

Each individual person’s strengths are superpowers that lead to an all-star team. Find moments to recognize specific ways that each person’s superpower shines and encourage team practices around sharing gratitude for each other.

20. Spot chances to send kudos up the chain.

A “job well done” can go a long way — and it’s an added bonus if this gets surfaced to folks higher up on the org chart. “I always remember the moments when a manager goes out of their way to up-level you and give you all the credit for the success you achieved,” says 

Edwin Chau of Brex suggests specifically fitting this into the agenda with higher-ups. “Every weekly meeting with his direct reports, my manager (the CTO) has us each share some amazing things that members of our groups have accomplished recently. These team members could be four-plus levels removed from my manager,” he says. This next step is key: “My manager then sends a short, but extremely impactful email to all the folks that got mentioned recognizing their accomplishments. It's often a surprise to folks that someone many levels removed has that level of visibility into their work and is aware of their contributions.”

21. Celebrate moments outside of the office, too.

“My manager has twice now sent me a thoughtful gift out of the blue — once over the holidays and once when my son was born. Neither was work-related, but it was a wonderful reminder that he cared enough to remember the important occasions in our lives and it brought us closer together,” says 

 spoke about how he measures his team-building success using a peculiar benchmark that’s stuck with us: “As a founder, all I really try to index for is that 10 years down the line, if we were to suddenly go out and say, ‘Hey, there's going to be a reunion,’ all Persona alumni would all really look forward to seeing each other. And if that were true, I would think I've done a great job.”

The best leaders understand that great folks will move on from your team or your company for different opportunities — and take key steps to bring those hazy, long-term goals into clearer focus. 

25 Habits of High-Impact Managers

Sharp folks from across the First Round community share the small habits that great managers do, including delivering feedback with care, opening up about failure, and sending praise up the chain.  

We asked a bunch of sharp folks for the small habits that make great managers stand out, including delivering feedback with care, opening up about failure, and sending praise up the chain.

25 Micro-Habits of High-Impact Managers

Starting a Company in a Space You’re Not an Expert in — This Founder Shares 6 Lessons 

We’ve heard all sorts of analogies about the earliest days of building a startup — it’s similar to 

building the plane while you’re flying it

adds a new one to the list. “It’s like a video game where pieces of the game map only illuminate as you walk around the different regions,” he says. “

Building a startup is in some ways like staring down this map that is mostly dark — so you don’t know if you’re maneuvering off a cliff.”

, Fain is grateful that he hasn’t steered the company off any cliffs — quite the opposite. Just this week, Bowery Farming 

, making it the largest private fundraising round to date for an indoor farming company. As investors in Bowery Farming’s seed round, the First Round team was in the weeds as Bowery sprouted from just a seedling of an idea to a flourishing business that’s opened three farms so far (

) and partnered with top grocers like Whole Foods and Albertsons.

 (Fain co-founded omnichannel loyalty and analytics solutions company 

), the long climb to build Bowery started with an incredibly sharp incline. With a mission to democratize access to fresh, locally-grown food, Bowery’s indoor farms have crops stacked floor-to-ceiling under lights that mimic the spectrum of the sun, which can grow all sorts of produce all year, regardless of seasonality. It’s an exceedingly thorny business to build — made even more complex by the fact that Fain had never worked in agriculture before starting Bowery in 2014. 

The learning curve was steep, but Fain believes it was a necessary ingredient in Bowery’s recipe to success so far. “Naivety is an important quality for entrepreneurs to possess — there are no assumptions about what is and isn’t possible. 

The ability to not know what lies around every single corner is actually an advantage because it forces you to look around corners that you normally would never go towards

There’s no playbook for what we're doing here. That's both what makes it incredibly exciting and exhilarating — and it's also what makes it very difficult at times.

In this exclusive interview, Fain takes us back to how he went unreasonably deep in the earliest days of the company, and the most critical lessons that stick with him. Some he picked up from his first go-round as a startup founder, others caught him by surprise at Bowery — there’s a wealth of wisdom particularly for folks still toying with the idea of starting a company. From narrowing in on an idea with staying power, to convincing investors to climb aboard and assembling an early team, these are pages from Fain’s zero-to-one story that aspiring founders won’t want to miss. Let’s dive in. 

LESSON #1: WHEN WIELDED PROPERLY, NAIVETY IS AN UNDERAPPRECIATED TOOL IN A FOUNDER’S ARSENAL.

In the ranks of startup lore, there are scores of notable founders who built thriving businesses on the foundation of deep industry expertise. For example, 

 saw a recurring problem with companies lacking a real-time understanding of data and 

 had previously started a company in the email space. Fain isn’t one of those founders. 

“I grew up surrounded by the importance of fresh food. I like to say my mother was well ahead of her time by going to farmer’s markets and caring about antioxidants. But I did not come from a long-time farming family or work in agriculture before Bowery,” he says. “

There’s always a healthy amount of naivety that should go into evaluating any idea

. That said, you’ve got to pair that with real knowledge and understanding of the industry and the business that you’re going into.” 

Specifically, Fain looked to understand the challenges in the industry and the biggest holes that the company he wanted to build could fill. He didn’t 

, instead, he was drawn to the whitespace around agriculture and technology — and its unique challenges. “Coming from a world before that was bits and bytes and code — it’s pretty predictable. You can sometimes have bugs and problems, but you can fix them. Plants don't always act the way you expect them to act. And I think there's something fun, but innately challenging, about that sort of instability and uncertainty,” he says.

For Fain, building up that baseline knowledge started with an incredibly wide aperture. “I talked to anybody I could talk to. I read anything I could read, watched anything I could watch. There was not a ton of agtech going on at the time, 

 was the company people held up as the example of agriculture technology. So I met with a few folks at Climate Corp to try to get a sense of what they saw happening in the space,” he says. 

That broad lens opened up all sorts of company-building avenues — from SaaS on the farm to drones and satellite imagery for farming and precision agriculture, to name a few. “I really allowed myself to explore and understand everything — as time passed and I went further, my focus increasingly narrowed towards urban agriculture. More specifically, how do you get fresh foods to urban environments, and how do you do that more sustainably and efficiently?” says Fain.

When you’re looking to build a company, you start with a really wide aperture, and then as you walk down the path, you have to further narrow that aperture both against the idea and the ultimate business you want to build.

His lack of experience translated to an open mind and unbiased approach rooted in the 

I had no horse in the race — it didn't matter to me which system we built

. I had no preference for hydroponics versus aeroponics or aquaponics or building a greenhouse or having a container farm. What I was really in search of was the answer to what is the most scalable and efficient way to tackle this problem,” he says.

LESSON #2: BALANCE YOUR INPUTS FROM EVANGELISTS AND DOUBTERS. 

During this exploration, Fain met folks who got his founder wheels turning in hyperdrive. “One of the stories that I remember fondly is meeting with a Columbia professor named 

 who is thought of as is one of the really 

early evangelists and believers in indoor agriculture and in vertical farming specifically

. I had reached out to him and said, ‘Hey, I'd love to come to talk to you and just pick your brain.’ We ended up eating Buffalo wings at an Irish pub in the Upper West Side, talking for an hour and a half about how inevitably vertical farming was going to be enormously successful and the next biggest and greatest thing,” says Fain.

Yet, while plenty of these explorative conversations energized Fain, he was eager to balance the scales — particularly when it came to building a company around 

. “You have to be really cautious of not falling victim to confirmation bias. While you're talking to people who are both excited and generally believe in what you're doing,

 it’s equally important to find people who don't believe in what you're doing, think you're taking the wrong path and ultimately think you're making a mistake going about this business

It started with a subtle shift in framing. “The tack that I took with Bowery was not to believe this idea 

 belief wrong, but actually the opposite. I went from a base level assumption that this 

That meant for every conversation nerding out with someone like Despommier, Fain reached out to a naysayer. “I paired that with a set of professors up at Cornell who had done a lot of research and felt that it was impossible, and I spent an equal amount of time talking with them to understand why they believed what they believed,” says Fain. “There should be hundreds of reasons 

 — that’s fine. It doesn’t mean you don’t do it. But it’s better to know them ahead of time.”

It’s important to look at all sides of the equation. To think through all the things that could go right, but equally, and maybe more importantly, all the possibilities that can go wrong. If you haven't done that as an entrepreneur, you're not asking enough of the tough questions and you're not looking hard enough at your idea. 

LESSON #3: RIGOROUSLY ASSESS FOUNDER/MARKET FIT TO STICK WITH AN IDEA FOR THE LONG HAUL. 

While an agricultural novice, Fain wasn’t a stranger to the twists and turns of being a CEO and founder. After helping build up iHeartRadio, he struck out to co-found CrowdTwist in 2009 — which assembled big logos founders would dream of like Pepsi, Sony Music, and the Miami Dolphins. But the company’s success wasn’t enough to keep Fain energized by enterprise software, and he left as CEO in 2014 (CrowdTwist would 

So in the earliest days of dreaming up Bowery, he was particularly rigorous in assessing ideas with a long-range lens. “SaaS on the farm is a great business. Precision agriculture is another great industry. But they didn’t capture my passion, my imagination and my enthusiasm. That component of the stew is incredibly important when you’re founding any business, because of how long and hard of a journey building a company really is,” says Fain. 

He wasn’t the only one who had felt the 

. “I’ve seen friends get incredibly excited about an idea. They go out and they raise some money and then very quickly the excitement sort of evaporates. And now you’re stuck building this company that you’re only moderately interested in. As I was looking at and evaluating different ideas, even when I got more and more excited, I paced myself. It was critical to keep turning over other rocks,” says Fain.

I wanted to make sure that the excitement for Bowery grew and grew over time. That in the great times, and in the difficult times, my passion, enthusiasm and real love of the problem and the business would persist.

While rookie founders may hyper-focus on the starting line — from finding 

, and building out your team — in that rush to get off the blocks, it’s easy to forget it’s a marathon, not a sprint. 

“The core question you should be getting to is, ‘

Am I going to be excited about this in three years, in five years in seven years?

’ Because I knew the journey that I was about to embark on was not a short journey. What we're building at Bowery is a generational business. It is the next great food and agriculture company. And that's not something that happens over the course of a few years,” says Fain.

LESSON #4: YOU CAN LOWER YOUR CLIFF-TO-JUMP RATIO, BUT YOU STILL GOTTA JUMP. 

While Fain’s a big believer in the power of rigorous research, he was conscious of not spending 

. “We did a lot of work early on, even before we raised a dollar of capital, trying to do the best we could to understand whether the critics were right or the optimists were right. We hit the point of diminishing returns — research, testing, building growth systems and analysis and spreadsheets weren't going to yield equivalent value. The next step for us was to build a farm of some substance and size,” says Fain. 

One of the things we say at Bowery is getting ahead means just getting started. 

It’s a mindset he picked up from when he first waded into the founder waters. “Before I started my first company, I spent enormous amounts of time evaluating, evaluating, evaluating, saying no, and evaluating, evaluating, evaluating, and saying no. And in hindsight, I look back and say, ‘Wow, I said no to some great ideas.’ I spent way too much time getting to the wrong answer, arguably,” says Fain. 

It was time to step into the ring. “I could sit on a chair and think my way around this problem for another decade, but 

when building a company, you never avoid that moment where you have to jump off the cliff.

 In some respects, what you want to try to make the cliff-to-ground ratio as small as you can. But there is no amount of work and research that avoids the fact that at some point you're 

For most founders, taking that jump means starting with 

. But compared to other ideas, Bowery Farming required an immensely complicated MVP. 

“Bowery is a particularly interesting case study because it's a really complex business with a lot of components. The MVP of a software company is ultimately going to be a lot simpler in some respects than what we built as our equivalent MVP at Bowery,” says Fain. “What I did, and I think what any entrepreneur needs to do early on, is determine what matters most at that very early stage. What are the most important things for you to prove to yourself, to prove to the market and to prove to the investing community (if you're going to be fundraising)?”

The next step is identifying the most efficient paths to reach those early indicators. “What do you need to build? What needs to be created? Who do you need to hire to actually achieve those proof points? Not too much more, but not less,” he says. 

Fain built an incredibly simple framework to bite off the business into manageable pieces: Build It, Grow It, Sell It. “It meant, could we in fact build an indoor farm with the technology and the approach that we had created? Could we then grow food in the way that we expected? And once we grew that produce, would it be any good and would anybody actually want to buy it? And those seem like such simple concepts when you lay them out this way. But the work and execution underneath each layer were immense,” he says. “That framework at least gave us guiding posts to focus our efforts to determine what we do and don't do in those early days — to build and grow as efficiently and effectively as possible.”

That meant finding warehouse space for Bowery’s first indoor farm and crafting a lightweight version of what would go on to be called BoweryOS. “It’s the central nervous system and the brains of the growing side of the business, as well as the entire operations and supply chain. It was my core belief that the operating system was key to generating maximum scalability — it’s as important as the growth system itself,” he says. BoweryOS measures millions of data points from a network of sensors across the indoor farm, including humidity and temperature, that have a massive impact on the final taste. 

But while Bowery’s MVP may have been robust to account for the complexity of growing crops, Fain is clear that it was still very much a scaled-down version of the grander vision. “The operating system that we built years ago is a fraction of what we have today, of course. The farm today looks drastically different than the farm we built back then. It was all about focusing on what mattered most within each pillar of the business,” he says. The company emerged from stealth in 2017 with six different products — arugula, kale, butterhead, basil and two blends. 

LESSON #5: BECOME AN EVANGELIST FOR THE HOW, NOT JUST THE WHY. 

On top of an intricate MVP, Fain was facing an uphill battle from a fundraising perspective. “There is no crib sheet that investors can pull out to say, ‘Here are the eight questions I've asked in the past to the other hundred companies that do what you do to help me understand how to think about what your business, your progress and your opportunity,’” he says. 

Unless folks work in the industry, agtech has all sorts of nuances that are easily glossed over. “One of the mistakes sometimes people make when they look at indoor farming broadly is grouping the category into one. Sure, everything sort of ultimately falls under the umbrella of controlled environmental agriculture, whether it's a greenhouse or hydroponic growing or aeroponic growing in a vertical farm or container farming. But the truth of it is every one of these growing methods is very different from one another,” says Fain. “The system itself that you choose and the way you build your farm has an extraordinarily large impact on what you ultimately can grow in terms of your varieties, the efficiency by which you can grow those crops and ultimately how economic of a model you actually can build.” 

 — convincing all sorts of folks, from investors to employees to customers, to buy into the vision and why it’s important. But Fain adds an additional layer. “One of the important jobs that I had was being not only an effective evangelist for 

 it's important. But equally as important was being a very effective teacher to explain that 

 we are doing it at Bowery is the most efficient and effective way to tackle this problem,” he says. 

But with limited time in front of investment partners, capturing their imagination quickly is critical. “I needed to tell someone the high-level story of why what we’re doing is exciting and interesting. I also needed to explain why we’re tackling this problem the way we’ve chosen to tackle it — and why they should believe this can become a very large, successful company,” he says. “You have to be able to double- and triple-click down. And that helps people who don't know a ton about agriculture, let alone urban agriculture, get comfortable and confident in what we're building and how we're building it.”

Eventually marrying the how and why became Bowery’s brand story, and Fain took his message from Sand Hill Road to the end consumer. “It was interesting because I had people saying, ‘Why would you build a brand? That's silly, you don't need to build a brand yet. Nobody knows you guys are. Don't spend that money,” he says. 

But Fain was convinced that it was worth the investment even in the earliest days. Here’s why: “Food is changing. 

People are asking where their food comes from

. How was it grown? How was it made, what are the ingredients? What are the chemicals that are grown in my product? Who's growing it? These kinds of questions are being asked with more intensity and vigor than ever before, and they are causing a real structural shift in the food system,” he says. 

“And in many cases, structurally the system isn't set up to adapt to that change. You've got a very complex supply chain that involves many, many different players. And therefore, to answer the questions where does my food come from, who grew it? What did they grow with? It's very difficult,” says Fain.

He points to an example. “When you look at some of the recalls that have happened in produce, like romaine lettuce, at points they've recalled all romaine in the entire country because they don't know where the problem came from in the supply chain. It is almost impossible to trace back, certainly impossible to do it quickly, he says. 

So even though there were mountains of work to be done — from building the farm to creating the operating system that would manage the growing cycle — connecting consumers to that story was at the top of Fain’s to-do list. “The benefit that we can provide at Bowery is we control the entire process from seed to store and so we can tell you everything about the product that you hold in your hand. The ability to tell that story to consumers was our competitive advantage,” says Fain.

LESSON #6: FOCUS WINS THE DAY, SO STAY INTENTIONALLY SMALL. 

Despite the complexity that lay ahead, when it came to assembling the pieces of Bowery’s early founding team, Fain intentionally stuck to a small team of five. “This was such a vast problem, there were so many rabbit holes one could fall down that were interesting, exciting and felt important. 

But when there was essentially one person responsible for each area of the business, it forced each individual to only focus on the things that mattered most

I'm a big believer that focus wins the day when building a business. And certainly focus is critically important in the earliest stages because you have limited resources, limited time and lots to prove. So one of your jobs really early on as a founder is to evaluate what matters most to the business you’re building.

He started by identifying the gaps using a very simple matrix. “Where am I strong? Honestly, where am I not strong? Where do my skills overlap with what matters most? And in the areas that I don't overlap, then it's my job to go find people who can cover those areas. I come from a marketing and business development background, so I know how to tell a compelling story and build partnerships. I'm certainly not an agricultural scientist, nor am I a mechanical engineer, and I'm not a software engineer. So those are three key places where we brought folks in early on who could lend their expertise,” says Fain. 

Rigorous focus was critical, but by keeping headcount low, Fain also had an eye towards clearing what he expected to be one of Bowery’s largest hurdles. “From the financial component of our business, we have had a real focus on unit economics from the earliest of days. And that's because when you're building a software business, nobody has a question if you can make money building software — that's a pretty tried-and-true principle. The question is will anybody want to buy the software that you make,” he says. 

“In our instance at Bowery, it's actually the opposite. There's no question that there was enormous demand for better quality, better tasting, and more sustainable produce. The question was, could you do it in a way that was economically viable? And that was really where we spent all of the effort and energy early on,” says Fain. 

To challenge the status quo, you’ve got to understand why it exists. 

You’ll notice a return to the naivety theme — in his first hires, Fain wasn’t on the lookout for folks who had racked up decades of agricultural experience. “Our mechanical engineer Brian had worked in and around agriculture and greenhouses for a while, and he had some really valuable domain knowledge. But you couldn't look at us and say, ‘Oh wow, they have a bunch of experts.’ We didn't have a 20-year greenhouse grower. And that was really purposeful. That was where the naivety component of the equation came in,” he says. 

I felt it was very important to have enough working knowledge on the team to be valuable, but not so much knowledge that it would send us down the long-term prescribed path that many before us had followed.

To bring in that deep industry expertise, he turned his attention to assembling Bowery’s 

. “It’s equally important to augment the understanding and expertise (or lack thereof) from the team with really strong advisors, who oftentimes do come with decades of experience with incumbent food companies or indoor growing or operations or with grocery and retail. And that provides enormous leverage for myself and for the team in a very efficient way,” says Fain.

He sketches out an example: “I’ve always believed that what we’re building at Bowery is more than just a CPG brand — it's something larger and broader as an organization. And so I was reticent to bring somebody on with a deep amount of CPG experience alone. However, I also knew that, like it or not, we were selling a consumer product in a retail store. And so there are elements of what we're doing that mimic what traditional CPG has been doing for decades, and to ignore that would be foolish,” he says.

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