In recent years, there has been a rise of women in commercial real estate. This is a trend that shows no signs of slowing down. There are many reasons for this, but one of the most important is that women are simply more capable than ever before. Back in April, Women in PropTech let me curate my own panel about the Rise of Women in Commercial Real Estate. The panel was a big success and we even had a number of men attend. There were so many golden nuggets shared from some of the most influential women in commercial real estate that I want to make sure this conversation is documented and shared with the world.

First, if you don’t know already I created a list called “Otso’s Most Influential Women in Commercial Real Estate” and this list unexpectedly evolved into a movement raising women up in our industry. I brought four powerhouses from our industry onto this panel with me and we addressed some big topics.

The four women on my panel were:

1. DeLea Becker, Owner/Founder Beck-Reit Asset Management and Brokerage
2. Carrie Bobb, CEO hellojenny
3. Poonam Sharma, Founding Partner, Arden Digital Ventures
4. Melissa Swader, President, Ruby Red Media LLC and founder of Women in Commercial Real Estate

Our first topic was about timing. Timing plays a pivotal role in everything and Carrie Bobb feels like right now is the best opportunity for women empowerment. She says there are three glaring problems 1) our industry is late to pretty much all things technology 2) our industry is aging out — less than 4% of our industry is under the age of 24 and 3) we have zero market share in these digital spaces.

So why now? One reason is speed to market — “if you catch the current you could, quickly to scale,” Carrie explains. The younger generation will have opportunities to get into CRE that the older generation did not have. The early career looks a little different and they are navigating new terrain but if they can adopt tech their trajectory will be much faster. Overall, technology is enabling a lot of change and whoever can capture it at a large scale will dominate for decades.

The next topic was about what men can do to empower women in the industry. Poonam Sharma pointed out that when asked the question it feels more like a “well-intentioned favor she needs to be thankful for rather than making a wrong situation right.” Instead, she encourages men to not frame it as what they can do for women but rather address the problem from a management perspective so you are creating an environment where nobody feels like they could not bring something forward.

Two things 1) have a culture where the managers in your company (directed by the CEO) have a responsibility where nobody gets cut off and all voices are heard in a meeting; and 2) have a rule where nobody comes into a meeting without saying something to encourage collaboration and new ideas.

Melissa Swader started the group Women in Commercial Real Estate which has now grown to hundreds of women across the country meeting monthly to help each other with business. She stated that this group proved to be a ‘safe place’ for women to feel heard and ask questions or solicit advice they would not otherwise feel comfortable addressing in their own workplace. As a result, there has been a lot of collaboration in business and a number of success stories of these women helping each other. By the way, men also attend the calls and are extremely supportive.

Poonam also pointed out that the evolution of women groups is different than before. “It’s become where we are transactional, but we’re in transactional in a way that some may not see clearly. I can see a unique lens to see another woman’s awesomeness more clearly and I want to help her because she impresses me.”

We moved on to the topic of addressing the fact that some women often don’t want to relate their successes to gender-breaking barriers. DeLea Becker took this topic and stated that “if I don’t give weight to how far some women have come because of those incredible women and men that came before us then I don’t feel like I’m being grateful and gracious towards those efforts.” She pointed out that a great example of what men could do for women is what Ken Ashley did by creating his own list of influential women. “He now has fans all over the country and will get good out of it.” She added that, in general, women have to work harder from simply getting ready in the morning which is typically a larger feat than our men counterparts. “Look at me and a man that has been in brokerage and you think we’re equal then you are wrong. I have had to work a whole lot harder, smarter, louder, when to shut up and when to be loud that men don’t have to fight against.” DeLea also acknowledged her privilege as a white woman as opposed to women of color. “I hope that I can do the same for disadvantaged people (women, people of color, etc) coming up in the industry as those that have come before me to crack open the door for me to enter.”

We concluded our session with the topic: So what can we do to raise women up in the industry?

Poonam — look around you and remember that everyone needs to feel seen and if you are the one person that does that for someone you have no idea where that will ripple.

Carrie — it’s the little things, not the big ones. There’s a real big difference between expressing empathy and actually having it. I think managers oftentimes go down this path and they try to express things the way they are ‘supposed’ to express but you can tell if someone actually cares about you. People can see right through someone who has an agenda. Carrie added advice she would give younger people in the industry would be “you have to do things differently — it’s a great risk to do things the way they have always been done than to take a chance and try something different.”

Melissa — have someone who can listen that can help you get through and who wants to genuinely support you.

DeLea — be loud, be humble, share experience, share strength, and hope. Last but not least, share your failures! All of this builds relationships.

You can view the full panel discussion here.

*Special thanks to the Women in Proptech Founder, Nikki Greenberg, for inviting me to curate this panel.

Last year, I had a professional awakening. I realized that as a woman in a male-dominated industry, I have to do more than just be successful. I need to be an advocate for other women and doing so has created a positive transformation in my life and others. Women empowerment is not only about achieving our own goals; it’s also about working together to create a society in which all women have the opportunity to succeed.

In reflecting on how I used to feel about being a woman in a male-dominated industry I recall the thoughts I had as a small percentage of women entering West Point: “there aren’t many spots available for us” or “we’re competing against others because there isn’t enough room” or “I need to just blend in.” So often we’re pitted against each other because “there’s not enough room at the top.” I now realize these thoughts were all wrong because while I was successful, there were others that were struggling around me I could have helped. The higher the numbers of women who are successful brings more meaningful change and encourages other women to follow rather than just a few of us making it through.

Women have always been strong, but now it’s time for us to be unapologetically powerful. For me, it all started with a list. I’m in commercial real estate which is comprised of mostly white middle-aged men. For international women’s day last year, I decided to create a list of influential women in my industry. As I did some research I noticed existing lists highlighting women were mainly regionally based and not very diverse. Plus, I could not find any lists that combined women from the transactional and technology sides of my industry. These two sides of our industry are pretty segregated and, in my opinion, this is why innovation and adoption of new solutions are extremely challenging. So long story short I researched and developed a list of 25 impressive women who 1) from both the technology and transactional sides of our industry; 2) influential leaders committed to women activism or community; and 3) half were women of color or part of minority groups (LGBTQ+). We published our list on international women’s day and were overwhelmed by the support from the industry.

I had no idea the degree of impact that list would make on my personal life. I hosted an online meetup inviting all 25 women to meet virtually. I assumed it would just be one meet and greet and then everyone would go their separate ways. The vulnerability, respect, and empowerment on that first call were powerful and I remember feeling almost blissful and seen afterward. It was enough to make me want to coordinate a quarterly virtual meetup which ended up increasing to us meeting monthly. I realize I was not the only one that felt that special energy after we would finish our calls (which almost always go over the allotted hour) — each of us described it as ‘magical’ so we properly named our meetups “Monthly Magic Hour” and we felt it whether there were ten women on the call or just three of us.

What’s super special about our group that meets regularly is the degree of execution and assistance we provide for one another. How do we do it? At the beginning of every meeting, each woman presents an ask of the group. I decided to structure this into our meetings because as women we are generally reluctant to ask for help. So when we have our meetings, our asks must be actionable. It turns out when you have a group of women who bring actionable asks but also want to genuinely see others succeed, the sky is the limit. We have done deals together, supported in sponsorship dollars for other women events, put each other to present on some of the biggest stages in the industry.

A few months into our meetings, I woke up one day feeling different. I felt more confident and more supported. This was a feeling I had not felt in a very long time and I realize I did have a great support system earlier in my career. When I reflected back on my days at West Point and in the military I realized I had my core group of women friends from the beginning. We helped each other survive to graduate West Point with tips on which classes to take, which guys to avoid, and how to wear our uniforms (designed for men). Even after 25+ years, we are still family to one another. I didn’t realize how special having a woman tribe was until I left the military and felt isolated in another male-dominated environment where women were more segregated. I didn’t have a tribe until I met the women on the list I started.

Eventually, women in the industry were starting to reach out to me for advice. They started reaching out about my experience being a woman in male-dominated industries, and what I thought of their ideas on how they wanted to bring change. There was also an increase in women messaging me feeling like giving up because it felt too hard being a woman in this male-dominated industry.

I am proud to say that these women who reached out have found success after our talks when they may not have otherwise given themselves another chance had they not reached out. Women are so brilliant and multi-talented; but especially in industries where there are so few of us, they need the support of other women reminding them that everything is possible with confidence, perseverance, and a willingness to ask for what we need. Women are trained from early on to not take up space; that is why women don’t apply for jobs unless they meet 100% of the qualifications while men will apply with 60–70%. Women also earn less than their male counterparts even if it’s the same job.

We have come so far but yet still have so much further when you look at these statistics:

• In 2021, only 2.3% of venture capital money went to women-led businesses.
• Women makeup 51% of the population but only hold 26% of all seats in Congress
• Only 21 CEOs leading Fortune 500 companies are women
• Women make 81 cents to every dollar that a man makes even if they have similar educational backgrounds and experience levels performing the same duties as men do.

This list can go on. These numbers will only improve if we are dedicated to raising each other up. It’s also extremely important to have men as allies raise us up as well. I’m very lucky to have two extraordinary male co-founders who embody the qualities of supportive male allies and believe diversity makes teams stronger. So, if you are a woman feeling alone in your industry please reach out — I’m here for you.

The colleague I was speaking with laughed as I told her “it’s important to me that every person on my team finds joy in the role they play.” She explained, “are you telling me you actually feel joy with work? It’s one thing to feel motivated and satisfied with work, but I’ve never equated it as high as an utmost feeling of joy.” I could see where she was coming from — the life of an entrepreneur is hard and most would not consider themselves feeling ‘joy’ until they reached their goals or sold their company. I used to think the same thing — entrepreneurs make a lot of sacrifices (financially, personally, in our relationships) thinking it will all be worth it in the end. As I reflected on that perspective, it dawned on me that if 95% of startups fail then where do those sacrifices go? Are they worth it? I’ve written before about how I manage my mental health but what I want to share in this article is how I’ve found joy in both my business and personal life.

Earlier this year, I realized that I personally tend to put my mindset in this mode of “suffering” which means doing fun stuff or feeling happy would internally surface feelings of guilt…because I’m supposed to be suffering until I get to my [enter goal here]. We live in a society of people that feel valuable when they say “I’m just swamped” or “I’ve been working until 2 AM every night this week and the weekends.” I’m not saying that you should never work hard or put in the effort to achieve your goals. I’m simply suggesting that you question how happy you are during the process. Because if you’re not happy in the process i.e. the present, then what’s the point?

Also here’s the thing, when you’ve sacrificed everything else in your life for your business and the business doesn’t work out then what do you have left? My last two grandparents died this year and one left me with the advice I will never forget. My grandfather told me, “whatever you are worried or stressed about today, it won’t matter when you are my age (85 years old).” There’s no better reminder to fight for happiness in life than when you experience death around you. Why waste your energy worrying about things that won’t matter when you die? I realized I needed to change my perspective and not live every day in fear worrying about what others may think of me or what could go wrong in life. I needed to take a step back and notice…notice what activities bring me joy and double down on whatever those are.

So how can you find joy as an entrepreneur? Here is what is working for me:

1) I’m sitting in the best role I can play for my company. I started out leading the company where I was responsible mostly for fundraising. Let me tell you that fundraising for survival, before product-market fit, SUCKS. I did it for years and although we were successful in surviving I was tired of selling a vision before a product was built and realized I wanted to shift to bringing the vision to life. I let my co-founder know I wasn’t happy in that role so we swapped (he was ready for a change as well) and our business is thriving now because we’re both in positions that bring us genuine joy. He loves working the deals (investment/sales) and more technical components of the business while I love marketing our brand, executing on our customer promise, and building the team. At least once a week we both catch ourselves saying “this is so fun” about the work we do in our business.

2) Daily gratitude and excitement. I start every day by writing down three things I’m grateful for and three things I’m excited about for that day. This helps me start each day with a mindset of the positive things which especially is important when I’m dealing with the numerous challenges and inevitable negative events in life that happen.

3) I added manifestations outside of my business. At one point, I realized all my manifestations evolved around business success. Although my business is a big part of my life, there are things that I want to accomplish in life beyond my business. For some of my manifestations, the success of my business is a stepping stone, but for others like empowering women around the world or producing music, I could be doing those simultaneously for my time dedicated to passion projects.

4) Passion projects. I found myself rather depressed last summer as we recently moved to a new town and then experienced a big loss in my family. I decided to try something very new and scary: I enrolled in singing lessons. After my first lesson, I had so much fun and that was ultimately a turning point in growing out of my depression. I realize I find joy in learning new things so sometimes it’s figuring out how to map my backyard electrical system with our pool, converting my office closet to a music studio, or learning how to be a DJ and blend music or even produce my own music. Leading a women’s movement in my industry is another big passion project of mine that brings me joy and excitement. I prioritize this time, especially my weekly singing lessons, even around my work schedule when possible because of the value it brings to my life.

5) Awareness of self. Self-awareness has been a big topic for me, especially in the last year. A lot of my own growth has come from becoming aware of the way I show up to others, accepting my emotions as they come and letting them run their course, and growing to discover my authentic self (very difficult because it’s letting go of what others think). As I grow in this journey, I find myself happier, more content, grateful, and more present in life.

6) Prioritizing my partner and relationships. Every week I write down what I would like to do to make it a great week through my business, friendships, family, and marriage. Before, the only category that existed was my business and I’m sad to say that it came to a point where even my own wife no longer felt seen by me and overshadowed by my business. Unfortunately, stories of broken marriages are too common in the entrepreneur world but I realized that prioritizing my business over everything meant I would eventually lose my marriage. My business is still a big part of my life, but my connection with my wife is the most important and I am proud to say the experience has brought us closer than ever before. Also, the weekly habit also helps me stay well connected with family and friends too.

One of the best things about being a founder is that you can create your own definition of success and happiness. You don’t have to fit into someone else’s mold. You can be creative and passionate about your work while also having a strong focus on your relationships and health. This creates a well-rounded life that leads to happiness. One of my favorite books is Tuesdays with Morrie where the author states, “Do the kinds of things that come from the heart. When you do, you won’t be dissatisfied, you won’t be envious, you won’t be longing for somebody else’s things. On the contrary, you’ll be overwhelmed with what comes back.” This is so true, and it has taken me a long time to learn this. When I am connected with my wife, co-founders, family, and friends from the heart, I am truly happy. In fact, I have found that when I am focused on others and not myself, my happiness grows exponentially.

I recently spoke at the University of Texas Kendra Scott Institute for Women Entrepreneurs about the topic of leading in male-dominated industries. Since this event was exclusive to students/alumni/staff at the university, I decided I want to share some of my talking points with those who were unable to attend.

Develop Your Pitch To Impress

Now, believe it or not despite my accomplishments as seen to the rest of the world I have been plagued and struggled with imposter syndrome my whole life. Not only that but I was raised by parents who stressed the importance of being humble about accomplishments — let people know and respect you for what’s in front of them. I used to not let people know that I graduated from West Point or led over 80 Soldiers in a combat zone. “I want them to respect me for me before they learn about my accomplishments” is what I used to think. However, in a world where men can be quick to underestimate or bring on unconscious bias to women in their industry, it is essential to develop an introduction for yourself that breaks down those assumptions upfront. I personally have a long and short version depending on the situation or person I am speaking with and I now coach other women on improving their self-pitches. In our society, most women are not comfortable talking about themselves, let alone their accomplishments. I used to not be able to even write about myself and even hired someone to craft a bio about me. I couldn’t even put pen to paper about these FACTS about myself. However, I realized how important this is, especially in the industry I work in so I had to evolve to overcome this humility to communicate that I’m a badass in a minute or less(with the encouragement of my wonderful male co-founders!). I am proud to say I’ve progressed to FINALLY owning my accomplishments and last month wrote the following below about myself in only five minutes.

“Over the past 20 years, Marissa Limsiaco has broken barriers as part of a small percentage of women who graduated from West Point, led soldiers in combat, and today leads a company revolutionizing the commercial real estate industry. She is the recipient of West Point’s prestigious Army Athletic Association Trophy, a decorated combat Veteran, and named one of the most influential women in commercial real estate. In an environment where only 2.2% of venture capital goes to women, Marissa has raised millions for her company.”

The last thing I will add on this topic is that the pivotal moment for me to be able to own my accomplishments is actually believing it myself. We don’t realize how many negative voices we have that play in our heads at times. It takes time and deliberate effort but eventually you can re-record those voices and rewire your mindset completely.

Be Yourself

As I look at the leaders I respected most two traits are ones they all share: 1) they are authentic and 2) self-aware. At West Point, the women who tried to emulate a more masculine approach from their male peers were not respected as much as those that were just themselves. I observed some of these women were like two completely different people between leader and peer roles. I always saw this style backfire and will happen whenever you try to emulate someone else’s style that is not your own — man or woman. The best leaders are those who are most self-aware and genuinely know themselves. Your subordinates know when you are imitating or presenting your authentic self — they smell insecurity from miles away, and when they do, it’s more difficult to intrinsically inspire them to follow you. At the end of the day, leadership is figuring out how to motivate people to do stuff in YOUR own way.

Don’t Complain

I learned this lesson early on when I was at West Point. The Academy evaluated us on academics, military, and physical grades. The military grade was based on our performance in our company ranks during the school year as well as our summer training. Our second summer was spent in field training and there are only limited A’s that are awarded within each platoon. That summer I received the A and was a bit surprised because I did not perform the best at tasks such as land navigation, shooting, etc compared to my peers. When I asked my squad leader why I received the A he said that even though I wasn’t the best at all tasks, I never complained and always just executed whatever task was ordered despite being in really crappy situations as opposed to my peers (mostly men) who always had to gripe about something. It highly impacts morale and my optimism and motivation stood out to him. “The best followers can become the best leaders and I see that in you,” he explained. So ladies, keep that in mind. You stick out in a group of men when you aren’t the one complaining all the time. It can go a long way for you.

Find Your Woman Tribe

I never realized how important a woman tribe is until the last few years. When I look back at my West Point and military years, having women around me and women to look up to make all the difference. The saying is true, “When you see it, you can be it.” I was lucky to have my woman tribe from peers to mentors who wanted me to succeed. However, when I left the military and entered the entrepreneur world it was a huge struggle for me because I didn’t see any other women who walked in my shoes. I knew there were few out there but I didn’t know or have any connections to any of them. This led me to through some crippling imposter syndrome and my confidence was at an all-time low. It was almost as if I canceled or forgot about my own previous accomplishments — a woman who dominated in a world of men and led Soldiers in combat and graduated from West Point. I will go way deeper into this experience in another blog post, but long story short I finally found my woman tribe in the last two years. I’ll tell you that finding these women has been a game-changer for me, especially in the last year. They have helped me find my confidence and it feels stronger than ever before…we feel like we can conquer the world together. A win for one of us is a win for all — they are family to me now. So if you don’t have one, go out there and be deliberate about finding your tribe even if it only takes one woman at a time.

I love winning. If you know about my background (Junior tennis champion, West Point grad, decorated combat Army veteran, successful entrepreneur), you would rightly assume that I’m competitive AF. However, when the task of entering a pitch competition was presented to me six years ago in New York City I found myself way out of my comfort zone. To be honest, I wasn’t in it to win, I was only in it to survive.

So why would you enter your startup in a pitch competition? Win or lose — pitch competitions are a great way to get exposure for your startup and gather feedback from others. Even if you are not selected to advance, the exposure is worth it. You will learn a lot from pitching your idea or company and be able to improve for future pitches! Not only that but if you win, you sometimes get an awesome prize which can really help take your startup forward. Over the years, I’ve overcome the fear of pitch competitions and now have a garage collection of life-size checks with five victories under my belt so I thought I’d share my process with other founders.

Step 1: Determine the audience and requirements. This is a big one to know upfront because that will determine how you structure your pitch. For an investor crowd, you want to explain the go-to-market strategy and financial projections while a crowd full of customers care about how your product helps them. Also, how long do you have? I’ve participated in ones anywhere between 2.5 minutes — 10 minutes. This makes a BIG difference and I’ll tell you the shorter ones are so much harder.

Step 2: Develop outline and script. The shorter the time requirement, the more I stick to a script rather than an outline because every word matters. Developing the script helps to reduce the number of words in my head and gives me direction. It also ensures that I hit all the important points. One of the biggest factors for my success is my ability to craft my pitch into a story. The outline I typically go by for investors is: 1) attention-grabbing intro 2) problem 3) solution 4) how it works 5) competition 7)go-to-market/scale strategy 8) financial projections 9) team 10) Big close. For overall product pitches I don’t include financial projections and it’s tailored to the audience’s perspective of the problem and how we are solving it for them.

Step 3: Create slides. This is where I take my script/outline and translate it into pictures/graphs to slides for the presentation. The fewer words the BETTER — people are visual and you don’t want them reading slides when they should be listening to you. We use Slidebean for design (which is so worth it and way cheaper than hiring a designer). If animations are allowed I always include them by timing images appearing with my script. I’ll get into why in the next steps. Get Backed is a book of successful slide decks and a great resource to give you an idea of how other entrepreneurs pitched their ideas.

Step #4: Finalize timing and execution. This is where your presentation skills come into play. A mentor recently told me that pitch competitions are a lot like standup comedy — timing is EVERYTHING. I personally feel like an actor at this point ensuring my script/talking points and slide animations are in sync. One of the ways I finalize all of this is doing a video of myself doing various versions of executing the pitch until I find the one that sticks. I always want to make sure I come across as confident and genuine in my presentation style.

Step #5: Rehearse, rehearse, rehearse. Here is the most important part — rehearsing the finalized pitch over and over again. I usually give myself at least a week to practice over and over. I recite it while I’m driving, cleaning, walking my dog. My wife can pretty much present for me by the end of the week. I want my lines to be second nature where I can do it in my sleep. Why? Because I inevitably mess up or get distracted EVERY time I go on stage and the practice helps me bounce back in a way that nobody even notices (but maybe my business partner who practices a good amount with me as well).

Step #6: Visualization. 30 minutes to one hour before I go on stage I lock myself in a bathroom stall, close my eyes, and visualize myself going through my pitch. I learned this technique from my sports psychologist coach in college when I played Division I tennis. Visualizing makes me feel like I’ve already successfully done it once and by the time I get on stage it’s like the second time and makes me feel a little more relaxed.

Step #7: BREATH and have fun! Right before I step on stage I do some breathing exercises to calm my nervous system and remind myself that the jitters are excitement, NOT fear. Confidence and authenticity are mandatory. I tell myself I’m a badass and I’m about to make a valuable connection between my company and the audience. I let go and step on — I inevitably mess up or get distracted, but I always recover and finish strong.

Questions may be part of the competition after the presentation. Preparing for these is important not only for the competition but also for pitching in real life to investors. My co-founders and I always challenge our ideas more than anyone so I simply take those challenges and craft responses to them. I think of a question that may be asked and write down my answer. This way, if the question is posed to me, I’m ready with an intelligent response instead of pausing or rambling about something else.

Your co-founders can make or break your company. Over the years I made some mistakes in choosing co-founders and it ended up costing me a lot of money and in one case the failure of the business itself. In this article, I will share the qualities of successful co-founders from my own experiences and how they can help you build your startup into something great!

I have built four companies and worked with seven different people as co-founders. They say finding the right co-founder is like dating and this is absolutely true. The relationship you have with your co-founder ultimately ends up being very similar to a marriage. Things kickoff and always starts out exciting — people coming together with an idea that can make them a lot of money. I mean who wouldn’t be excited about that? However, every business has its road bumps and inevitably the strength of your co-founder relationship will be tested. Similar to marriage divorce rates, co-founder divorce rates are as high as 50%. It’s sad to see businesses with a lot of potential or traction fail because of the co-founder relationship not working out.

One of my current co-founders, Josh Feinberg, and I have known each other since high school (over 20 years now) and been business partners for six years. Despite being close friends, the dynamics of a co-founder partnership are different — there is a lot at stake and big decisions need to be made together. The balance of control, roles, and execution were some challenges we had to overcome together. We brought in a third co-founder, Frank Rogers, two years ago after Josh and I started our second company together, Otso. Frank’s presence brought a new dynamic forcing us to balance the established momentum between Josh and me with the new energy Frank brings to our team. The following are qualities that are essential to our successful working relationship together.

Skill Sets

The first quality that I look for in a co-founder is someone who complements my skill set. They need to know what you don’t know because the only way you will ever succeed as co-founders is if you bring different skills and knowledge sets to the table. I made this mistake in my first company when I partnered with someone who had almost an identical skill set and experience to mine. This was both our first business and there was just too much we didn’t know that we didn’t know.

Josh, Frank, and I bring very diverse skillsets to the table — Josh and I are both visionary people, but he is the industry expert with a mind that works a million times a minute and can craft solutions on the whim. He also is an expert negotiator who loves the art of a deal (and is damn good at it). On the contrary, I’d prefer to just execute within the business itself (especially sales/marketing), build the team, and grow relationships for us. I know I have a very strong presence on large stages/rooms and I love making connections and networking. Frank has experience in running and selling multiple companies so he contributes his expertise in finance, technology, and business processes. Frank filled in a critical gap between Josh and me being the one to slow us down when needed and the strongest at attention to detail. At the end of the day, what’s important is that each one of us is not only working on the things we are good at but also things we love and have fun doing.

Values

Another quality that co-founder relationships should possess is having shared values. Do you have the same outlook on what integrity means and how other people want to be treated? There are people out there who have a different definition of integrity. I’ve dealt with co-founders who heavily inflated the value they would contribute upfront, but brought little to nothing in actually executing what they said they would. I experienced another co-founder who straight-up lied about making an inappropriate comment he made despite multiple people who attested to hearing him. We now have a heavy vetting process around the ‘bullshit’ card for anyone we bring to our team. Did they really accomplish what they said they would or know the people they claim to know? If there’s one thing I’ve learned about life, especially through starting multiple companies, it’s how to sniff out bullshit from miles away. This is an extremely important skill to have!

Josh, Frank, and I have these shared values of integrity and bias to action: that we must always do what we say we’re going to do — no matter how big or small — so our partners never feel like they can’t trust us with anything important! We also share the value of selflessness — no matter the decision we take into account what is best for the company, our customers, or investors — sometimes albeit to a fault that others may disagree with. Ultimately, the biggest question we ask ourselves in regards to any decisions around values is “will I lose any sleep over this?” If this answer is yes, then we don’t do it.

Egos

We do not have any tolerance for egos or assholes, period. Of course, we all know every person has an ego that they battle, but what I am referring to is more about someone being self-centered, prioritizing themselves over the wellness of the team, or someone who refuses to admit or accept responsibility when they are wrong. One of the questions I ask myself about people I work with is “how would this person show up in a disagreement” or “how would this person react when they are confronted with constructive criticism?” Recently, I was meeting with a person who was interested to do work with my team. He showed a lot of passion and had a lot of experience to potentially provide value. However, I realized I stopped myself from making a critical suggestion to one of his ideas — his vibe was a bit too intense for me personally. Now, everybody is different and others may feel more comfortable around this person, but I knew that for MY team this dynamic wouldn’t work out. Openness and collaboration are key to creating the best ideas and you don’t want an environment where anybody is holding back ideas or criticism because of one person’s ego.

My co-founders and I have come up with some incredible out-of-the-box ideas because each of us feels seen by the others and trust there is no judgment or mockery no matter how crazy an idea may be. We each have accomplished our own professional successes through life but in no way does any of us leverage these as a pawn in disagreements or shiny objects to inflate our role on the team. Sometimes the best ideas are born when you feel comfortable exposing yourself, your fears, and your shortcomings to others who will accept them and help you grow out of them.

Vulnerability and Compassion

Vulnerability is not a comfortable place for many people, but it is integral to trust and respect in any relationship important to you. Let’s be real — the life of a startup founder is extremely high stakes and stressful. If one of us doesn’t feel comfortable raising his/her hand when he/she is struggling then it will grow into a bigger problem. We are all humans — we need breaks, personal relationship issues happen, family members, get sick, and the inevitable list of life challenges goes on. We are all going to be on our deathbeds one day and we know that how big we grew our business or how much money we make for ourselves won’t matter as much at that moment as the relationships we have with the people we love. Our compassion for each other as fellow humans is extremely important to our success as a team.

The co-founders I have around me today are not thinking “What can Marissa do for me?” Instead, they are each thinking “How can I help Marissa become a better person today?” We are truly committed to being the best versions of ourselves for our customers, partners, and each other. That’s what allows us to be vulnerable around each other. That’s how we get the best ideas. That’s how we win.

In this blog post, you will learn about three mistakes I made in my 20-year leadership career and how they’ve influenced my approach today. I’m a West Point graduate, Army combat veteran, and 4X entrepreneur. I’ve led teams of all sizes from winning championships as an NCAA Division I athlete, deploying and leading 100+ Soldiers in Iraq, and leading teams for the multiple companies I’ve created.

Leadership to me consists of three simple principles: Effectively communicate your vision and expectations, lead by example, and just simply care for people. I grew into embracing these principles as my own through various experiences on my journey, good and bad. This post is not just about the lessons I’ve learned; it’s also to share that nobody is perfect and some of the most important lessons unexpectedly come from mistakes that you will inevitably make.

Lesson #1: Communicate Consistently and Transparently

The people you are leading need to know where the team is headed and what is required to get there. As a leader, it is your job to get them to buy in with full dedication to accomplish the vision and it’s important you ensure they understand how they contribute in their role. Feedback loops are also important — in the military, we did monthly, quarterly, and annual reviews for every Soldier and I continue this with teams I lead today.

One of the mistakes I made as a young lieutenant was signing off on a poor annual review of someone on our team who was never formally counseled on her poor performance. She was not a direct report to me, but I was part of her leadership team so my signature was included even though I did not write the review. She was taken off guard and had no idea she was performing poorly because her direct supervisor did not give her any of this feedback. Perhaps the 23-year-old in me was intimidated since she was so much older and had significantly more experience in the Army so I just avoided her and left it to her direct supervisor. As a result, the bad review led her to retire and there was always a part of me that wondered if she would have turned it around if we would’ve formerly counseled her prior to completing her review.

Lesson learned? Looking back I wish I would have at least ensured there was proper documentation and that she was formally informed of her poor performance. Today, I take every step to be transparent with poor performers, and sometimes those conversations are hard, but they are absolutely necessary. Lack of trust and resentment starts to grow when this type of necessary feedback is missed. A lot of people will sometimes delay these conversations or avoid them completely because they don’t like feeling confrontational or are worried about what people will think of them. The reality is that leadership isn’t a popularity contest and I will tell you the longer you wait to confront the behavior the bigger the negative impacts it will have on your team.

Lesson #2: They Are Always Watching You

As a leader, your presence matters and your team is always paying attention to your actions. How would it make you feel if you were instructed by your boss that every single person on the team has to show up to an event by 9 AM, but the boss doesn’t stroll in until 10 AM and obviously just woke up? It sucks huh? There’s that resentment and negativity that could sneak in again.

My ah-ha moment with this lesson was when I was a 19-year-old at West Point. I played the number one line for our tennis team, but I was only a sophomore. We had a captain who was a senior so my mindset was that I just needed to play and my worries were only my own. I was still struggling (like everybody else) adjusting to life at West Point and found myself late to practice a few times. I was late to an early morning practice again where I found my team captain, Annie, and my coach were waiting for me — both arms crossed. Annie told me “You are only a sophomore but everyone looks up to you since you are the top player on this team. You need to step it up and can’t be late because they are paying attention. I need your help with this.” Now, we all looked up to Annie immensely so these words coming directly out of her mouth (instead of my coach’s)carried a lot of weight on me. From that moment on, I knew I had to get my shit together and grow up a bit to support her. Fast forward to my senior year, I found myself having similar conversations with younger classmen — the torch had been passed!

Lesson learned? Never underestimate how much people look to you as a leader — you must emulate the example of what they should follow. They need to feel like you are with them every step of the way and not just there to carry power, protect your ego, and bark orders. At the end of the day, leadership is service to others.

Lesson #3: Boundaries Are Important

The relationships you develop with your team may become some of the strongest bonds you will have in life. There is something truly special when several individuals grow in trust and respect to become one kick-ass cohesive unit. Some activities for team bonding may pass on to some personal aspects of life - like you begin to know and perhaps even become friends with them and their families. Dining together or participating in fun activities outside of the work environment may serve as great ways to strengthen the bond of your team. However, be mindful of how crossing into more personal relationships may impact your professional one.

Five years ago I was growing another company and we were in startup mode. We’d recruited some teammates from outside the state (one moved to Texas from another country) so to save some money for the company, I ended up hosting them at my house. What was originally thought to be a temporary arrangement (maybe a few weeks) became a year-long roommate situation — one of them flew in once a month and lived with my wife and me for a week or so at a time. At first, it was super fun — I truly enjoyed and respected these people and we had a lot of things in common. However, the boundary between work and personal started to disappear, which started to even take a toll on my marriage. Ultimately, the professional relationship came to an end in a very awkward way. It’s quite uncomfortable to tell someone you no longer want to work with them when they are scheduled to live with you for a few more days.

Lesson learned? Needless to say, my wife and I will not be opening our home to any more roommate situations with coworkers. My cofounder did this as well and we are all in full agreement with this policy. I’m lucky that despite the awkwardness we still maintained good relations with those coworkers that stayed with us — we wouldn’t hesitate to hang out again if we were in the same city. You have to be mindful and ask yourself — “in the case that shit goes wrong in any part of my relationship with this person that works for me, am I going to prioritize the friendship or professional relationship?” You will ultimately have to choose one.

Becoming a good leader is a work in progress and doesn’t happen overnight. As with anything else, there are always going to be mistakes made and it’s important for leaders to learn from them in order to grow. Your team is always watching so you want to make sure they know where the lines are drawn between what’s acceptable behavior versus unacceptable behavior at work. It’s important to understand that you can always learn and getting better at anything requires time, effort, and humility.

The first thing I think of when it comes to entrepreneurs and mental health is the phrase “all in.” This concept, that successful entrepreneurs are always going all-in, has become a cliché. Sure, some people who struggle with mental health issues have managed to create thriving businesses. But for many others, this idea has been destructive. In our culture we idolize success at any cost — but what does this really look like? What’s it really like to be an entrepreneur?

There can be a lot of glamour and spotlight but what people don’t realize is the stress, pressure, doubt, depression, and anxiety that can overcome an entrepreneur’s life and impact their personal/professional relationships if they don’t have the proper support systems in place. Entrepreneurs have to present themselves as confident and there is an identity that we have to uphold, whether it be through our business or personal lives. There is a fear of failure that can keep us from asking for help and admitting when something feels wrong because of the shame factor.

Some of the most common mental health struggles that entrepreneurs face are:

- Stress, anxiety or depression.

- Difficulty managing their time.

- Unclear financial situation due to expenses and lack of income streams.

Stress is a huge issue for people who start new businesses because they have so much going on at once — even if it’s your dream job! It becomes even more difficult if these struggles go on for a long period of time — starting and growing a business is a marathon and can take many years to find the market fit and grow successfully.

I’ve been an entrepreneur for the better part of the last decade. At one point, I had many nights of lost sleep and put personal relationships, especially my marriage, at severe risk because of the financial concerns around our business. However, I am lucky to have an amazing support network, supportive cofounders, and an inspiring wife to help me through those tough times.

Here are some tips I like to share with other founders about maintaining mental health throughout the entrepreneur journey:

Tip #1: Don’t be afraid to take some time off from your business while you address what’s going on or practice self-care and take a break. This has been a big struggle for me, but at the end of the day, it is more important than anything else that we are kinder with ourselves — after all this is just one chapter in our long lives! Be mindful of when you prioritize work over spending time with family/friends or spending time being present during quality moments. Ask yourself “Do I have to finish this now? What if I can give myself another hour?”

Tip #2: Develop a strong support network of people who are invested in you and know the realities of entrepreneurship.

Tip #3 Meditation, yoga, and exercise. It’s so important to be mindful of your own energy and tension your body picks up from all of the stress. Give all of that unwanted stress-energy an outlet! For meditation, Insight Timer and Calm apps are what my cofounders and I use!

Tip #4 The Panda Planner is my secret weapon against overwhelm. It’s a planner with an innovative system that allows me to focus only on the most important tasks during any given day, while also reminding me of things I’m grateful for and excited about. I use it every single day.

Tip #5 Journaling is a great way for me to get my feelings out without having to talk through them or take time and energy analyzing everything. Sometimes just sitting down quietly when I am feeling overwhelmed helps tremendously.

Tip #6: Therapy can help you work through your problems and it is great to have someone outside of the situation that understands how difficult dealing with mental health issues may be. I’ve been routinely seeing a therapist for the last eight years and the conclusion I have come to is that EVERYONE should find a therapist that is right for them — even when things are going really well in life it’s great to have a third-party that you trust to process with.

Tip #7: Medication for an anti-depressant, anti-anxiety, or whatever your doctor deems appropriate may be a good idea if you find that there is no other way to cope with the issues. Our society can have a negative stigma towards medication (mental health in general) and it’s not for everyone but these have helped me personally for a number of years.

Tip #8: Get your sleep, too! It’s difficult sometimes but try and routinely get at least eight hours of sleep each night. I like to listen to a book, podcast, or meditation right when I lie down in bed to shift my mindset from any work thoughts to prepare for relaxation.

Tip #9: Have a passion or creativity outlet outside of work. Mine? I play music! I love to play the guitar when I have some free time. It’s a great way to relieve stress after work and it gives me an opportunity to lose myself in something that is creative.

Tip #10: Create relationships with other founders with who you can openly discuss these struggles. Founders have a unique experience and finding others that understand what you are going through is so important.

Tip #11: Affirmations are an extremely powerful tool that can make all the difference in your life. I’ve been doing this practice since college. There are many ways to incorporate them into your routine, either by doing one each day or making a list and reading it every morning before you start on whatever task awaits you.

Mental health issues are common among founders but not widely discussed and should not be ignored. You must prioritize your mental well-being if you want to sustain your business over time. It’s important to take care of your physical and emotional well-being as a founder so you have energy for all aspects of running your company.

In February 2020, we sold our house and were excited to buy a new one in Austin. One month later everything changed with the COVID crisis. As we adapted to the ‘new normal’ of physical isolation from friends, family, and everything we loved so dearly about Austin (music, town lake, the Greenbelt, etc.) my wife and I found ourselves feeling isolated miserable- trapped between two worlds without any way out but up. When you’re stuck in a state of unhappiness there are two things you can do 1) do nothing and remain unhappy or 2) change something and fight for happiness! We chose option 2 that came in the form of a 32' foot RV, which we named Pierre Ace Chateau, that allowed us to travel around the country visiting places we never thought we’d find ourselves in.

Our time living in an RV was a transformative experience for my wife and me. By the end of our RV journey, we were closer to each other than ever before and had grown immensely personally as well as professionally. I cannot speak for my wife because she experienced her own personal revelations on our adventure but can say that we grew together while exploring different parts of America one state at a time.

A lot of people ask me how I managed to fundraise, sell, and grow my company from miles away with no office or phone line connection? Here are some key components to RV living that allowed us to work full-time.

Data Plans: My wife’s therapy practice turned virtual and I work remotely so we always needed internet connection. In fact, we needed a good connection because she was using video for every session. We upgraded our Verizon phone plans to add hotspots plus purchased an additional line for another hot spot in case we ran out of data on one device. We also purchased a hotspot from another carrier in case there were areas where Verizon was weaker (this only happened two or three times out of hundreds that were used during the year though!

Cell Phone Booster: We also had a cell phone booster that would help in areas when there was little to no signal. It gives you an extra bar so this came in handy when we had no signal and gave us enough for text messages or making calls.

WiFi Extender: This ultimately helped set up our own internal network which meant we didn’t need repeated wifi connections whenever we parked at a park or someone’s house. This also helped grab wifi from someone’s house to the street or if the router was far away at a park.

Dedicated Workspaces: This was important because as mentioned my wife is a therapist, and needed her own space where other people couldn’t hear her conversations. We ended up with our Class C Motorhome because it had the division between the bedroom and the rest of the living space- it came equipped with an actual door that could fully close giving us both privacy during phone calls. I set up in the kitchen area while she transformed our bedroom into her office. We also noise-canceling headphones as well as sound machines for each person so we couldn’t hear each other.

Balancing Travel Time and Work: As mentioned, we were in a new location every one to two weeks. Since we are both self-employed, we were able to set our own schedules. We usually dedicated Fridays for traveling so we could use the whole weekend to explore the newest place! I would catch up with my work by doing later hours during the week as well as Sunday evenings. This routine actually made me more productive- COVID meant less time spent out at restaurants etc — so anytime outside of exploring I was able to work.

The Power of Environment: On our adventures, there were a number of moments that I noticed the power in surrounding environments. Some places had more energy and others provided solace and peace; each with its own unique vibe. For example, at Zion National Park we would drive through miles upon miles of mountainsides while Florida’s beaches was always so refreshing and an escape from stress. Some places gave me more creative inspiration while others provided peace of mind when I needed it most.

If you’re looking for a way to live more simply and spend less time in the rat race, an RV is worth checking out. We had no idea what we were getting ourselves into when we decided to try living on our own terms for 10 months. What did happen was that after one year of travel through North America, exploring new places while working remotely with my company from wherever there’s wi-fi or cell service, I came back refreshed and ready to take on life again — this time without leaving my home base. I always tell people you never know until you try it, but it may be possible that RVing could just change your life too!

I was a freshman cadet at West Point when 9/11 hit and following graduation I deployed to a combat zone in Iraq for 15 months in charge of over 100 Soldiers. I’ve found myself in multiple undesirable situations where I had to make quick tough decisions that impacted actual lives. A lot of those experiences not only shaped me as the leader I am today, but also prepared me for situations like the COVID-19 crisis.

My company, Otso, launched last month. Great timing, right? We launched our company and then the entire world felt like it stopped. Just like every other industry, the COVID-19 crisis has put a pause or killed multiple startup businesses around the world. There are founders struggling to find funding or have lost customers, revenue, or in some cases any path to success with their business model.

For me, the most important factor in successfully leading through a crisis is your own mindset. Here are some tips for founders, especially CEOs, on how to foster the mindset required to effectively lead in our current crisis.

#1 Accept The New Reality.

When a crisis hits, it’s normal to go through emotions similar to the stages of grief. We start with the denial which turns to anger and then depression. As important as it is to process these emotions one needs to eventually get to the acceptance stage and move forward. In the military, we were trained to pretty much skip those initial stages and get to the acceptance to survive and lead. After all, without quick decisive actions, more lives could be lost in those situations — there simply is no room for error or hesitation.

I believe exemplary leaders in crisis are the ones that get out of denial and arrive at acceptance faster than others. Panicking or doing nothing would do no benefit to my teammates, investors, or customers. I gave myself a whole Saturday to be angry and depressed for my company, but that was it. I woke up the next day and put it all behind me to accept and better understand the new reality of our situation.

#2 Kill The Fear

Fear can cause panic, paralysis, and may prevent execution. It is important to recognize when fear starts to take over your thoughts. As founders, we are always running various situations through our heads and have to plan for worst-case scenarios. However, when a crisis happens our minds maybe even more consumed with increased thoughts of threats to the success of our company. Having an increased amount of uncertainty and loss of control can cause a big downward spiral. There’s a difference between awareness and obsessiveness. Operating off of constant fear may negatively impact the decisions you make for your company. Ask yourself, “Am I thinking of thoughts that can be proven to be true today?” or “Does this serve me right now?” If your mindset is in constant fear you may make the wrong decisions. Fear does not serve you well and is a waste of energy. Most importantly, you do not want to pass that vibe to your teammates or people that look up to you.

#3 Overcome Set Backs

Nobody likes taking steps backward after making progress. In 2006, I deployed to Iraq thinking I’d be there for 12 months. Once our boots hit the ground, we were already counting the days until our return home. Everybody gets two weeks off called “mid-tour” leave where they can go home or travel. I purposely scheduled my two-weeks off towards the end of the deployment knowing we’d be packing when I returned. While I was on my leave President Bush got on the television to tell everyone that deployments would be extended to 15 months. So, instead of coming back from my leave with three months left, I had SIX months — that’s half a year! I was depressed thinking I would spend two birthdays and two of each holiday away from home. This was an extremely difficult mental hurdle to overcome, but we had a duty to serve so we reset our mindset and re-evaluated plans to accommodate our deployment extension.

It’s certainly not life or death in the business world, but survival mode may mean you need to take a few steps back from progress as well. Some founders may have to re-evaluate product-market fit while others need to find an alternate revenue channel to survive. You may need to cut variable costs or certain roles on your team — these are hard decisions but necessary to survive in a world of more uncertainty. For some founders, the crisis may have made your product less relevant in the current market so you may need to go back to a super lean budget until you can figure out your next step. Plan for the worst — double or triple the numbers of whatever you ‘think’ maybe the timeline or budget to recover. Taking steps backward is extremely difficult for anyone, but in cases like these, it can be necessary to stay alive as a business.

#4 Open Up To New Possibilities

Once you can shift your mindset to embrace the crisis, some new opportunities or creation may appear. Priorities may most likely change for you in these scenarios as well. I was in Iraq during the Surge of 2007 which made my fueling and arming operation extremely important. Before the surge, nobody cared how fast our system could fuel a helicopter. However, in anticipation of the increased business that was about to arrive, we saw an opportunity to re-configure our system to make it faster. This re-configuration did not follow the training manuals the Army set for the system, but we were able to convince our leadership to think outside the box and allow us to design a more creative solution. Long story short, leadership started caring about how fast we can fuel because we went from servicing 20 helicopters on a busy day to 100+ a day during the Surge. Since we re-configured the system we increased our service speed by over 900% — my team won awards for running the fastest operation in Iraq at the time.

In relation to the current crisis, we had to shift priorities a bit as well. All of our sales content was developed, but when the quarantine began we tossed that out and had to develop entirely new content. Also, since there currently aren’t a lot of commercial real estate deals happening we re-focused priority on increasing production of helpful and relevant content via blogs, email campaigns, etc. Also, our target customers are out of the office so we are currently targeting and testing with other segments.

#5 Stay Engaged

The frequency and speed of communication are even more essential during a crisis. The environment is constantly changing along with your decisions. In the military, we already had set routines for status updates and meetings, but when a crisis happened there was a set amount of hours you had to report a situation from the time it happened and leadership engagement increased with requiring more status updates in a day. As a leader, it was extremely important to gauge the morale of your Soldiers and keep them informed and motivated. Everybody handles stress differently so overall engagement with teammates is vital to ensuring everyone remains safe and continues to execute.

As founders, it is important to stay engaged with investors, teammates, and customers during this time. You will never have all the answers, especially with so much more uncertainty, but be transparent about how you plan to move forward. Identify the risks and set expectations that decisions and outcomes may rapidly change, but that you will remain engaged if anything does change. They want to know you have a plan, but also want to make sure you are realistic. There is a constant fear of layoffs so ensure you are engaged to either be reassuring if that is the case or upfront about how things may change in the next 30–60–90 days. During a crisis, remember that no news only makes people more nervous and scared.

With the right mindset, times like these can still offer a lot of opportunities for companies. For my team, we discovered Otso can play a pivotal role during COVID-19 as critical financial aid to businesses and landlords. They need us now more than ever. The last economic recession expanded the gig economy via Uber and Airbnb and downturns birthed companies like Trulia. Stay open and do what us founders do best: continue to create and problem solve. The market still has a lot of space for unicorns and new disruptions.