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My Hopes for the Recently Laid Off

I remember the first phone call that I got from a friend who was laid off last year.

“It didn’t make sense,” he said. The late-stage startup hired him less than two months before, and yet they didn’t have enough cash to justify keeping him or dozens of the other recent hires.

He was confused, hurt, and most of all scared.

Many of us seek jobs for the stability they provide, and when that’s ripped out from under us, we’re in fight or flight mode. Do you run away for a while? Take a break from reality? Or immediately start calling up everyone you know for a job?

I’ve been there – stuck in a situation that you didn’t want to be in with no idea what to do next.

It’s hard.

You may feel like crying, screaming, or just withdrawing for a while.

That’s okay. It’s okay to be emotional about work.

We spend much of our lives working and often wrap our identity around what we do. Having that taken from you without warning is like taking a bottle away from a baby for the first time. You’ve always known where your source of income (and for many of us, worth) is coming from. And now you don’t.

Layoffs Hit Close to Home

When I quit my stable job, I had a startup idea and venture funding promised by an investor. It didn’t feel risky; it felt like the next logical, safe move in my career.

Then, shortly after we started working together, the investor made a move on me. Not like a jab in a basketball game or even a dance move at a party; he expressed sexual interest in me.

I had to get out.

So I left the company… technically by choice but more because of the circumstance. And then I had nowhere to go. No idea what to do next. For a few days immediately after leaving, I felt like a vegetable in my own skin, barely surviving.

Then, reality set in.

Never in my working life had I gone without a paycheck. I needed to make money.

I didn’t want to go work for someone else. Believe me, if you’ve experienced the kind of behavior that I did, you need space to recover, and your confidence does too.

So I started exploring other ways beyond the traditional, career-oriented methods to make money.

How to Hustle a Side Hustle

The year before, I helped a friend edit her book on how to set up your house as an AirBnB. That sounded interesting and fun, I thought. Why not give it a shot? I love hosting friends; what better way to show your hospitality and make new friends than invite them to stay in your home?!

I had a blast coming up with the welcome letter and description too.

^my AirBnB welcome letter

Next, I started reorganizing my home. Weeks in, I finally made it to the furthest back closet – you know, the one we all have where we store all our junk that we hope no one finds.

That’s when I found a couple of old boxes of Pokémon cards. I seemed to remember my Dad trading them on eBay when we were kids, and with his permission, I listed a couple of them on eBay.

One of those cards made me (and my Dad) more money than I made in a full weekend of AirBnB!

I had always wanted to learn about OCR and saw this as the perfect opportunity. Painstakingly, I took pictures of each card and sorted them into bins. Then, I uploaded those photos onto my computer. With a few lines of python code, I was able to quickly read the description of each card and organize it into a Google Sheet for my Dad and me to share. He and I spent hours combing over cards, deciding what to buy or sell.

We continue to trade Pokémon cards to this day. Unfortunately, with my startup, I don’t often have as much time as I’d like to spend with him on this. I will always value and treasure our early Pokémon card trading days.

With the combination of AirBnB, Pokémon, and a handful of side-of-the-desk-consulting jobs, I supported myself. I certainly wasn’t making the kind of money I did before, but I slowed the bleeding.

Not only that, I discovered new, interesting hobbies that I can continue for the rest of my life while also becoming closer with friends and family. 

Make the Most of a Bad Situation

For all of you going through a layoff right now, there is hope. I hope that you will use this time to explore your passions.

Did you really love your job? If so, by all means, go after another version of it somewhere else.

If not, is there another way that you can make money doing more of what you love? Let yourself explore your interests outside of the traditional career mold. You may surprise yourself – use this gift of time to become closer with a loved one. Or perhaps begin to carve out a new career path.

I recently listened to a podcast by Mel Robbins where she interviewed Jamie Kern Lima. Jamie described the difficulties she encountered while starting her business. Many investors told her – straight up – that women wouldn’t buy makeup from someone who looked like her. She took beating after beating from people who said she was crazy, not smart enough, and not good enough. She worked odd jobs to support herself, never letting their words convince her to give up. Instead, she framed her experience as this:

“The seasons in life that are setbacks are actually setups for what we’re called to do.”

Jamie Kern Lima Tweet

I hope that you will use this time to set yourself up for what’s next. I’m convinced that incredible careers, companies, and life experiences will be born out of this difficult season. I can’t wait to see what you do.

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You Can Do More Than You Think: Practice

Historic Cullen Building at Southwestern University

The importance of practice | Don’t be afraid to try something new

My high school basketball team worked harder than any other team I’ve ever had.

We practiced year-round. In season, we practiced 6 days a week, even when we had games. Our strengths were our endurance, team comradery, and muscle memory. Truth be told, we ran more during our basketball practices than I ran in my track or cross country practices! And we did the same drills, over and over: quick feet, jab steps, punch passing, etc.

Not only did we work our butts off in the gym, we also set goals for each game. Think of it as the basketball version of OKRs (and this was well before OKRs gained popularity). We had targets for shooting percentages by 2 pointers and 3 pointers, turnovers, assists, offensive and defensive rebounds, and more.

If we exceeded our targets, our reward was that we almost always won the game. Our coach would also reduce the amount of running over the next week. If we failed our targets, not only did we typically lose, we also had to do sit-ups for each basis point that we missed our goal.

In one (rare) scenario where we lost and played particularly badly, we had to do 532 sit-ups. 5-3-2. These days, I’m happy to do 30 sit-ups, much less over 500! But we did every single one of them. As a team.

We knew that based on how we practiced and played, we can and should have done better. We held ourselves accountable. And you know what? We won the state championship later that year. We were the first women’s team from Martin’s Mill to win state ever, and the first for all genders since 1949.

I’m not the tallest or the fastest. I don’t have the best hand-eye coordination. But what basketball taught me was that if I did enough reps of anything, then I could get good enough to be better than average.

That’s how I learned the importance of practice.

It’s also how I learned to not be afraid to try something that I’m not naturally gifted at right off the bat.

Face Your Fears

Let me give you an example.

I was wrapping up my first year of college and needed to find a summer job. My closest friend found an on-campus events coordinator job, and I thought it would be fun to stay on campus that summer with her. The only other role available was a summer internship at the admissions office. The admissions intern mainly gave tours of the campus to prospective students 2-3 times a day.

Many of you who know me now may not believe this, but I was painfully shy at 19 years old. As one example, I was afraid to talk to strangers on the phone. I used to call my mom and beg her to make a call on my behalf.

I would literally panic on the phone with a stranger, palms sweating and heart racing. Just the idea of speaking to someone I didn’t know terrified me. Fortunately, my mom recognized the impending panic in my voice and agreed to make calls for me. That said, I was NOT ready to give tours to 50+ students a day.

Then, I remembered my basketball training. Giving tours can’t be that different than flexing and strengthening a muscle, right? So I applied for the job. To make sure I landed the position, I asked one of my professors to give me a recommendation. (This is how I first learned about the importance of referrals and reputation; more on this later.) Turns out, he was friends with the admissions hiring manager! Bingo. I landed the job… for which I had absolutely no skills.

Walk the Talk

I approached my tours how I approached every basketball game. I practiced, and I practiced, and I practiced. My parents ingratiated me with listening to every iteration. Many of my friends did too. Days before the internship started, I talked myself hoarse. Then, I started practicing in front of a mirror with memorized words and hand gestures.

I’ll never forget that first tour. My backwards-walking skills needed improvement, to say the least. I still laugh to myself thinking about the faces of prospective students and parents who tried to warn me before I banged the back of my head on a car window while crossing the parking lot backwards!

I had to use notecards because I nervously forgot my lines a few times. Still, I made it through. The second tour went smoother, as did the third and fourth.

After a couple of weeks of actively giving tours, I had it down. So much so that I started making up jokes. The parents loved it. I also told stories about our historic buildings.

For example, the Cullen Building staircase has unusually short steps. I would normally take them two at a time to classes. For purposes of the tour, however, I would slowly, painstakingly walk up each step, explaining to the group of prospective students and parents that when Southwestern opened for women, the female students weren’t allowed to show their ankles. They had to take tiny steps to avoid impropriety. 👀

“Can you imagine what those professors would have thought of me in this tank top!?” I’d joke, eyes open wide in mock horror. (It was over 100 degrees most days that summer!)

Historic Cullen Building at Southwestern University

All that to say, we had a stronger application pool that year than ever before… in no small part due to my tour and also, our amazing admission staff.

Practice, Practice, Practice

I share all of this to tell you – don’t be afraid to try something new that you don’t feel equipped for.

Want to learn to code? Practice every day for a month and see how amazing you become.

Want to learn a new language? There is no substitute for practicing daily with a friend.

Afraid of public speaking? Practice in front of a mirror and then groups of friends and family.

You may just find that you love learning new things. And what a gift that would be! 

You can do more than you think you can.

Practice, practice, practice.

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How to Land Your First Customer

Maybe some people are inherently gifted with the ability to sell anything. For my cofounder and me, sales was a learned skill. Truth be told, we’re still learning, and I expect that we will be learning and improving for the rest of our careers. We completely lucked into our first customer; my cofounder had been writing blogs about getting data out of Yardi for years, and a prospective customer came to him about providing data integration as a service (heck of a market demand, amiright?!). Landing our second customer was much harder. I’m sharing our experience in the hope that it will help you land your first customer.

There are a few key strategies that worked for us. First, we needed a fully-fledged product to sell. We also needed a good website (the modern-day storefront). Then, we had to sort out a good pricing strategy. Finally, we needed to find people who wanted to buy from us. I’ll walk through each of these steps for you.

Create a Product that People Want to Buy

This should go without saying: you need a product to sell that is 1) serving a real need and 2) at a price point that make customers willing to part with their hard-earned money. I am NOT in the camp of selling a product that you don’t have. In my opinion, this results in stress and confusion for your engineering teams that ultimately leads to poor performance, bad engagement, and ultimately high performers leaving your company.

We will often sell folks on new features or services that we’re currently building. However, unlike many salespeople (because again, we aren’t salespeople by trade), we’re incredibly transparent about our product stage. Plus, if you’re a startup, you need to be up front that you are early stage and looking for a partner to grow with you. Having a good reputation early is critical to your success, and transparency is key to trust. I guarantee that we lost prospects because of our transparency. However, we would have had a lot of churn if we were dishonest. And we don’t roll that way anyway.

Short story is that you need both supply and demand for your company’s product.

Design a Good Website

I absolutely love the book, “Don’t Make Me Think” by Steve Krug. If you’re designing your company website, buy this book. Now. And no, I don’t know the author and am not getting any kickbacks (currently…).

Websites are the modern-day storefronts. Instead of walking down the street to find a product, prospective customers google their questions or needs. If your website ranks high in their results and has an interesting sitemap, then they might just “walk in” and click your company’s link.

Copy outranks site design all day, any day. If your website doesn’t explain what you do well in the first three seconds, then you lost that prospective customer. They’ll go back to their jaunty walk down the proverbial street looking at all the fun, shiny objects.

At CREx, we were fortunate in that we had the skillsets to build websites with good copy in-house. If you don’t have that, then by all means, spend what you can to get good copy and a not-bad looking site.

Define Your Pricing

We screwed up on pricing several times before we got it right. To all of our prospective customers who were our guinea pigs, thank you for your patience. We now know what we are talking about and would love to hit the reset button.

In the real estate tech market, software companies price using all sorts of creative methods. Some of the most common include pricing per square foot, assets under management, per user, per property, and many, many more. We tried each of those methods, and each time, we had difficulty communicating to our customers “why”. Why didn’t we price by some other method? Would it be more expensive for them over time? (Or, often, pricing that way was too expensive today). Ultimately, we chose to price in a way that felt authentic to us. 

We figured that if the pricing model was easy for us to understand, then it would be easy for our customers. And you know what? I think we were right. At least, we grew 894% year over year! That ought to count for something.

Moral of the story is to not be shy about trying different pricing models early on. Troubleshoot until you figure out what makes the most sense to you and to your customers.

Find Customers

CREx has never paid for advertising. While we did get our early consulting customers through relationships, our initial SaaS customers came to us. I attribute 1,000% of our success to my cofounder’s content marketing strategy.

Vimal Vachhani wrote quality blog posts on topics that our prospective customers would google. Our website then ranks highly in search results (based on good SEO practices). Once a prospect goes to our website and reads the post, they will be prompted to download a free whitepaper for more information. Any new prospect’s email is automatically added to the CREx subscription list.

This resulted in CREx achieved nearly 1,000 email subscribers over the last year and a half. We now have several free whitepapers available on our CRExchange and CREx Software blogs. We also amped up our LinkedIn presence and created a community for real estate tech users on Slack called CREx Connect. Reach out if you’d like to join.

Sure, it’s more effort to create content regularly that’s good and interesting. It’s also more authentic, and that authenticity will win you more loyal customers. It’s loads better than throwing money like spaghetti at the paid ads wall and hoping something sticks.

Conclusion

It’s not easy to ask strangers and friends to give you money. Yet it’s much easier if you have a good product solving a real problem, a legitimate website, and a solid pricing strategy. Use content marketing to your advantage. If you follow these four recommendations, I guarantee that it will help you land your first customer.

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When You’re the Best, You Have a Target on Your Back

Right now, CREx Software is the underdog. We’re competing against an incumbent company-that-shall-not-be-named. Our competitor is better funded, has been around five years longer than us, and has name-brand recognition. While we actively pursue name-brand recognition, our goal is to fly under the radar for as long as we possibly can. Why, you ask? Because once we start becoming known as the best, our backs become etched with the painful, semi-permanent tattoo of a bright red target. When we become the best, we will have a target on our backs and have to work even harder to win.

Let me give you an example from my past.

Texas Academic State Championships

It was freshman year of high school. Like any proper nerd, I competed in academics. And not just any old academic competition: UIL, the big leagues for Texas public schools. Every class of school across the state vied for district, regional, and state championships. My high school was a legend in the Literary Criticism competition.

It all started when my high school English teacher, a former National Merit Scholar, returned to Martin’s Mill ISD to teach. She was the first Martin’s Mill student to win the state Literary Criticism (fondly called “Lit Crit”) competition. When she returned to teach English, she used her own methodical approach to theory and memorization to coach our Lit Crit team.

Making the team was a huge deal. Freshman didn’t often make the cut, and when I was selected to join the team as an alternate during my freshman year, I was ecstatic. We had an incredibly intelligent group. So intelligent, that we won the state competition not only for our small school sized group but across all schools in the entire state of Texas. This is from a tiny, East Texas public school with an average class size of 35 students! We beat the Westlakes and Pearlands and Highland Parks (all top public schools in the state). Insane.

The next year, we returned to the state competition with 3 out of the 4 same team members. Everyone already knew we were the team to beat, and yet, we made sure they were all reminded of it. We actually debated having T-shirts made with our motto, “It’s not hubris. We’re just that good.” And you know what happened? We got second. For the first time in years and years, the Martin’s Mill Lit Crit team didn’t win.

I had amazing coaches (both academic and in sports), good talent, and a hard-working spirit. Learn how I tuned out the second commenter, a Negative Nancy, here.

It's Easy to Revel in Success. It’s Harder to Maintain It.

What I learned from that experience is this: no matter how good you may think you are, there are so many other smart, innovative people out there trying to find a way to be better than you. Yes, we should all be intrinsically motivated and aim to beat our best. But that doesn’t work for everyone. For those people, you need to know that YOUR best will not always be THE best. Someone, someday, somewhere will come along and unseat you. It may happen after your career is long over, but it will happen. With that knowledge of the target on our backs, we must work harder every day, every minute.

It is hubris. No one is that good.

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On Getting to Choose Who You Work With

I chose to cofound CREx Software in part because I got to choose my cofounder and teammates. In many roles, you don’t get to choose who you work with. In startupland, that choice is always yours.

Each Job Is a Chance to Level Up the People Around You

I interviewed for a LOT of jobs over the years. One particularly memorable interview was with a fast-growing real estate tech firm. The interviewer said he’d been involved in so many interviews that he didn’t remember the role that I was interviewing for. And when I told him the job title, he asked me why they needed someone for that. 🤷🏻‍♀️ In retrospect, he probably knew what he was doing and used ignorance as an interview tactic. Smart…

At one point in the interview, I asked him why he chose to work there. He said, “I use every new job as an opportunity to level up the people around me. I liked the team at my last position, but I liked the team here even more.”

That idea – using each new job as an opportunity to level up people – stuck with me.

It’s important to identify new and interesting opportunities. However, the #1 reason that people leave jobs isn’t because of the lack of opportunities; it’s because they did not like their boss.*

*Based on a factual old wives tale.

Leveling Up the People at CREx

Our first CREx Software team photo

I cofounded CREx because I wanted to level up the people around me. Yes, we solve a huge problem for a large market. Yes, I couldn’t go another day without solving that problem. Even more yes, I had worked in environments where I didn’t enjoy the people and couldn’t wait to work in a more welcoming, inclusive space. I wanted to choose the people that I worked with.

What did leveling up the team at CREx mean for me?

  • Remembering that we are people first and then employees and treating each other as such.
  • Supporting each other in non-work endeavors.
  • Being inclusive and intentional about having a diverse team.
  • Having reliable team members who get our work done based on goals, not on the outdated 9-5, M-F schedule.
  • Good vibes only. We all go through tough times and will support each other; most days, we aim for positivity. Startups are hard enough without any Negative Nancys.

You could say this is having a good culture. I say this is common sense.

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On Knowing What Advice to Take and What to Tune Out

As a startup founder, you will be inundated with advice and opinions. Here’s how I learned what advice to take and what to tune out. 

Examples of Advice to Tune Out

To start, let’s review a few examples of advice that I chose not to take.

As a female founder, you’re never going to raise money. I saw a woman who had more experience than you pitch to dozens of investors and not get a call back. I walked in, pitched, and got $15 million. You should get help.

This quote was from a guy who wanted to sell me on his services to fundraise for our business. His angle was clear. He would benefit from being labeled a “cofounder” and getting that level of equity without doing any work for the business other than fundraising. Don’t get me wrong; most business should highly value fundraising. However, it’s rarely worth giving up a substantial portion of your company.

I don’t like the colors of your branding. It’s too bright and will turn off potential customers. Your firm name is too close to another tech firm too. You should consider changing both of those.

I actually received this advice from a few different investors. Each gave this comment with the angle of if we chose to work with them, they would use their resources to help us with our branding. 

And for the record:

  1. Our website ranks in the top 5 in Google for the keywords important to our business.
  2. I have yet to hear a prospective customer say that they wouldn’t go with us because our colors were too bright and our firm name wasn’t good enough.

Lastly, here are a few pieces of advice that I received prior to cofounding CREx Software.

You have more talent in your pinky finger than I ever had. But you don’t have what it takes to start a business. You should stay in your current role.

You can execute better than anyone I’ve ever known. But you don’t have good ideas. You should focus on execution and let someone else create a business.

I always saw you in this [other] role. You should do that. I can’t support your decision to do anything else.

These are real words that were said to me by my mentors and former colleagues.

I could have believed them. Could have let them stop me. I didn’t.

Instead, I used their words to fuel my desire to start a business. To lead the life that I, Jen Tindle, wanted to live. Not the path that they had mapped out without consulting me.

It’s tempting to take advice from people you respect, even if it means giving up your dreams. Trust me, you are the only person in this world who will always prioritize yourself. Take advice with a grain of salt and understanding of how someone’s advice to you could positively impact them.

As Taylor Swift wisely said, “People throw rocks at things that shine.”

Photo taken after my first pitch competition with HearstLab Ventures

Examples of Advice to Take

Now, here are a few examples of advice that I chose to take. 

Once you have a C-level role, no one can take that from you.

The CFO at one of my first PwC clients gave me this advice. I share it with others to this day. Some people enjoy the predictability in climbing the corporate ladder at large companies. However, you have a small probability of making it to the top. If you want to increase your chances of becoming a C-level executive, you can take an executive role at a smaller firm. Then, you can grow your career by taking C-level positions at larger and larger firms.

I opted to cofound a startup because my former boss told that advancing to the next level in my career would take “many years”. Now, I was already bored at that job. I certainly wasn’t going to wait for the next challenge.

People buy from other people, not businesses.

I can’t remember who gave me this advice. If it was you, please let me know! This is some of the best advice that I ever received for our business. While we sell enterprise B2B software, we operate in commercial real estate, an industry that’s notoriously driven by relationships. Now, I have always been good at cultivating in-person relationships. However, I did not have a strong online presence. 

Many well-meaning colleagues suggested that I become more active on Twitter or LinkedIn but without a reason as to why. Here’s the why – people will buy from the business because of YOU. I chose to craft a profile that speaks about my journey. That seemed to resonate the most with my connections. Regardless of industry, a strong, high-quality online presence will always benefit your career.

Explain what you do in caveman speak. Most people’s attention span is too short to listen or read much.

I paraphrased this quote from “Don’t Make Me Think” by Steve Krug. While the author intended it to be general advice for designing a website, it’s amazing advice about most anything that you need to explain. If you tell people what you do in a common sense tone and language, they will more quickly understand. And if they’re interested, then they’ll ask follow-up questions. And if they’re not interested, then you can wrap up the convo and save both of you time.

Have confidence in yourself and take it one day at a time. It is not the endpoint that’s important, but enjoying what you are doing every day of life on Earth.

I absolutely love this advice from my Dad. He wrote this in a letter to me that I read often. As a startup founder, you have good days and bad days. On the good days, you’re filled with hope and excitement about your company’s prospects. On the bad days, you’re wondering why you quit your stable job. “Are you really smart enough? Driven enough? Is this really a problem that needs to be solved?” The devilish voices in your head are nonstop on the bad days, and it’s hard to stay confident. I try my best to focus on enjoying each day even if it’s a tough one because I know that we’re doing our best. 

Note the critical last piece of his advice, which more succinctly is: Love what you do. If you are a founder and not die-hard passionate about the problem you solve, trust me, one of the bad days will eventually get to you. Then you’ll decide to pack up your proverbial bags, sell or acqui-hire if you can, and go back to your stable job. You must love what you do, or you won’t make it through.

Lessons Learned Between the Two Types of Advice

The key differences between these two types of advice are simply this. Good advice is typically:

  1. from insightful, well-thought-out observations and
  2. not self-serving in any way.

Beware of any advice that starts with flattery. It’s probably self-serving the advice-giver. 

When someone suggests that you do or change something, think first about how much thought they put into those suggestions. If it seems thoughtful and insightful, then think about whether you taking their advice will benefit them in any way. 

In some cases, good advice does benefit the advice-giver. In those scenarios, by all means, go for it! Don’t let mutual self-interest stop you. In fact, that can be a wonderful way to work with friends. 

However, if the advice is NOT well-thought-out AND the individual is self-serving, run. Run as fast as you possibly can and don’t look back.

Take my advice for what it’s worth. 😉 Hopefully a lot someday!

Am I taking this advice or not? I mean, it is from a pay phone...

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To Raise or Not To Raise?

To raise or not to raise, that is the question. If you’re asking this right now – in early 2023 – the answer is most definitely do not raise if you can help it. Investors are like sharks in the water. Now, a couple of years ago when we started CREx, the market was very different. We had to choose whether to bootstrap our business or raise money for our idea. If you ever wondered, “Should I raise money for my startup?” and you’re an early stage SaaS tech startup, this post is for you.

Should You Raise Money for Your Startup?

We’re taught that in order to have a successful startup, you need to raise money. You have to convince investors that your idea is so great that they must get in on the ground floor. And venture has grown as a result. Over the last decade or so, venture terminology expanded. There’s now a “pre-seed” stage and so many series that you need to practice alphabet bingo with your kids/ friend’s kids before even thinking about raising. 

What most early stage startup founders are told...

Many people will tell you that if you can raise, you should. I’m here to tell you that it’s okay if you don’t want to raise. In fact, many incredible businesses were started by founders who chose not to raise, like Sara Blakely from Spanx.

How We Thought About Raising

At CREx, we chose not to raise money for our early stage startup. Now, there are many factors beyond what I describe below. You also may look at angel or family office investment, which is very different capital from venture. Here was our rationale for not choosing to raise venture (at least, not in our early stage).

  1. We finally gained control over our professional lives by starting a company. Why would we want to give that up? Investors essentially become your new bosses. You report to them with at least some regularity, and they will eventually take money out of your pocket.
  2. How valuable do we think our company can be? If it’s valuable, shouldn’t we try to self-fund?
  3. Because we were first-time entrepreneurs with an early stage startup and little traction, we could not dictate investment terms. We already had revenue and were told that we “can’t” raise an angel round (this is not true, by the way). Based on the limited conversations that we had, fundraising for venture was going to be a lot harder for us. Many venture firms viewed proptech (property technology aka real estate software) as overinvested and business intelligence as unsexy (also not true per predicted growth). Our startup, CREx, is at the intersection of those two industries. Now, perhaps we spoke to the wrong investors. 
  4. Regardless, women and minority led companies don’t have a great track record for landing VC money. We learned quickly that fundraising would take us longer than other founders. For example, I pitched to one VC that we were raising a $3M round with our annual recurring revenue (ARR) and a strong customer pipeline; we about doubled our ARR a month later. He said that he would only be interested in a $1.5M raise.  Then, when I told him the other VCs we were talking to at $3M, he said to please send him the deck and he would consider it. 🙃 Not only that, I attended a happy hour event for founders and VCs a couple of weeks later. I spoke to two white, straight male first-time CEOs who were raising a $3M seed with less ARR than we had! And they already filled half of their capacity! Smh.
  5. We had two separate consulting jobs that paid us a decent amount AND, more importantly, gave us massive insights into our product. If you can do this to self-fund at the beginning, do it and don’t look back. You will gain invaluable insights into what prospective customers want while getting paid and keeping ownership of your startup.

Now, scratch items 1-5 above: if we did not have the opportunity to get paid while learning about customer needs, we would have still needed to raise money for our startup. This may be your scenario. If you know that your startup is solving a legitimate problem and will create value, then raising money for your startup at the early stage is an absolutely valid path. And at some point in the not too distant future, we may opt to raise. Our goal is to only raise when we can dictate the investment terms. Inshallah!

Advice to Early Stage SaaS Founders

My advice is this: enjoy not having a boss for as long as you can. For female and minority founders, raise money for your startup only when you have to. OR better yet, raise when you want to because you get to dictate the terms.

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How to Vet a Cofounder

Business at first phone call. That’s how I describe meeting my cofounder, Vimal Vachhani. Our skill sets complemented each other perfectly. Not only that, we wanted to solve the same problem based on our own unique experiences. Then, we found that we truly enjoy working together. Our personalities couldn’t be more in alignment. However, Vimal isn’t the only cofounder that I’ve had, and it hasn’t been smooth sailing for me in the cofounder department. In this post, I’ll share a few tips on how to vet a cofounder.

1) Do a short project together.

If you’ve never worked with your prospective cofounder before, I highly recommend doing so before you agree to grow a business together. Cofounding a startup ties you financially together. You wouldn’t get married without dating the other person for  a while, right? Think of this project as your opportunity to “date” and see if you’re a good fit for each other.

When Vimal and I first met, he was ready to start a data integration and analytics business. His background was not in data visualization though, so he reached out to our mutual friend, Christine. Christine specialized in analytics for real estate but had recently transitioned to banking. While she wasn’t interested in building reports, she thought that I would be.

After Vimal and I met, we knew that we wanted to work together long-term but we opted to set up our initial work together as a trial run consulting project. This allowed us to 1) confirm that our work personalities were compatible, 2) confirm that we were both technically capable, and 3) have an out if we decided that we didn’t want to start a business together.

2) Talk about your lives beyond work.

Starting a business means giving up most of the separation between work and your personal life. However, you must maintain a life outside of work if you want to keep your sanity and your existing relationships. You need to discuss what’s important in your life outside of work so that you can help each other make time for that. 

When Vimal and I met, we’d both been through a lot personally. We were restarting our lives, in a way. Vimal had even moved cities and was finding a new group of friends in NYC. We both wanted to make time for self-care while making new friends and spending time with old. By having these conversations up front (and ongoing), we made that happen.

Your cofounder is your support system. If you can’t rely on them to help you prioritize what’s important in your life, then you shouldn’t trust them to run a business with you either.

3) Ask for references.

This is the most critical step in how to vet a cofounder. I’m going to stand on my soapbox for a minute. Asking for references is an absolute MUST for female founders. Let me share my story to explain why.

Tldr: I had a bad experience with a cofounder who was more interested in sleeping with me than he was working on the business together. I learned the hard way that references from other women who have worked directly with your cofounder are critical. 

Before I quit working at the private equity real estate firm, I knew that I wanted to leave to start a business. I didn’t know what yet. Fortunately, I had a few confidantes that I trusted and could bounce ideas around with. One in particular loved the idea of me starting a business. I remember the phone call vividly. Let’s say my confidante’s name is Jesse.

Jen: Hi Jesse! How are you? What’s new?

Jesse: Oh not much. It’s been crazy since the pandemic hit, but we’re all hanging in there!

Jen: I believe it. It’s been crazy around here too! We’ve finally gotten back to a sense of normalcy. 

Jesse: Oh yeah? What were y’all doing that was keeping you so busy?

Jen: It’s our investors. Ever since we started reporting more detailed information to them, they want and expect more. Our executive team too. Which I totally get and am happy to do, but honestly it feels like the same drill over and over again. I wish we had the ability to automate it more. Confidentially, I’m ready for something new.

Jesse: That makes sense. What are you thinking?

Jen: Honestly, I’ve always dreamed of starting my own company. I was –   

Jesse: If you have a single entrepreneurial bone in your body do it. 

Jen: You think so?

Jesse: Yes. If you don’t, you’ll spend the rest of your life regretting it and wondering “what if.” I’m so glad that I started my own company, and I can’t imagine doing anything else. If you have any desire to start something, you should do it now. [This was very good advice that I second!]

Jen: Huh. Good point.

Jesse: What kind of business are you thinking?

Jen: Well, what I know best is analytics for commercial real estate. Maybe something in that space? I had so many people talk to me after that PREA conference that it seems like there’s a need for it.

Jesse: Tell you what. Why don’t you build this using my properties? And I’ll fund you?

Jen: Seriously?

Jesse: Yes. Give me your pitch when you’re ready. Take your time.

Jen: Okay, great! Will do.

I quit my job and we started working together. We were building integrations and analytics for a completely new property type to me, and I was learning a ton. Eventually, we scheduled a trip to connect in person to discuss details. During that trip, my then cofounder made several passes at me. I didn’t know what to do, so at first, I just played it off. When it became clear to me that starting this business together was predicated on us having a relationship, I got out. Maybe I should have seen the signs earlier? Or perhaps I was inadvertently leading him on? Who knows. What’s important is what I learned: make sure your cofounder will treat you with respect and sincerely wants to start the business with you.

Let’s go back to when I first met Vimal for a proper example of how to vet a cofounder. Our mutual friend, Christine, knew the details of what happened to me. She called several other former female coworkers of theirs (and a male one or two, if I recall) on my behalf. She asked them what their experience was like working with Vimal, testing for any potential red flags. Because Vimal is a wonderful human, there were none.

I cannot tell you how much I appreciate Christine looking out for me. This is what women supporting women looks like. Get your references, ladies. And guys, you should do this too if for no other reason than to ensure your new cofounder won’t screw you over on something down the road. Keep in mind that you’re interviewing each other for the job of cofounder. References are a normal part of hiring.

Recap: How to Vet a Cofounder

To recap how to vet a cofounder, make sure that you do a project together first, talk about your lives beyond work, and review each other’s references. If after all of that, you still want to work together… well then, you just might make something beautiful. I can’t wait to hear what you start!

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How to Become an Entrepreneur

Have you always dreamed of becoming an entrepreneur? I did. And I made it happen. In this post, I will tell you how to become an entrepreneur based on my own personal experience.

Let me tell you a story. There was once a girl who decided to get her masters in accounting. She did so well in her accounting undergraduate coursework that the professors let her skip some classes in favor of other MBA coursework. Now, this girl always dreamed of being an entrepreneur. She was only getting her masters in accounting because it was supposed to be a good background for running a business. As soon as the fall course schedule arrived and she saw the “Intro to Entrepreneurship” MBA class, she signed up immediately. She was practically giddy with excitement! 

Finally, the first day of school came. She barely restrained herself from skipping into the “Intro to Entrepreneurship” classroom… but only barely. It never occurred to her that as the youngest in the class, she ought to be self-conscious. As the professor shushed the room and approached the podium, she sat up straighter, eager to learn. 

“Why do you want to be an entrepreneur?” the professor asked.

Her hand raced to the ceiling. 

“Yes?” the professor asked as every head turned towards her.

“I want to build something bigger than me. To create something that’s meaningful and changes lives.”

A pause. 

The first laugh was big, the kind of belly laugh you hear after an unexpectedly good joke. And then another jolt of laughter, and another, and another… until finally the professor yelled at the room, “QUIET!”

“What a dumb answer,” one of the MBA students said.

“Oh? And why do you want to start a business?” the professor asked.

“To make money, of course,” replied the MBA student.

“Ah. Money will only motivate you for so long. She” – as the professor pointed to the girl – “has the right idea. It won’t be easy being an entrepreneur, and if money is your only motivation, then you will surely fail.”

In case you haven’t guessed, that girl was me. That was the first time I expressed my desire to be an entrepreneur to a large group of people, and I was literally laughed out of the room. What I’d like to say to that room full of MBAs is: who’s laughing now? I did start a business, and we built it on the premise that we’re automating boring tasks that make people’s lives better. And in the process, we’re gathering even more data that improves (and will eventually automate more) decisions. 

I shared this story for two reasons: 

  1. If you’re starting a business solely for the money, stop now and go back to climbing the corporate ladder.
  2. The critical first step in any entrepreneur’s journey is the toughest: identify a problem to solve and by solving it, create value.

Identify a Problem to Solve and Create Value by Solving that Problem

Here’s how I identified a problem to solve. From the few conversations that I’ve had with prospective investors, I’m told it’s the ideal founder story. Take that for what it’s worth (which is hopefully a LOT of money someday).

  • I started my career in public accounting, as planned. I gained invaluable experience about the financial aspects of running a company.
  • After I essentially aced the CPA exam and won a national award for doing so, I leveraged that to land a job in real estate. I’d heard that it was a good, stable industry to be in. Now, to be fully transparent, I completely lucked into working at a private equity real estate firm. I had no idea that most people have to slave away for years in investment banking first! The PE firm’s hiring committee were mostly ex-CPAs and impressed by my CPA exam scores. Luck + skill for the win.
  • Once I started at the PE real estate firm, I immediately realized how spoiled I’d been with the technology at PwC. My first task was to manage a team of interns typing up PDF documents into massive Excel spreadsheets. I then combined those spreadsheets into more spreadsheets. It was painful. Like I physically hurt to think about it now. We had to do this because of the firm’s setup. We were what’s called an allocator. We partnered with operators via joint ventures, and those operators managed the day-to-day of the real estate that we jointly purchased. This meant that all of our data lived on other firm’s systems. And those systems didn’t have a standard way to send us our data.
  • Fortunately, I knew a thing or two about programming. My older brother is a software architect, my younger brother is a data engineer, and my romantic partner at the time was a front-end developer. I was surrounded by people who knew how to automate these things. So I polled the audience. Asked what tech I should use to make this better. Then I bought books, read blogs, and tested code until I automated as much as I could. Identify a problem to solve: check!
  • With the executive team’s permission, I began seeking public speaking opportunities. I was a tour guide in college, and I love having a captive audience for my “Dad” jokes. Plus, it seemed like my colleagues who spoke at conferences were getting promoted faster. From what I could tell, the data we gathered and were visualizing was unusual in the industry and seemed like a good thing to talk about. And oh boy, it was! Eventually, our firm had the opportunity to present at PREA, which is one of the largest real estate conferences in the U.S. I was chosen to speak. Afterwards, I was inundated with emails, LinkedIn messages, and calendar invites. This was the first time I realized that having better data would create value for other real estate firms. Check and check!

Kayo Women in Real Estate (my first panel). What a powerhouse group of women!

Figure Out How to Solve that Problem Better Than the Competition

What I didn’t have was a better way of solving my PE real estate firm’s problem. I’m the first to admit that I’m a self-taught developer. While we had grown the data team to an awesome group of people, we were limited in that none of us had ever worked as a data architect, or even better, a data architect in real estate. We were doing the best that we could with the skills that we had. Our processes worked well for a single firm. However, they weren’t scalable. 

Let’s make some noooiiiiiiiiseee! Shine those bright lights on over to my cofounder, Vimal Vachhani!

A mutual friend introduced Vimal and me. More on this story later. Meeting Vimal, well, that was business at first phone call. Our skills perfectly matched. He was a seasoned data architect with 17 years total work experience and 10 in real estate specifically. Vimal knew exactly how to write code that pulls data out of archaic real estate software and make it into a usable data model. He wanted to start a business because he felt like he wrote the same code over and over again, meaning that it could be a SaaS solution. My dream come true! Plus, I knew the metrics that real estate firms wanted to monitor as well as generally how these firms work. We were the perfect fit.

At the PE real estate firm, I managed the tech budget and interviewed vendors. This meant that 1) I knew how much real estate firms were willing to pay for our software 2) I’d seen and/or tried most of our competition. With our powers combined, I knew we could build a better, more affordable solution.

How to Become an Entrepreneur

Investors like our story because we both had direct experience with the problem that we’re solving, and we know firsthand how it creates value for our customers. 

My advice to aspiring entrepreneurs is this. Go work in the industry that you’re most interested in. Take an entry level job doing menial work. Figure out how to automate it. Or, identify problems that cause issues in meaningful processes. Then, figure out how to eliminate those problems and issues. It’s not glamorous, but it does work.  

A Note on Passion

As an aside, you must be passionate about the industry or the problem. That will make the tough days easier. I’m passionate about automating data gathering jobs in real estate because those jobs are primarily held by women. I believe that if we automate these tasks, these women will have to be given other, better opportunities. Given the focus on diversity, firms need to keep women and minorities employed. After automation, women will have the opportunity to demonstrate their value. This is based on my personal experience. I created opportunities for myself at my former PE real estate firm, and I plan on creating them at as many other real estate firms as possible.

What Are You Waiting For?

Go start that dream business! Or as a first step towards your dream, get that menial job in an industry you love! 

As Hipolito said, “We pass the time of day to forget how time passes.” Don’t pass the time aimlessly. Build your purpose. Work every day towards your startup goals. I believe in you. Believe in yourself, too.

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How to Start a Startup (As a Woman)

It’s hard to start a business. Full stop. 

It’s even harder if you’re a woman. 

That’s why I’m writing this blog. I will share all of the nitty-gritty details of how to start a startup as a woman. Whether you’re an aspiring female founder, a female executive facing similar challenges, or an ally who wants to understand and support your colleagues, this blog is for you.

Together, we’ll explore the many challenges that all founders experience. We’ll also focus on the less-talked about challenges faced by many female founders. Throughout each post, I’ll share my strategies for overcoming these obstacles. While it’s never easy to start a startup, my goal is to let you learn from my experiences with the hope that you’ll have an easier path than me.

These are the challenges that I have faced in the nearly two years since we started CREx. As a precursor to the stories that will follow, let’s briefly talk about each of the female-specific ones. I promise to share how I overcame them later.

Getting Shafted on Funding

You may have read that women receive less than 2% of all venture funding. Many of my male founder colleagues receive millions of dollars in funding before they even have a viable product. Instead, most women need traction and some product-market fit before we could dream of raising that amount of capital (without giving up half the business). And even if we have that, many investors focus on ancillary things, like “You need a better name for the company” or “I think your brand colors are too bright.” Alas, our problems extend far beyond raising capital.

Cofounder or Investor Tries to Sleep with You

In my case, this was the same individual. Some women, such as Whitney Wolfe Herd, may have a relationship with their cofounder that falls apart. Then, discrimination ensues. 

*My current cofounder, Vimal Vachhani, is an incredible human and ally. I had this experience while starting a previous company.

Former Employer Tries to Claim They Own Your IP

Many of my male founder friends have former bosses who so strongly supported their business idea, they invested. That didn’t happen to me. And once again, it didn’t happen to Whitney Wolfe Herd either.

Dressing Appropriately

You may be thinking, “Why is this on the list?” Well, I put it on here because I guarantee that none of my male founders have ever had to second-guess their outfits like I have. Should I wear a blazer and slacks or jeans and a jacket? Sneakers or heels? Can I wear fitted pants or will I be sexualized? And oh boy, did I learn the hard way NOT to wear a dress on a conference panel. Keep those legs crossed, Jen!

Prospective Customers Only Want to Speak with the “Boss”, Your Male Cofounder

For some reason, I thought that the letters “CEO” on my title would magically grant me respect. They don’t.

Now, if you are an aspiring female founder, please – don’t let this list scare you away. Instead, let it motivate you. The only way that we even the playing field is by normalizing our existence as successful founders. Let’s do this. Together.

Keep reading to learn more pro tips on how to start a startup as a woman. You’ve got this!

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