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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 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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