From Politics and Film and Other Compelling Stories

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This Is What Happens on Clubhouse…

So what happens when you listen to someone share their story on clubhouse and it’s so powerful and real you can’t wait to hear more? You invite them to do an episode on your podcast and hope they say yes. In this episode I was able to interview Sola Adenakan, co-founder of St8cked media and BrazenTv, which focuses on social issues and putting women and POC behind the lens. Along with her newest project Transmit Media Podcast Network, the first Afro Latina owned social impact podcast network.

It’s a lot going on but she was gracious enough to speak with me and I’m so thankful for it, because her story is also just as compelling as the stories she films.

My name is Jessy Santana and I’m an organizational culture strategist, entrepreneur, mother. This is The Way We Work podcast, where we discuss all things at the intersection of knowledge-seeking curiosity, entrepreneurship and social impact.

Take a listen to the full Interview Here

This is what happens when you let go of fear or the narrative you can’t and just do. Clarity through action and we’ll all be manifesting powerful stories too.

I can’t wait to keep learning about Sola’s work and you should definitely check her out too. At her new project Transmit Media Podcast Network and all of her other incredible work.

This Week’s Rose Bud and Thorn

I am so excited that The Culture-Driven Leader academy is now live! And the first cohort will begin on Feb 15! If you’re interested make sure to check out the site here or on my IG @theway_wework you’ll find more information there.


All of this creating content, entrepreneurship takes a toll on your family and sometimes you don’t even realize how much. Maybe that’s why so many entrepreneurs are divorced. Someone once told me, there is no work life balance as an entrepreneur, you have to choose between work, family, friends, health or sleep. What’s your choice?


After that conversation with Sola, I’m just really looking forward to the rest of 2021, it won’t come easy and it won’t come fast but change inevitable and I just want to work with those that are ready. So if you’re with me, you know what to do.

If you liked the show make sure to like and subscribe and leave a review and don’t forget tell your friends to listen.

Follow us on Instagram @theway_wework or check out the website at

If you have any questions on culture, identity, the spectrum of where we fit in send an email to

Key Take Aways From Web Summit 2020

people on a video call

If you’re interested in the worst case of online misogyny I’ve ever seen professionally- scroll down to the last section.

It Was Good Until It Wasn’t…

If you don’t know the Web Summit conference, you might want to get on board. Luckily for me, it was online this year and I was able to attend from my living room. It’s all about tech, startups, business, and this year- I don’t know if it was me or what but the AI talk was everywhere!

This reaction right here!

If you don’t understand AI, you’re not alone

AI seemed to be a big hot topic at the Web Summit conference this winter and everything from startups and politics were talking about it. It’s the flashy new toy on the trendy tech block.

This is the easiest way to understand it that I’ve come across, it’s data management. Pure and simple. It’s taking heaps and heaps of data and compiling, organizing, and applying it to whatever it is that you want it to do- the idea that eventually it will become an autonomous compiling and applying.

This is the thing I don’t understand- why hide it in secrecy? If you can’t explain to someone in a way that they understand you are creating a level of exclusivity that is inherently discriminatory. If you laugh at someone trying to understand the applications of AI that may benefit their entrepreneurial aspirations- the buck stops there. Right?

I don’t know- something about that just rubbed me the wrong way. Especially when it came to online networking- speed networking by the way that made it good if you weren’t clicking because you didn’t have to and also good in figuring out quickly if you wanted to continue the conversation.

For me, it was a great way to validate some things- I was able to quickly introduce myself and judge reactions to what words I used. (Always a research at heart).

My Online Roundtable Experience

This was fun! I was on a panel on Leading your Organization with Empathy and Abundance. It was riveting- you know I’m a big fan of empathy at work! We had an engaging discussion led by Danielle DeRuiter Williams, from the Justice Collective in the US, on intersectional inclusivity, what companies were doing right in 2020, and what they still needed to be doing moving into 2021.

We covered neurodiversity, flex scheduling, mental health and accessibility! It was a lot for an hour but everyone was contributing left and right and doing so in a way that inspired me! I was so glad to be a part of it.

There were other panels: Inclusion in Tech, AI possibilities, etc. There is so much happening right now in people trying to create change in the tech industry which is amazing to see, but let not the momentum fizzle out.

Even the speed networking mingle, was entertaining- if it was on the verge of awkward at least it was only 3 minutes and if you were enjoying the conversation you had the option to connect and if they felt the same way you would be given each others’ contact.

Some Parts that Always Disappoint

Pre-recorded interviews are boooooring! There’s little engagement unless you count people in the chat complaining about the fact the video was pre-recorded. Once they move on from that there tends to be criticism- no point in keeping it quiet, the speaker isn’t going to see it.

In order to make up for it, there were often Q&As after the pre-recorded session which was live but depending on the notoriety of person, some or most Q&As like Microsoft or Facebook still left much to be desired. Which was understandable, it’s not like the audience always get their questions answered in person at the conferences.

The Greatest Disappointment

This was something that although it’s talked about in many circles I had yet to experience it, not having had to pitch in front of investors before. Throughout the conference, several startups pitched their ideas throughout various portions. There was one block that was all about the 40 word pitch. Man, condensing your startup’s business into 40 words? That is a feat unto itself.

There was a healthcare startup led by a male founder, who pitched to an all-male judge panel. Now that is not the biggest issue, I get the numbers are not in our favor for much diversity in VC firms but the kicker was that after the healthcare application and the judges questions were presented i.e. their interest in the startup or their reservations.

The second startup was a female founder speaking on recycled fashion- and immediately the mood changed for the judges. They were no longer jovial and with an air of ease. The founder, albeit was very excited about her venture and it showed, the judges’ response? Make an off-putting remark about being a zodiac sign- apparently making a joke in some way of the founder?

It was the most disgusting display of professional misogyny I have ever seen!

It was like they forgot they were on-screen and had slipped into private boys clubs where girls weren’t allowed and with a clearing of the throat remembered where they were. They then proceeded to ask completely ridiculous questions predicated on the fact that none of them knew anything about fashion-duh! I could tell by their polo-induced comas. And the second hesitation was that they weren’t sure of the validity of recycled fashion and whether or not people would be into it.

Really? Ever heard of Rent the Runway or Posh? and others I’m sure.

It was as if they heard fashion, saw it was a woman and grumbled to themselves, “Oh no no no, can’t touch that- fashion doesn’t affect everyone.” I’m hearing the voice of that Oh no no laugh meme that was flying around a while back.

It was like seeing a real life pig fly across the sky- I’d heard the expression but didn’t believe it really existed.

Now I’m not an expert on body language but since being at home for 9-10 months, a year- I’m not sure. But it’s made me super paranoid about my background and surroundings- something I take note of while I’m on a call- oh and how I’m presenting myself, if I’m not the one talking. No booger scratches here please 🤦🏽‍♀️!

Other than that it was a great opportunity to learn all about Europe’s tech, its limitations and opportunities and to meet and speak with people I normally would not have come across. It’s always a learning experience I love.

If you want to stay connected, check out our social on IG and Twitter @theway_wework and if you have any questions email us at

Would love to hear from you!

Yours in kind,

Jessy Santana, Founder & Principal, The Way We Work

5 Conversations to be having with your staff- Now!

This year has been full of deep change, some necessary others out of our control, but when we look back at this year I don’t want to say this was a lost opportunity. That we learned to survive yes, but that’s it. We didn’t learn to have hard conversations about what kind of culture we want to create within our corporate walls.

Instead, let’s take this opportunity to do just that! Learn to use this moment, full of change, uncertainty and potential to create and strategize what we want the future to look like.

So here are 5 conversations you should be having with your staff- right now! Don’t wait until 2021 to figure out how to move forward. By then it may already be too late!

1. What are our Problems?

This is an open call question that requires input either as a town hall, if people are feeling brave or as an anonymous survey. Please, please don’t single your employees of color to answer questions about race, identity, etc. The intention may be good, but the optics isn’t. While this may be an opportunity for open discussion and dialogue, you want to make sure you have the resources and the guidance you need for this happen, without the learning happening in one direction. 

2. Who’s Leading the Charge?

Do not assume because someone is of a marginalized group that they want to be a part of the conversation. For some, the heightened scrutiny and attention may seem more like tokenism and will in the end be unproductive rather than the well-intentioned level playing field it needs to be. 

3. Who’s at the table? 

If you don’t have a Diversity and Inclusion position and you’re not sure where to start- find a resource. Whether it’s a consultant, a webinar, or even a book club, or fill the position with someone that knows what they are doing. Someone who has an interest is a great start, but if you’re promoting from within make sure that they have the resources in order to make their position impactful. 

4. Do we need a full-time position?

I know it may seem a big undertaking for many companies in transition but the hard truth is that most companies need the position and if you’re not ready yet, to find a consultant they can work with that will guide you in the direction you should be going. Diversity and Inclusion is not new as a position but as we know most positions don’t have the full authority to exact change throughout an organization, or their positions are relegated to HR-centered positions (I have my own theories as to why this is wrong) but the brief is that in order to create in Inclusive environment, there needs to be a re-thinking of what the company’s strategies, processes, and operations need to do in order to change company culture. That may require more than just a department-specific function. 

5. Are We Ready to get in the Trenches to Make Inclusion a Priority? 

Like all departments of a company, I believe inclusion is just as important. If things go badly, you don’t cut operations or strategy, you learn to pivot. When 2020 changed how most traditional firms work, we didn’t just shutter our doors and give in. We paused, created a plan of action and dealt with the changes we could control. The same goes for Inclusion. It’s not a band-aid fix to a moment, it’s a long process that creates impactful change throughout an organization for years to come. It can lead us forward as a leader in our respective industries or like many that will not survive 2020, it can be the resistance to change that will ruin us. We cannot pretend we can go back to business pre-Covid, that past no longer exists. What we can do is understand this moment and create the innovation and strategy that will propel us forward through 2020 and beyond! This is not short-term work, it’s life’s work. 

We have a lot of work to do, and it’s going to take a lot of un-learning, learning and uncomfortable conversations but if we’re willing to put in the work, creating a more inclusive and innovative corporate culture is within our reach!

Yours in kind,