Celebrating Diana Aladzhova, winner of Most Endeavorized Mentor for 2024!

Our yearly Mentor Awards recognize the mentors who have made the greatest contributions to our network. The awards are divided into three categories, based on data analysis from 2023, reflecting the following criteria:

  • Hours dedicated to mentoring sessions and supporting our investor network
  • Participation in events and overall engagement
  • Feedback and evaluation of mentoring effectiveness

The categories are:

  • Mentor of the Year – The mentor with the most hours donated in support of Endeavor’s regional and global network and Endeavor entrepreneurs.

  • Most Endeavorized Mentor – An Endeavor ambassador who actively contributes through introductions, being an ambassador, or otherwise demonstrating commitment to our mission.

  • Dare2Scale Mentor – The mentor with the most hours donated in support of the Dare2Scale program, including workshops, interviews, mentoring sessions, and other activities.

Meet Diana Aladzhova, entrepreneur, investor, Endeavor Mentor, and the winner of the 2024 award for Most Endeavorized Mentor for her contributions in 2023.

From banking to venture capital, Diana has built a dynamic career at the intersection of finance, investments, and social entrepreneurship. As a partner at Silverline Capital, founder of CFO Insights, and co-creator of impactful ventures like Box to Remember, she embodies the power of combining professional expertise with a passion for mentorship and sustainable change.

This interview was an exciting one for me—not least because of the cool under-desk bike she keeps in her office. Diana let me try it out, and I can confirm that she uses it a lot—the kilometer tracker was off the charts!

Back in the CFO Insights’ meeting room, one of the two businesses Diana has founded, we sipped our coffees and had a chat.

You spent your high school years in a German-language school and then went on to earn degrees in economics and finance.

“I didn’t choose my high-school because it was humanities oriented. Back when I was applying it had the highest likelihood of students securing employment or achieving success in their careers after graduation. Which, when you are thirteen, seems like a great choice. Most of the people I studied with weren’t necessarily in a humanities stream. I am more of a math track, my twin sister was a humanities track, both of us studied in the same school but took different classes,” explains Diana.

Do you still use German?

“To be honest – no.” She goes on to explain that it’s a good language to learn, and that in general her opinion is that people should learn languages, it just so happens that in her work she doesn’t need to use it.

 

Humanities seem to be a red thread guiding everything you do—from Box to Remember, the other business you founded, to the social entrepreneurship class you teach at Sofia University. You manage to combine both finance and the humanities.

“I think it comes from a sense of belonging. Belonging in Bulgaria, for example.” Diana explains that her homeland has been an anchor point—along with her family, friends, and society as a whole. “In order for a person to feel good in the place they have decided to put down roots, they need to feel useful. And the way I feel useful is to have value add for our society. Here’s the question – what are the things that add value to our society and I can do? This will be different for every person. For me, it was social entrepreneurship, ever since I discovered it fifteen years ago.”

Was social entrepreneurship popular back then?

“I wouldn’t say so. It was defined in different ways. What didn’t change, though, is that social entrepreneurship combines business logic with the social element of value add to society. And this is the first thing that combined both of my vocations – finances and social activities. I wanted to find something that combined both of these, so that they did not exist separate of each other, without any synergies.”

Diana tells me that this realization came to her around the time she moved back to Bulgaria from London, where she earned her Master’s in Finance and Private Equity. While mentoring entrepreneurs focused on different social causes, she noticed a recurring issue—social initiatives tend to have one-time, unrepeatable impact, heavily reliant on donors. Diana wanted to figure out how to create a social initiative that wouldn’t depend on outside funding but would have a sustained impact.

“This is the essence of social entrepreneurship. To create a business with a social cause,” she explains.

To further this mission, eight years ago, Diana began teaching a “Social Entrepreneurship” course at Sofia University, in collaboration with the NGO United Ideas for Bulgaria, where she serves as chairman.

In an interview for Darik, you mentioned that Box to Remember started as a course project—a way to show students the potential of social entrepreneurship. We also discussed how the young people in your course are full of energy and enthusiasm to create. Have any ideas from the course turned into actual projects?

“There are a lot of great ideas that come out of the course. But, let’s not forget that there is massive amounts of work to be done between idea and execution. Not many people move from one to the other, in general, let alone from the course.”

 

As an investor, have you considered funding any of these ideas?

“I would, for sure. But before that the team has to have a value-add mindset, both for their clients and society at large. Social entrepreneurship has two target audiences – the people you sell to, and the beneficiaries in favor of whom you are acting. I would need to see that the team is thinking in this direction, that they have an idea for a product, that they’ve made the first steps. If they have all these things and come to me, I will always help them.”

 

What do you think is the connection between investment, finance, and social entrepreneurship?

“The connection is in the value-add mindset. You have to wake up with the readiness to solve a problem. Problems are diverse, and so are their solutions. So, you can go in many different directions. But most of those directions have synergies between them. I’ve found, in my life, in my experience, that nothing is in isolation.”

Diana gives several examples — how, while studying finance at LSE, she discovered social entrepreneurship, and how many of the case studies she gives her students come from real companies she works with. These are the synergies she sees—how seemingly different paths and personal interests intersect to create opportunities for innovation, learning, and impactful solutions.

 

Mentorship seems to be another key theme in your career. During the Dare2Scale workshop, you mentioned that you almost become like family, with companies that you are in long-term partnerships with, where both parties are dependent on each other resembling the dynamic. with the companies that enter Silverline’s portfolio. That’s also a type of mentorship. What does mentorship bring you?

“Stress,” she replies, laughing.

“The investor role is to help the companies create an organization within that’s aligned with the strategy that they’ve invested in. So, our role is more than just mentorship, as there is a lot at stake. You have to be fully immersed as it is a complicated process – organizational structure, emotional states of the team, inner team communication, discipline, etc. Therefore, we spend a lot of time with our companies.

A mentor, I’ve always thought as, a person who is outside of the organization. A mentor comes, shares the necessary knowledge and leaves. While investors enter the organization and leave when the investment is fully realized. It is a whole different type of professional relationships that needs to be built.

I would say they are on different levels. The people closest to you are, of course, your family, but on second and third place come the companies we work with, for sure,” she laughs.

“We build trust this way. Without trust and transparency nothing else matters.”

 

After a short explanation of what a mezzanine fund, such as Silverline, is, we continue discussing mentorship. What keeps Diana driven, after so many years of mentoring entrepreneurs, is what she gets from the experience — learning. To her, mentorship is more than just sharing experience. Diana says the companies she mentors always provide her with new information and perspectives that help broaden her horizons.

“I have a special place in my heart for companies in the healthcare field, because I think that there is a huge need for such innovation. I mentor three companies in this sector. The challenges they face are complex and multifaceted, they cannot be compared to challenges that companies in other industries experience. When I work with such companies, this gives me an insider’s view into where the challenges lie. Why some ideas work and some don’t. So, when a company in this sector comes to seek funding from us, I can quickly analyze what their business model is, what stage they are at, what their business plan looks like, etc. And I wouldn’t have this ability if I didn’t mentor such companies,” Diana shares as an example. She explains that while companies choose her as a mentor because of her experience and expertise in certain fields, mentoring also helps her build strong connections with professionals she can later turn to for advice.

This fits well with what we previously discussed—how you believe that giving back isn’t exactly “giving back” but rather “give-always.” I’m a big fan of this philosophy that everything you put out there always comes back. Woman to woman, I can’t help but ask—what is it like working in finance and investment?

“The truth is it’s never bothered me that I’m a woman in my industry. Not because there weren’t challenges, but rather because being a woman helped me. Helped me be more motivated, when I realize it would be harder to achieve something that motivates me to be even more prepared, to give even more of myself. Especially in the first years of your career, at an industry level, there is a sort of underestimation, and this allowed me to achieve more than I would have if I were constantly given undue credit.

I have a story from four years ago where I entered a meeting and was viewed as the secretary coming to ask if anyone wants a coffee. Until we all sat down at the table to negotiate. These things happen, but they should not be stoppers. Every woman should believe in herself, shouldn’t give up, and not to take any feedback as set in stone.”

Diana and I discuss imposter syndrome—the feeling of doubting your skills, talents, or accomplishments—which is prevalent among women. Diana explains that this phenomenon has a psychological basis and that she often encounters it in the women around her.

“I’ve never liked this as a way of thinking,” she says, before sharing her approach to dealing with it. “You should stop doubting yourself, and instead call into question the instruments of the given situation. Specific situations typically bring out this syndrome, and when you stop thinking about yourself, but rather focus on the situation. Is what I’m thinking or suggesting the right instrument to deal with the current situation?” This perspective allows for growth and adaptability without negatively impacting self-esteem and confidence.

We talk about not internalizing feedback and situations, with Diana adding that this is extremely important. She explains that when faced with an unfamiliar situation, you should find a way to replace the strong emotion that stress brings—typically caused by uncertainty—with another strong, positive emotion, such as excitement. Any emotion can work, as long as it is positive. Don’t transform it into anger.

 

As we’re on the topic of great advice, I want to ask you one of my favorite questions, which I always ask our mentors—is there a piece of advice you catch yourself giving over and over again?

“This about imposter syndrome is a piece of advice that I always give the women I work with. The case I see very often is a woman, who is an expert in her field, feeling like she is not ready for the next step. Nobody is ever a 100% ready, but you can be ready enough. You should be ready to start, not to finish the task, majority of people when they start something don’t have the knowledge and experience to see it through. And this is where confidence comes to play.

Another piece of advice I give women is to not worry about balancing work and life. I believe that it is absolutely possible to do both. I can’t say that it is easy or that there is a universal recipe how to do it, but it is possible.”

Diana tells me about her two children, who, she says, are her biggest motivators to move forward professionally. Nothing else brings her as much happiness or motivation as being able to build something to leave to them.

“It’s not inheritance, it’s heritage,” she says, explaining that she doesn’t want to leave them material wealth but rather a way of life—to show them that everything is possible, to give them a framework for success. She acknowledges that money is a part of that, but in her opinion, money is the means, not the end. The end goal has to be higher.

Business-wise, Diana says that the piece of advice she gives most often is to focus on the business model. Often, conversations revolve specifically around the product or fundraising strategy.

“I try to explain that you need to focus on the business model first. How will you create enough quantity of the product, in order to scale? Who will buy it? Is your client base big enough? And how does all this come together in your business? A product is not a business. A marketing channel is not a business. I always try and bring the conversation back to the big picture – the business model.”

 

This is relevant to a lot of things in life—focusing on the bigger picture. You talked about work-life balance. Considering how much you do, how do you manage to balance the two?

“The first thing is to properly manage my own expectations. You set goals but don’t try and maximize everything. I ask for help, especially with my kids, especially after they turned one, and especially during working hours.

Even though, maternity energizes me. When I had my first kid that’s when we started Box to Remember, so she came everywhere with me. I had my work meetings at the park, I would have my meetings and then we would play. With my second kid, I had all my work meetings in this restaurant in a park. For close to a year. And it turned out that people enjoyed getting out of the office.”

“Second, this built a lot of trust between us. It also helped me balance my work with taking care of my kids. At the same time, it was accepted by everyone.

This is where managing expectations comes in. If I had the expectation that I will only raise my kids at home or very close to home, this would have stopped me from doing a lot of what I did. Instead, I found ways to make it work. Oh the parks that I have signed contracts in.

I never stopped working even during my maternity. But I believe in finding the middle ground. You compromise on some things, and that understanding gives a lot of peace of mind. If my kids are sick, I take time off. But I am aware of the possibility of doing so, and OK with it. There is always a way to make things work.

Managing your expectations lowers your stress. I’ve come to the realization that even if something doesn’t work out a hundred percent, I don’t feel bad or guilty. If I have done my best and it still didn’t work out, I stop thinking about it.”

Diana’s formula for work-life balance? Managing expectations, making compromises, and managing stress—all while doing something fulfilling and enjoyable.

These lines are filled with so much wisdom. Diana is a true example that having it all doesn’t mean sacrificing — it just means compromising. And there you have it — our Most Endeavorized Mentor inspiring us once again.