Zero To A Hundred – Episode 38: Business Growth Through Relationships With Frank Mastronuzzi

Zero to a Hundred - Jarrod Guy Randolph | Frank Mastronuzzi | Relationships

 

Accelerators! 🚀 Ready to unlock the secrets to sustainable business growth? We’re joined by Frank Mastronuzzi, founder of Punch Financial, who has helped over 150 companies secure more than $850M in venture funding. Frank shares how to build key relationships, create recurring revenue streams, and prepare your business for long-term success. Whether you’re navigating startup life or scaling an established company, this episode is packed with insights to take your business to the next level! 🎯

What’s on the Menu:

💼 How to nurture relationships that drive revenue and opportunities.

🔄 The power of recurring revenue to increase business value.

📊 Strategies to maintain financial clarity and avoid common startup mistakes.

Why Tune In?

Frank’s practical advice on relationships, finances, and leadership is invaluable for entrepreneurs looking to create a business that thrives—even in challenging times. Don’t miss this masterclass on resilience and growth!

💬 Gem from Frank:

“Your financials are the resume of your business—make them impeccable.”

Get in Touch with Frank:

📧 Email him at Frank@PunchFinancial.com or connect on LinkedIn and Instagram at Punch Financial.

Don’t miss out—hit that subscribe button and let’s take your business from zero to a hundred! 💥

 —

Watch the episode here

 

Listen to the podcast here

 

Business Growth Through Relationships With Frank Mastronuzzi

Frank Mastronuzzi, thank you for joining us on the show.

Thanks for having me, Jarrod.

Introducing Frank Mastronuzzi

This is going to be an interesting conversation for us because you do a lot, but it’s all focused on the same thing. Before we dive into the technical aspects of the financial management of the company, let’s talk a little bit about your background and how you have built Punch Financial into the success that it is now.

Good question. I did take a traditional approach. I started with Deloitte, working in Deloitte Audit in New York and Chicago. I had financial services, insurance, and manufacturing. I had clients like Merrill Lynch, Church & Dwight which is the Arm & Hammer brand, Princeton University, CNA Insurance, and Discover Card as a client. I had a good breadth during my tenure in public accounting. I did three IPOs, and I got a full breadth in a short tenure.

I followed one of my senior directors to Motorola’s internal audit, which is where I fell in love with technology. I got a good taste of how technology runs globally. I knew I wanted entrepreneurship and tech. I applied to a bunch of schools, but I wanted one that had a decent life outside of the college university. I went to the University of Texas at Austin for wonderful work. We had some amazing football seasons.

 

Zero to a Hundred - Jarrod Guy Randolph | Frank Mastronuzzi | Relationships

 

After graduating, we won the Moot Corp competition but in 2000, the first bubble burst. I then scrambled for a job while everyone was caravaning around Europe with their bonuses that they hadn’t received and their offers that came back when they returned were rescinded. I had a jump on them, and I ended up at a little-known startup in Dallas called Match.com. Online dating, and couldn’t understand it, but I liked the CEO and the new CEO, and I liked the team and my boss. I never had an offer made on the spot and accepted, and that was a great run.

I learned a lot by doing partnership deals and distribution deals with AOL, MSN, and Yahoo. We did a dating TV show by Fremantle that only made one season. It was American Idol for dating. Barry Diller finally got his hands on us. IAC was formed. That’s when I came to LA, and then, after the success of Match, I kept getting requests through Summit Series folks. I started going on the boat for the Summit at SEA, and people kept asking me over and over to help them with their startup, and I kept saying, “No, I have a day job.”

Punch started as a side hustle. We were very selective because I didn’t have time. I wanted to only pick and choose the people that I thought had viability and a chance, and that’s carried through to Punch. Before I knew it, we had so many clients that I couldn’t keep up with it, so I made the jump over to full-time. It’s been quite a wild ride because we have been with some amazing companies.

This is going to give us a lot to discuss. It’s not going to be enough to cover in 45 minutes, but we are going to do our best and this is something we will edit out, were you at Motorola when Ed Breen was there? Ed Breen is one of my very close friend’s fathers. I grew up with his son Matt, and Jeff Rosenthal’s a good buddy of mine.

Alvin’s brother wrote my letter of recommendation for business school. Small world.

The Right Time To Seek Venture Funding

Small world. We are connecting the dots. Let’s get back to it. You have a lot of experience with major companies. Now you work with companies that are startups, but also, I believe, existing companies, and you work with over 150 of them. You’ve helped secure over $850 million in venture funding. Talk to me about when a business should be seeking venture funding and what the criteria are for growth when a venture funding group is looking at investing.

I tell people this all the time. Not every startup and not every organization should go after venture funding. It’s like the advice I got from an MBA. If you are going to go after an MBA, what do you want to accomplish with it afterward, and what do you need that MBA to accomplish? The same thing I say with startups and ventures. The venture is a double-edged sword. Once you have raised a venture, then you have a whole set of going public. You have a whole set of investors that have a microscope that are watching your move. They are on a timeline. They want to exit their funds, and so there’s a whole set of pressure. What I tell startups is to truly not plan their next raise if they are going to do a startup, or venture funding, but you should always plan your next two.

You should think your way through not only your seed investment but your A and B, because if you are going to go, then you need to go all in. With venture, the goalposts keep moving, as you can tell from what’s going on in the marketplace. At the end of the day, I took some advice from my old boss at Match, which was, that if you have good unit economics and financials, if you strip off the title of the company and the financials look good, you’ll never have a hard time raising money. What some founders get lulled into from some of the media is they feel like it’s Oprah on Christmas. You get a car when they walk down Sand Hill Road and that’s not how it works. You have to build a relationship.

You have to convince them that you are moving the ball forward and that they can trust you, and you have to start building those relationships prior to when you need to fundraise. It’s rare that you can knock on someone’s door, get an introduction, and raise money. I always tell people to start building those relationships and showing these investors that they can perform and that you are the right team because raising a venture has gotten more difficult. In the past, it was growing at all costs top line, and we’ll figure out how to make a profit later. and now you can see the likes of Facebook were successful at converting, but Uber is still trying to figure it out.

Start building the right business relationships to show investors that you can perform well and that you are the right team to invest in. Share on X

You have a lot of people still trying to figure out profitability. If you start building something and have a clear plan for profitability and gross margin, and I’m a big focus on gross margin, then going to venture is very clear. Go to them with, “Here’s what we have accomplished with what we were provided, family, friends round, a seed round. Here’s what we were able to accomplish.” Impressive with this round, $5 million. This will get us to this milestone in my opinion,” and always give yourself a little buffer because it never goes according to plan, and show them that you can deliver on those milestones, and manage which is what we spend a lot of our time on. Manage those funds in the time and the runway that you set. If you say 24 months, make sure that money lasts 24 months and don’t overburn. We see that all the time. If you miss your very first milestone coming out of seed or A, it’s going to be hard to convince someone else to give you more money.

Setting The Right Growth Goals While Managing Funds

I want to stay on that topic of convincing someone else to give you more money and separating the growth at all costs from growth efficiently as the market’s looking at. How does a business owner set the right growth goals and, in tandem, still manage the funds that they have in the bank efficiently so they are not overspending?

It’s a tricky balance, and so what I always tell folks, and I see this mistake all the time, is they tap into one stream of revenue and they keep digging until the oil or the well is dry, and then they start looking for 2nd and 3rd paths for revenue. I think you should be testing all the time, different paths of attraction, and so that’s where B2C and B2B came from and all these things, because you don’t want to put your eggs all in one basket, and an investor doesn’t want to see that where you are so heavily invested in one channel. In the early stages, you should be testing different channels and find out where you can get some traction and show that you can get customers from referral partners, from an affiliate program, from ICM.

You do not want to put all your eggs in one basket. Investors do not want to see you are heavily invested in just one channel. Share on X

Show them that you can do those. Those different channels exist because then when you go to them and say, “Give me more gas to put in so I can step on the pedal,” it makes sense. You’ve already shown that you can convert from those channels. I’m always fearful when I see one channel and they keep drilling and drilling until they run out of oil, and then by that time they get panicked and start overspending and throwing spaghetti at the wall to try to find a new source of traffic to keep growing.

Did you ever watch the plate spinner, the guy that spins the plates? You can’t let the first plate stop spinning because it’ll fall. You’ve got to go back and spin that, and so I always use that analogy. I don’t think you should have 7 or 8 plates spinning at first, but you should have at least 4, and you put more money into the 1 that’s delivering right now so that you can keep your trajectory but you should manage your growth. Anyone telling you, “You need 300% or 200% growth,” you need to grow. At the end of the day, if the unit economics in the channel that you are driving traffic is profitable, no one’s going to ever say no to that.

How Businesses Should Handle Partnerships

The plate spinner analogy I think is awesome, and I’m thinking of it in a different way because I have used it in a LinkedIn post that I did and it was talking about following that one plate. Spin the one plate, but what you said is still spin the one plate, what else can you put on that plate? You touched on partnership, distribution, and building relationships, and then you said something key, referrals and affiliate programs. Can any business owner do that? It’s technically not spinning a new plate. It’s getting more, adding more to that plate that’s going to help your business grow because it’s still the same business, you are getting a new stream of income.

It’s a different animal and you have different nurturing requirements. With Match, if we didn’t have those partnerships from MSN and AOL, we would never have become Match because the B2C customer acquisition path, which is why VCs don’t like dating, is too expensive. All the money’s going to Facebook, Google, TikTok, and all those channels.

What made Match blow up was when we integrated and we took some risk because we gave them minimum guarantees and we said, “Put a dating channel on MSN’s portal,” but then we had a partnership management team that was underneath me that said, “Let’s do sweepstakes with our partners in Hollywood and rom-com movies.” We did it with the Dallas Mavs. Win a date to the Dallas Mavs. We did it with Major League Baseball because, in baseball, you can talk while things are happening. It’s slow-paced enough.

We worked with our partners. Valentine’s Day, we created content, we created sweepstakes. We said, “What are the problems you are trying to solve?” Then we helped them accomplish that because then we would get more traffic out of that, and it was a win-win. To me, it’s the 80-20 rule too, even in this business for Punch. 20% of our partnerships give us 80% of the referrals. You bet your ass I’m going to spend time taking that 20% to dinner, calling, checking on them, asking what they can do to help if they want me to speak whatever it is. It’s a good precursor to building relationships with VCs too. If you start nurturing those relationships, they will start paying off in spades.

I saw one of the merchants that I worked with for many years owned about 25 pizza shops. Big company. They were doing well, but their biggest growth wasn’t through the physical pizza shops, and this is like a B2C, or it would be a B2B partnership, that they did. That is important because our audience of entrepreneurs and business owners is always looking for ways to level up their game.

What this pizza company did is they did partnerships with party planners, schools, construction companies, and little leagues within the regions that they were in, and they freaking murdered the game, and they were selling their pizzas at volume at a discount but it’s like the construction company, they had their guys doing Pizza Fridays, and for the workers, they would buy pizza for them.

Their revenue and their margin grew substantially because they were also booking those sales ahead of time because they knew that they had a 1, 2, and 3-month plan where they knew for the little league, every Saturday they were selling pizzas to them throughout that summer. The partnerships, what you said, a lot of people think of them on a big scale even on a smaller scale. Now, this was a company that was doing almost $60 million a year. They weren’t a small company, but if you think about it, not only on the big scale, but on the small scale, there are ways to form partnerships for any type of business that you have, and those relationships can take you to the next level.

In that instance, that’s a brilliant idea because I think about it, what happens to the individual construction worker who eats that pizza? Then all of a sudden, when he goes home to his family, who’s he going to recommend? This pizza’s good and it’s not expensive. Two things. For Match, it was critical because we were still in the early days. People thought online dating was risky. We needed the validation by being integrated into MSN AOL and all those other companies. It gave a second form of validation that this is safe, and so it helped us in a lot of ways on the PR side.

That’s one, but the recurring revenue is king in any business, and so what you mentioned about the pizza place and Match, getting a B2C is tough because you have to keep paying to get that new customer. B2B, that construction company, the little league, they kept buying. You didn’t have to resell them. Your customer acquisition costs over time on that customer go down dramatically because they keep buying, if you look at volume, and for us, it was critical.

I like to see that when I work with startups because even that pizza guy is thinking outside the box. After all, most pizza companies aren’t, no pun intended, but it was, “Hey, ” and I will take a recurring revenue business any day. Our financials, we break it out all the time. What’s one-time revenue, and what’s recurring? It’s because investors want to see recurring revenue, and so how you get recurring revenue in any business is important. That’s why people love B2B SaaS because it’s hard. That customer usually stays. The life or the LTV of that customer is longer. When you have high churn, it’s a tough business because you are on a hamster wheel. You’ve got to keep selling.

Securing A Recurring Revenue In Business

From a venture standpoint, when you are looking at that business that has that recurring revenue, how does that increase their market value or their multiple versus a company that’s one-off sales? They might still be VC, they might still be growing, but they are having to do one sale at a time.

It’s infinitely more valuable if they acquire recurring revenue. You don’t have to keep fueling the flames. The flames are there and you have to nurture the relationship. Then you need someone that’s going to reach out to those partners and say, “We are doing a promotion,” “Here’s a holiday gift for your company. Thanks for being such a good customer,” and then it turns into a CRM type of project because staying top of mind is important so that when they do it.

We at Match went as far as coming up with ideas to help them stimulate their clients too, and giving them the tools. When you build a program, give them the marketing materials that they can use. Give them the content. For Match we did dating that was related to Valentine’s Day, then Halloween, and “Don’t be lonely.” “Don’t go to Thanksgiving dinner by yourself with the family this year.”

We would use ideas to help our partners drive more traffic, and then we would show them that it was working. They were deriving more revenue. A recurring revenue referral fee as it becomes an annuity. They get addicted to it too all of a sudden, it’s like, “Why not?” It’s a smart way. It takes energy and it takes consistent reaching out. It’s like anyone.

You can’t reach out a year later and be like, “How’s it going? Where have you been for a year?” If you are going to do it, you have to commit to staying on top of it, and we do that at Punch where I check in with our partners once a quarter automatically through CRM, and I’m always like, “Do you want to jump on a call?” If I’m going to that city, I plan a night at one bar or restaurant and say, “Everyone stop by if you can.” Staying top of mind is important.

Creative Ways To Build Key Relationships

Talk to me about some other creative ways. I love the idea of your key partners when you are traveling, especially for you because you travel a lot. Being in a city and that. You set up shop in a bar one night and you invite people to come stop by and have a drink because they also start to network with each other as well. What are some other creative ways that business owners can create that connectivity, and stay in front of their key relationships? As you and I know, these types of things and activities build your business, and it sometimes might seem like it’s a lot of extra work for entrepreneurs to get out there and do that. Those are the things that you can do, which can take your business to the next level. Are there other ways that you would suggest business owners look at doing relationship building as well?

I like to cross-pollinate, not only existing clients but prospects because the best way to sell a prospect is to have them talk to an existing customer that’s happy. When we do roundtable dinners or events, I never end up having to sell the prospects because they see how happy the other customers are, and it’s human nature. If they are like, “Punch is great, and Frank is great,” I don’t need to keep my own horn. They are doing it for me, and so I like to cross-pollinate between existing and potential because then it also, as you said, putting them in the same room, they start seeing who you are working with. They realize that there’s a value-added there. They might have met 1 or 2 people that they are going to stay in touch with now, and you get that positive goodwill by doing it. It’s a pay-it-forward type of thing that in the long run pays off in your career.

One of my friends here in LA, Keith Ferrazzi who’s a famous author will say this all the time, “If you are building those relationships over time and they like you and they like doing business, then it’s easy for them and you to continue making that relationship become positive ROI over time.” Once you have someone in your corner, they could also be a referral if someone’s questioning.

 

Zero to a Hundred - Jarrod Guy Randolph | Frank Mastronuzzi | Relationships

 

He would do that with, or in a Huffington in the early days. He wrote the book Never Eat Alone, and they would anchor their dinners with someone, one of their clients, and then they’d say, “So-and-so is coming, you should come,” and all of a sudden, they are like, “I want to go,” because whoever’s going to be there. Ariana Grande, I will throw that up. Not that level, but it was always someone in the business community or a hot startup, and people of other hot startups. Here’s the big misnomer. Not all founders know each other.

When you are like, “The founder of Vapi AI, one of our hot startups.” If I were to say Vapi was coming and the founders were coming, I’d be able to pull in a ton of people because they are all over the press right now. That’s what you do. You want to be surrounded by winners. Talk about sports. You want to surround yourself with winners so that you raise your game and your level. Same thing. It takes time to build that. By building those relationships, following up, and building longstanding relationships. Call them on their birthday. Do those things that people aren’t doing. It pays off in the long run.

I love the idea of the comment that you made about building human relationships because that human capital, that relationship capital is tantamount to success, and it’s something I have been doing for years. You and I have had this discussion, which we’ll follow up about how magnificent your dinner was. Before I lose my thought, Never Eat Alone. Did Arianna Huffington write that?

No. Keith Ferrazzi did.

Keith Ferrazzi. Writing that down, and for the audience, Keith Ferrazzi, Never Eat Alone. I’m all about the building of relationships. Another idea to throw in there is if you are a business owner, I now understand what one of my other clients, which was, they own eight lumber yards, would do dinners, but they would do dinners with potential partners in the communities in which they had the lumber yards.

Whether it was the heads of construction companies. It was the heads of distributors and suppliers. It might be like cigars and steaks, something like that, or like a scotch night, but they would take their network and introduce each other. It might not have necessarily been for a client, but it could have been for that potential partner or distributor.

This is a little bit different than the conversations we typically have, but the reason we are having this conversation is that in 2025, we have to think about ways to grow our business. The way you grow your business is by buying favors with your network of influencers. They drive more people, drive more traffic, which drives more revenue. Get creative about the way in which you connect with your customers and your community.

Those that will produce recurring, because with COVID and everything, we have gotten too far into it that everything’s transactional, and no one’s taken the time. That’s why people say, write a thank you card physically no, because no one’s doing that anymore. It’s the same thing in building relationships. I never drive anywhere now, especially with LA being trafficked, where I’m not calling a partner or someone saying, “I’m checking in.” Even if I don’t talk to them, by leave a voicemail saying, “I was thinking of you. I wanted to check-in. Let’s catch up.” That’s it. The fact that I merely thought of them, and in this day and age where I’m consistently checking in with people.

I cheat. I use a CRM that’s like, “You haven’t talked so-and-so with Jarrod in two months. Time to ping.” We are human, but it’s important. It is. It’s the media’s fault. TechCrunch makes it seem like you can run down Sandhill Road and be like, “Nice to meet you. Here’s your check.” That doesn’t happen. You have to build a relationship and show them that you can deliver and show them that you have surrounded yourself with a good team. That’s what they talk about a team and that’s how you do that. You build that relationship over time.

You have to build a relationship with investors and show them that you can deliver and are surrounded by a good team. Share on X

I always tell them, “If you need money from them in the next six months, you waited too long.” You should have started building. I like recommending, “Reach out and say, ‘I want to let you know what we are up to.’” We are not raising money right now. I want to get your thoughts. The adage is true. If you ask for money, you get advice, and if you ask for advice, you get money because you are coming in under the pretense of you want them to take a look at stuff. They start asking questions.

I always tell people that I have had founders too. Don’t make the mistake of I got to get through my whole deck. I’m going to make them read every slide. The more they are engaged in asking questions the more they are interested and the more they lead the conversation then. Don’t interrupt because then they are going to start thinking. You want them to start problem-solving for you. Have you thought about this? Have you talked to so-and-so? I tried to get in there. I don’t know anyone at Motorola. Do you know someone who can help me?

9 out of 10, when you put it that specific, they are like, “I know so-and-so.” One second. Boom. Done. Now you are in because you got in by someone very important. I always say this too, and all my startups, “Shoot for the stars on the advisor board because they were once a founder too, and the fact that you are reaching out and if you can convince them, that’s when you get the moment.” They are like, “I’m not ready for it.” I’m like, “That’s when you reach out, but do your homework. Find out something that, like you and I keep finding overlapping concentric circles.”

That’s what they need to do, and when I get an email on LinkedIn that’s like, “I saw that you went to the University of Texas and you worked at Match and it shows me that they did some homework, I am 99% more likely to respond to them, even if it’s a nice polite no, than if it was some AI-generated, which you can tell. My thing is, don’t be lazy.

You are better off reaching out to ten people with thoughtful questions and, “I want your specific help on how to sustain a subscription business over time. How did you do that? Those are things that are going to get my attention and show me that they did some homework, because it’s unfortunate, but again, the world is too transactional at this point. I don’t have time for transactional folks because I like to do business with folks that then in turn, I can spend money with them too.

All of our partners will tell you, I don’t like business to one, we send a lot of referrals, but I will tell you that if a partner doesn’t even attempt to send a referral back or co-host a dinner with us or do a webinar with us. If there’s not a two-way street, those relationships end fast. I have learned that if you have a two-way street and they are truly a partner, then that’s what’s built our business, and we haven’t spent a lot of marketing budget in building Punch. I have spent a lot of time building relationships, which by the way, whether they bring me business or not, I’m making great relationships regardless.

I’m still rich in both senses of the word, meaning I’m rich in partnerships and relationships, but I’m also building and scouting the phone with bankers who have now become personal friends and we are going on holiday together. My point is, that that’s what the younger founders need to understand because they get laser-focused on, “I need $100,000 in MRR to raise a $10 million series A,” and that’s all they stay focused on. 1) You are not enjoying the journey, and 2) People see that, and no one wants to do business with people like that. They want it to be, “As an investor, I want to go along for the ride. I want to enjoy it.”

The Right Way To Build Your Own Board

That’s very good advice for anyone who is in business, whether you are a startup or existing because people get stuck in their lane and they are doing the technical tasks that they do on a daily basis, and they forget what the true idea behind being an entrepreneur is, which is connecting the dots. Audience, this is not the conversation that I was expecting to have, but it is an incredibly important conversation. It’s the only time we have dived into the importance of relationships and how to genuinely build them, but how you monetize them for your business. You said something important, and it’s something that has propelled my business and my career, and that’s the board.

 

Zero to a Hundred - Jarrod Guy Randolph | Frank Mastronuzzi | Relationships

 

I don’t care whether you are that pizza shop with the 25 locations the lumber yard, or a business like mine or yours. I have an advisory board, of seven key people. One was the chief of staff for a senator. There was one who was the chief creative officer for one of the largest real estate and product companies in the world. There’s one that is a major figure in AI.

The reason I put that board together is because I get value out of learning from them. They have an incredible network, which helps me build my business. They have an equity share within the company, so they are vested in giving me their time and access to resources, and it’s an easier way through the door and to build trust immediately with key relationships. What advice would you give a business owner, whether they are a startup business owner or an existing business owner on how to build out a board that can help you grow your business?

I was going to ask you a question back, which was, how scared were you to ask each one of those to be an advisor?

There was some trepidation there. I had my come-to-Jesus moment. I’m like, “All they would do is say no,” but I will tell you what’s so funny. I had relationships with all of them.

It wasn’t at this level. You had to build it and show them that you wanted it, because every advisor, even any mentor wants to help, but they want to know that the time they are going to spend is well spent. That’s what you have to demonstrate to answer your question. I tell my founders all the time, “If you are not afraid to ask them to be an advisor, then you are not shooting high enough. You should be afraid of them saying no, and the worst thing they can do is say no. All of us have been in their shoes. When someone reaches out and says, “I want your advice on this, can you help me?”

Sure. I’m going to see it again. She’s famous for doing the relationship webinars at Summit. I am blanking on her name, Esther Perel, and so she would meet me. She’s like, “You wouldn’t show up to a board meeting unprepared,” but yet this was because founders were losing their relationships, and she’d say, “You show up to date night with your girlfriend completely unprepared. Why would you think that relationship’s going to last because you show up and you are not present?” It’s the same thing.

Come prepared in your relationships, the same with these advisors. Come to them and find out exactly. I want you to share how you get what you got. Everyone wants to tell their story. Everyone likes to talk about themselves, but they want to make sure that I’m going to spend the time nurturing that relationship, or if that mentee is going to turn into something.

That’s also the true fruitfulness of what I get when I mentor. I had a 500 startup company that I had beaten up on over time and refined their model, and then last, this last December 2024, it was the 500 startup Christmas party, and there was this founder who said he had closed a huge round and everything I had pushed him towards like, “Have it come full circle,” and for him to thank me and say, “If it wasn’t for you, we wouldn’t have gone on this path and the tough love.”

I was happy about that. He was happy about that, and we have stayed friends. A lot of our clients that go on to success stay friends because no one forgets that when you are in the trenches, you were there for them when they were doing that. I always tell people, to spend the time building your advisory board. It’s important because it’s going to show the investors that you could build relationships with the board members, and that’s going to be critical.

How Founders Can Become A True CEO

One of the things that you mentioned about the question you posed, how nervous were you to ask them. A book I read called Mindset by Carol Dweck, and I think Bezos did a quote for her on the front of the book if I remember correctly. She talks about the concept of imposter syndrome. Imposter syndrome is something to be embraced because that means you are always pushing yourself beyond your limit.

Some people who are the most successful suffer from what they call imposter syndrome, but it’s not something you should look at as a negative thing. It’s something that you look at when you are pushing your envelope to advance in your career continually, and that type of growth leads to massive success. When you go outside your comfort zone to make that ask of someone, you’d be like, “They would never advise me,” or, “They would never mentor me.”

Here’s one thing that I have found, some of the most successful people out there have said this to me. Very few people come to them and ask them for their insights and guidance. That’s one thing that blew my mind because people are intimidated. Put that list of people, whether they are in your community, they are in your network, whomever you think you can add value to, and they can add value to what you are doing and have a conversation with them.

When people show me why they are reaching out to me and have done their homework. You’ve lived this, you did this, you worked with this. That to me shows me that they spent some time. It’s important. This lesson we are talking about does spill over to partnerships and does build work at the building, because at some point I tell my founders, at the early stage, you get hell-bent on focusing on product sales, and fundraising.

At some point, you hire all the best you can like us outside of that, you hire the best accountants, customer acquisition, or lawyers until you can bring them in-house. At some point, the role has to switch. If you are going to switch from founder to being a successful founder of a fast startup, you have to switch to becoming an ambassador. This means you still have to recruit the best talent in-house, and then you need to make sure that you are giving them what they need to be successful. The CMO, the CTO.

At some point, you are no longer doing the work, you are guiding, encouraging, and helping, removing roadblocks for them, and that’s a successful founder who transitions from doing everything to becoming a true CEO. A lot of times those founders can’t make that. It doesn’t have to be a tech startup, but any company, at some point, you have to build trust with the people, and I saw this on LinkedIn. It’s going around right now. It’s like, “Having a job is not satisfying enough. It’s being seen and being cared for at that job. That makes the job fruitful.

Having a job is not satisfying enough. It is also about being seen and cared for in that job. Share on X

The same thing. They want to know that their opinion and their input are there and that you are nurturing them. That’s what their role has to be, and they have to switch, and it’s hard to make that switch, and not everyone is good at that. At the end of the day, you have to, at some point, become that ambassador where you are like, “How can I help you get accomplished what you need to, which is 2X revenue this next year?” What can we do? What do you need, check in from time to time on a regular basis and give them milestones.

Key Hires In Building A Successful Company

We had a great guest, Dr. Kent Wessinger, and we had a conversation. He’s the foremost authority in Millennial and Gen Z workforce mentality, and retention. It was a cool conversation because he talked about how much they care, and they do want their voice heard. They want to be held accountable, but they also want to have leaders around them who are willing to be held accountable as well, and that should be the full vertical of the business.

When you are running the business that you are seeing growth in. I want to stay on the concept around team and culture. Once you get beyond building a successful company, or whatever it may be as a CEO, who are some of the key hires that you should bring in that can help take your business to the next level?

Hands down is operations and COO or some form of operations because what happens over time I see is that if there’s no structure just like you talk to kids that were in the system of not having parents. What they will say is that all the homes that they were in, that they had structure, felt like they were loved more because there was structure and a framework for them to succeed. They knew what was good and what was bad and what would make them successful and what would not make them successful, and the same I see with a lot of startups. They don’t put in operating procedures. I always believe that people want to do the right thing. There’s always the exception, but for the most part, most people want to do the right thing, but they have to know what that is.

If you don’t tell them what the right thing is to do in this situation, then when they do something wrong, how can you hold them accountable? What you need to do is figure out what the process is and what’s successful, and then what we tend to do is always go after when things go wrong. Let’s put a procedure and let’s communicate to the staff that this is how. A good example of the early days is always travel and expense management and credit cards. Fly first class. There’s now technology that will help you manage that, but you should document it so that also people know what they are being held accountable for.

Ops is important. It doesn’t have to be a COO per se. I think it’s also the HR person. There’s a little bit of overlap because someone needs to write the procedure and figure out the process the other person needs to document and communicate it to the employees in a positive way. Positive reinforcement works, and people tend to go to negative reinforcement right away, but positive reinforcement works well. When you launch something with positive reinforcement like, “If you turn in all twelve expense statements on time this year will be put into a raffle for a trip.” Positive reinforcement, instead of, “If you don’t turn in your expense statement, we are going to write you up,” but if you have it as positive reinforcement, that’s where people go wrong early on because they get frustrated and are stretched thin.

I always say, “Find a good ops person.” It doesn’t have to be a COO, but it has to be someone with attention to detail. Anytime you’re channeling into a different territory, we always say, “What’s the process? Who do they reach out to? What’s the form? Who approves it? Is it Slack?” You document it so every new person that comes in next gets the handbook that is continuously built on. You create different categories, but you know what they are going to be upfront, and you start building them.

The Dangers Of Hiring Too Fast

Unfortunately, we are almost at the end of our session, which is driving me nuts because I have six more questions I want to ask you. That means you do have to come back. This might be like a regular quarterly thing so you keep giving sage advice and wisdom. One last question before we get into the rapid-fire section. You’ve worked with some other very high-profile startups like Honey and Boulevard. What are some of the lessons you have taken away from helping build those companies that any business owner, no matter where they are in their business can use to create more growth?

In those instances, two things always held. You say seven habits of highly effective people. I started building my seven habits of being highly effective entrepreneurs. There are a few that I keep seeing people make mistakes on. One is when they abdicate the responsibility for finances. I get that most founders don’t like accounting and finance. It’s not their strength, but you got to know your business, and if you don’t know your levers and you don’t know your financials, then you’re not flying the plane, you’re letting someone else. That’s one.

Two, the adage of hire slowly, fire fast. I see this all the time. People end up hiring their friends, their classmates, whatever it is, and then it doesn’t work out because they are a great drinking buddy or they are a great whatever/player, whatever it is but it doesn’t always translate. My thing is to hire people who are qualified, and who want to be there, and not because you’ve known them and they are good people because it doesn’t always translate.

Hiring tends to fall at the end of the day when I get everything else done, then I will start looking at it. The founders of Honey and Boulevard at the beginning spent a lot of time interviewing and hiring every employee in the early days. One of the biggest mistakes most companies make is they hire too fast, and then there are no procedures. People are wasting time. They don’t know what they need to be doing.

If you are hiring as you need people because the other folks are too strapped and can’t get to everything, and you are giving them clear, here’s your job responsibilities, here’s what we need daily, weekly, monthly and you are hiring as needed because clients are being added instead of, “We raised $10 million. Let’s hire a bunch of people.” I see that all the time. No, what are they doing? Why do you need that? Hire them after you bring in the business.

Those top two for me, Honey and Boulevard both acted like they always had $5 in the bank. With every financial decision, they didn’t act like they had millions of dollars, which they did. They acted like they had thousands, and so they made very strategic, smart decisions every time. When you hear, “We have the money, what’s the big deal?” No, because we may not always have it, and the people who act that way are struggling right now.

Everyone says it, but I have seen it too many times, and 9 times out of 10, the HR problems that exist in early startups are always, “It was my buddy in the fraternity.” I have seen it too many times. It’s always like, “They were my best friend growing up.” Now, they are suing you, so good luck. You’ll hire for expertise, and I always like to hire based on want and drive. I will always take someone who is lower level, who shows initiative, drive, and want, versus someone who’s done it and is bored.

Answering Rapid-Fire Questions And Closing Words

Are you ready for the rapid-fire section?

Yes.

Give me quick answers on this. Coffee or tea?

Coffee.

Is there a phrase that you think about often in business?

Don’t put off until tomorrow what something you can do today.

If you had the chance to have dinner with someone tonight, dead or alive, who would it be and why?

I would say Leah Akoka.

Give me three money-saving techniques that any business owner out there can employ in 2025.

I would say one is constantly reevaluating every spend every month. Ask yourself, “Do we need this?” I see all the time when I challenge them, and it’s like, “Do we need five seats for this? Can you use one login?” I always constantly say, look at every expense and ask yourself, “Do we need this? Can we get by without it?”

Two, like you were saying finance techniques. I would always constantly be managing the budgeting. People don’t budget and manage to budget. I don’t dig into variance versus budget. QuickBooks allows for budgeting. Most people who use QuickBooks don’t ever touch budgeting. Even if you set last year’s numbers as a budget and looked at it because if you wait too late, you have to constantly, we always use the analogy of expense management and budget management. The Titanic tried to turn so fast once they realized they were so close to the iceberg that there was no chance in hell for them to turn so they hit the iceberg.

If they were constantly moving right then when they realized the iceberg was there, they wouldn’t have had to move much. What I tell people is to constantly review your financials on a regular basis. Don’t wait quarterly, do it monthly and make small pivots and adjustments because if you wait until the quarter or year-end, it’s too late. It’s already too late. The boat’s taking on water.

The third is to always act like you only have $5 in the bank. If you are managing your finances as if you don’t know where you are going to get your next million. Those frugal, thrifty, savvy founders always succeed because they are not caught without money. I will use a perfect analysis like how the hell did Bench shut their doors? They are an accounting firm. How did they know that last year? That’s a good example of how you shut your doors with no notice to your clients. You had to know and you had to be communicating. That’s a good example of not running your business that way.

Frugal, thrifty, and savvy founders always succeed. They are not caught without money. Share on X

That’s going to be the name of your book Act Like You Have $5 in the Bank. That sounds like a fun one. Last question, but not least. What is the one obstacle that you had to overcome personally to build the success that you have built?

Not give a shit what everyone else thought. Constantly, it goes back to the imposter syndrome. I was always worried about, “What are they thinking? Did I say the wrong thing?” I always second-guessed myself, and then I realized, that if you deliver full circle if you are a good person, you are building relationships. I admit when I make mistakes, I’m human. Everyone can empathize.

Once I started realizing and stopped apologizing for who I was, but did the best job I could, that’s when my career took off because I was always worried about, “Do I have an Ivy League education?” I don’t have an Ivy League education. How am I in this room with all these other people? Again, the imposter syndrome creeps in, but if you do good work, no one cares at the end of the day.

People remember how you make them feel. The same thing in business. People remember how you make them feel and how you performed, and if you performed, because I forget some of my clients, and they come back. I ran into another one, super successful, and he was like, “You taught me so many things that I still preach to my team to this day,” and I was like, “You forget.” Those are the things. That’s what I would say.

Please tell everyone where they can connect with you if they would like to do so.

In my Email. You could reach out to me there or on Instagram and Twitter, the same thing, or you can come to our website and contact us.  Those are the easiest ways, and I’m active on LinkedIn, so reach out to me there.

Frank Mastronuzzi, thank you so much for joining us on the show.

Thanks, Jarrod. Have a good one. Bye.

 

Important Links

 

About Frank Mastronuzzi

Zero to a Hundred - Jarrod Guy Randolph | Frank Mastronuzzi | RelationshipsFrank has extensive experience as a CFO serving private companies in the software, e-commerce, and medical device industries. During Frank’s career, he has served as interim CFO to over 150 startups who have raised over $850MM in venture funding, including companies like Honey, Boulevard, Sanas.ai, WaveXR, and many other startups.

Frank’s experience includes managing the day-to-day accounting functions, financial analysis, HR, treasury, legal, and risk management. Frank has completed over 25 mergers and acquisitions as well as extensive experience in audits, planning and installing accounting controls, and negotiating contracts and business development deals.

Frank is Founding Partner and CFO of Punch Financial LLC, a specialized accounting and bookkeeping firm to venture-backed startups. Frank was also responsible for the company’s financial, accounting, and administrative functions. Before Punch Financial, Frank worked at Deloitte, Motorola, Match.com (an IAC Corporation), MyLife.com, AmericanGreetings.com, and Curbstand.

Frank is also Managing Partner & Founder of PunchUp Ventures. An early-stage venture firm investing in tech startups that are clients of Punch Financial. By managing the accounting for our portcos, PunchUp Ventures conducts on-going due diligence with our investments.

Frank has a Master’s Degree in Business Administration from the University of Texas at Austin. Frank obtained his Bachelor of Science in Accountancy from the University of Illinois at Urbana. When Frank is not helping startups grow, he is spending time traveling outside of LA with his husband, Javier, and his two soft-coated Wheaten Terriers, Luca & Lola.