Bobby Ocampo: One Job Away From Finding the Right Career Path

A Silicon Valley native and Founder of Blueprint Equity, Bobby Ocampo always knew he was destined for the tech space. He was raised by two intrepid tech entrepreneurs who inspired his passion for innovation, starting at a young age. 

Like so many of us, Bobby completed undergrad without a clear vision of where his career path would lead. If you’re feeling a similar sense of uncertainty, check out our recent article on Redefining Professional Networking. 

In Bobby’s case, finance felt like a good fit at the time, but not 100% right. So, he jumped headfirst into the financial sector, where he spent the first two years of his “young professional” stage of life. 

Despite all its perks, the finance world felt empty and transactional, and Bobby knew it wasn’t where he belonged.

How Bobby Ocampo Let Go of the Comfort of Familiarity to Embrace the Unknown

In my recent Standing Out article, I spoke about my inner battle when I had to face down the decision between a comfortable, secure, and elite job in sports marketing, or listening to my gut. If you’ve read my story, you know I chose the uncertain path that I knew was right for me, and you’ve seen how that visceral feeling was the right one to trust. 

Hearing Bobby’s story, especially how he had to grapple with a similar dilemma between security and standing out, really hit home for me. After he realized this wasn’t the life he wanted, Bobby found the courage to re-route, stand out, and fearlessly pursue an unknown trajectory. 

Carving out his own niche at the intersection between finance and technology has paid off better than he could have imagined.  It takes a lot of resilience to take a huge risk and bet on yourself, but Bobby is a living testament to the value of this specific type of courage.

Here is Bobby’s advice for young professionals who are on the job market right now:

“For any student or professional, I would think about clever ways to conduct outreach. The days of dropping a resume in and waiting for a response doesn’t work. What I did was, when I would go and talk to these firms, I would create a pitchbook of companies that I think they should invest in and why. They were probably all bad ideas, but they got their attention in a way no one else did. We receive resumes at Blueprint all the time from people who are all smart and hardworking, but you’re not going to stand out in a crowd with that alone. Frankly, what we look for are people with that unique ability to catch our attention.”

As a business leader, he draws on the insight he gained during his tenure as Partner at Steve Case’s investment firm, Revolution. For nearly a decade, Bobby called Washington, DC home. 

Now, as a disruptive force in the FinTech world, Bobby jokingly refers to himself as a “recovering I-banker. His San Diego-based company, Blueprint Equity, is a tech-focused growth equity firm “focused on investing in and building market-leading enterprise businesses.”  

My Top 5 Takeaways from Bobby Ocampo

1. Take a Different Approach to Job Applications:: Dumping a generic resume into every job opening probably won’t get you an interview. Go above and beyond. Follow up and leave a unique impression. If you want to be memorable, make yourself stand out. 

2. Always Question those Nagging Feelings of Doubt You Have Inside:  Deep down, Bobby realized he wasn’t happy in finance, even though everything looked perfect on the outside. He got honest with himself and pushed out of his comfort zone to make a change

3. Learn How to Make the Right Changes From People Who Successfully Have: When you decide you want to start making a change, do it with someone who has before. Bobby’s transition from finance to working with Revolution gave him instant credibility. 

4. “You Can’t Connect the Dots Looking Forward; You Can Only Connect them Looking Backward” – Steve Jobs: When he started his career,  you told Bobby he’d have his own investment equity firm within 10 years, he probably wouldn’t have believed you. His life took a lot of twists and turns, but the aggregate value of all his prior experiences led him to where he is today.

5. Treat Others the Right Way: Bobby has such a genuine caring for human kind, and it always shines through when he’s being interviewed. This unique trait is always so much bigger than the job at hand. It’s the people around you who make any vocation special. 

Bobby has departed some seriously valuable insight and perspective to me in the time we’ve known each other. He is so many things I strive to emulate:

• Thoughtful
• Intentional
• Driven
• Well-spoken 

He’s one of the most interesting people I’ve ever talked to, and this episode is really fascinating. I’m so excited for you to watch this episode, and I hope you benefit from his words of wisdom as much as I have! 

Follow along on the YouTube link up top, or listen on Spotify or Apple Podcasts. A transcript is available below if you prefer reading to listening!

Transcript

BRYAN WISH: Welcome to the latest episode of the One Away Show, featuring Blueprint Equity Founder Bobby Ocampo Ocampo. Tell us, what has been your One Away moment?

BOBBY OCAMPO: I went to Middlebury for undergrad, a small liberal arts school in Vermont. I grew up in Silicon Valley and my parents were entrepreneurs and worked with technology. I knew I wanted to do something along those lines but I wasn’t sure yet. When I was an undergrad, the resources out there today aren’t what they were when I was still in school. You try to figure your way out and figure a way around whatever you want to do in your career. I knew I wanted to be in tech but I didn’t know if I wanted to start my own company or if I wanted to join a startup. A lot of my friends in Middlebury were all Econ majors and were applying to finance jobs; mostly IBanking jobs. I said, “Perhaps I can do that too knowing nothing about finance, but compared to physics, it was significantly easier.” That was it.

I applied and got a few offers. I picked the bank I worked at based on the one that let me pick my group and my location. I knew I wanted to work in tech. I knew I wanted to be back in the Bay Area. That was really it. It wasn’t super planned out like a lot of students are today. If you look at a lot of our analysts and associates here, they’ve all had this planned, mapped out in their brain many, many years before I even thought about it. Our folks here, they know exactly what they want to do when they get into college. They’re heads and shoulders way above where I was when I was their age. 

BRYAN WISH: In our earlier conversations, you mentioned you maybe would have done things a little bit differently looking back. How would you approach that decision after school to maybe do it differently than how you did it and why would you have done it differently?

BOBBY OCAMPO: I’m happy I did the banking tour like everyone does. If I had to do it all over again, I probably wouldn’t have done it. It was mostly because it’s such a difficult position to do for two years out of school. You go from having a decent work-life balance in college to having no work-life balance after school. Couple that with – I was a banker from 2007 to 2009 and that was basically the worst time to be a banker. Not only are you working a million hours a week, you’re working on transactions that are likely not going to close and people are just throwing ideas on the wall. Thirdly, a lot of your friends are getting laid off. Your work load is increasing and you’re likely not getting compensated like people were in 2005-to now. 

It was a mix of all those things. I probably would have liked it a little bit better if the economy was doing better. I don’t know if I would have done anything different. I’m happy I did it. I met a lot of great people. It got me here, but it was definitely a dark spot in my life. 

BRYAN WISH: There’s a quote that says, “In every crisis, there’s an opportunity I really like.” What was that silver lining for you and what did it push you to do to find the path that was better suited for you long-term?

BOBBY OCAMPO: Fortunately, the analysts are analysts for two years. It’s very finite. That was always a silver lining where the first year, I was enamored with the job because I was learning something new every day. It was really exciting. It was fast-paced, frenetic. You’re always doing something new and you’re still learning. After a year, you basically know everything you need to know to do the job well. 

For the next year, it’s really all about doing the work efficiently, mentoring the new folks who join and interviewing for your next job because banks don’t expect to stay there beyond two years. If you do stay there beyond two years, either love doing it or more than likely, you didn’t get a side job. 

That was really silver lining that as an ibanker, the transactions I was working on were really all about selling privately held companies. You’re on the south side. We’d be approaching a lot of the investors, gross equity firms, and private equity firms to buy the clients that we’d be engaging with. 

I knew I liked the business, but I wanted to be on the other side of it where we’re not trying to market and transact. It’s all about transacting on the other side, but also building and growing.

That was it. I knew the skillset I’d be learning would be able to apply to being an investor. Surely not everything that I learned, but that was it. You’re here in a job. You’re here to learn and work really hard, but the silver lining is that you get to hopefully be an investor buying the companies instead of representing them to be sold. 

BRYAN WISH: What was next?

BOBBY OCAMPO: Within 6-9 months of starting my tour as an I-banker, you get a lot of recruiters and headhunters who are trying to place you into the jobs that their shops are representing. 

After my first year, I was getting hit up all the time like all my other colleagues were. They’re largely private equity funds, growth equity funds, not a lot of venture funds because venture funds   hire ad hoc. There’s not a structured process like there would be for a growth equity firm or for a private equity firm. With venture, it’s a lot more about whether we hire when we need him or her. It’s cyclical; the hiring comes and goes when they’re able to raise a new funds. There’s no structure. 

I was interviewing at a bunch of places. I got a few offers at private equity firms, growth equity firms, but there’s one firm in Washington D.C. that I just cold emailed. I liked their strategy. I liked what they were doing. It was probably the only true venture fund where they had a position. It was a firm called Grotech Ventures in D.C. 

At the time, I had lived in San Francisco. I’m from the Bay area. This firm across the country was looking to make a hire, I interviewed, went through the process, and that was it. 

BRYAN WISH: Something that’s a common theme here is taking that risk to stand out and cold email, which is what you were saying. Having the nerve to put yourself out there and talk about who you are and what you want to do can lead to some really great things and fortuitous moments. 

What advice would you give about reaching out to other people to help you get on the path you’re meant to be on? How did you go about that process?

BOBBY OCAMPO: We have a heavy outbound sourcing function here. We’re not a venture fund; meaning, we don’t invest in venture style companies. Yes, we’d love all other companies to be trillion-dollar outcomes, but in that case, you’re assuming a lot of downside. A lot of times, VCs are investing in ideas. A lot of those ideas don’t become a business and those businesses don’t become good businesses. You really have to have stars aligned in a bowl market for a company to really fork out in venture land. 

How we approach it at Blueprint is that we’re not as interested in those assets because there’s just too much downside. There’s too many things out of our control that can go wrong. We try to partner with bootstrapped entrepreneurs who have proven they’ve got a business to a certain scale.  Not big yet, but to a certain scale. We come in and really help them with three things: build sales and marketing functions and their engine from scratch, recruiting around those functions, and corporate development. 

We help them source and execute transactions and tuck in acquisitions on their behalf. It’s a lot more of a proactive approach than a reactive approach. No other companies we’ve talked to have raise institutional funding. They don’t have prettied up decks. They’re just concerned about, “How do I get more business and how do I pay payroll?” Those are the types of opportunities that entrepreneurs and we will really jive with. 

To backtrack to your question about putting yourself out there. When I was reaching out to venture firms, I cold emailed probably over 100 of them. I had a spreadsheet and I got around a 30-35% response rate of which probably 60-70% said, “Thanks, but we’re not really looking to hire.” Probably four or five of them turned into them looking to hire but not sure when. Two or three of them said, “We’re actually looking to hire right now.” It was all a numbers game. 

This is for any student or professional. I would think about clever ways to conduct outreach. The days of dropping a resume in and waiting for a response doesn’t work. What I did was, when I would go and talk to these firms, I would create a pitchbook of companies that I think they should invest in and why. They were probably all bad ideas, but they got their attention and no one else did it. 

When we get resumes in at Blueprint all the time, people are all smart and hardworking, but you’re not going to stand out in a crowd. Frankly, what we look for are people with that unique ability to catch our attention and some chip on their shoulder, some internal motor that gets them going. We have very much a self-starter culture here. You either thrive on it or you fail, and it doesn’t work.

For anyone looking to get into this industry, the best way to do that is to be able to deliver a message that’s short and concise and deliver immediate value to the reader. For example, “You know what? Bryan Wish just emailed me. This is great. He said something that no one else ever said to me or he said he’s actually got an interesting company that we should be looking at and it meets our parameters for X, Y, and Z reasons. No other candidate did that. I don’t care where you went to school. I don’t even care if you went to school.” We’re always looking for that unique diamond in the rough. It goes the same with people and with companies. 

For anyone like that, it’s great that you’re reaching out like you are, but it’s got to be beyond that now. People get inundated with other things. It’s got to be a “What can I do for you?” message. That comes across really well and sets people apart. That’s what I’ve learned. 

Now I have 10 years as an investor, I can tell you this: don’t be afraid of rejection. We get rejected all the time here. Be persistent and find ways to stand out because the best ones are   doing what you’re doing too. If you can do it in a unique way and deliver immediate value, I’m going to check their email. I’m going to check that phone call and I’m going to respond. 

BRYAN WISH: The same approach that you took to get yourself into the door is almost the same approach that you take to not only find talent within Blueprint, to work with people like Francis or other self-starters, but to find the companies that you want to help further like Sunwave and other properties that you have invested into and are helping grow. 

It’s neat how that one central fuse has been embedded in you and all the things you’re a part of. That advice is applicable to anyone who wants to get into venture, growth equity, or any professional field. Your website is beautiful and something people take note of right away. 

BOBBY OCAMPO: I totally agree. We’re just looking for really unique people and unique companies. As I mentioned earlier, we’re not a venture fund. It’s very different because the companies that you’re looking at, they need you. They need money because they’re losing money and yes, it could be a fantastic return one day, but it’s not yet. They need capital to survive. 

Now, the businesses we invest in, they’re like, “Why do I need you?” It’s a very different conversation. If we can actually deliver on the things that company is short on, it really resonates with them and then they really are receptive. “I know what Blueprint can do for me. This sounds great.” We’re all trying to find platforms and entrepreneurs that align with our strategy there and not so much, “I’m going to grow, grow, grow and not think about how much money we’re losing.” It’s all about the next round and the next round after that.

BRYAN WISH: I remember Justin Lafazan, who runs Next Gen Summit, when introducing me to a potential client, said, “I’m going to introduce you to David Sherman.” He goes, “He likes to work with people who build real businesses not just do venture or startup ideas.” 

That was the first time I had ever heard these hard comparisons. It’s really interesting to look at businesses from that lens and say, “They may not need you because they are cashflow positive, but with your help, they can be even greater of a company and you’re going to help them get there.” 

I was in New York with the Morning Brew founder, Austin Rief, and we were talking about cashflow positive business models and he goes, “I like to invest in small companies who already have returns and I’m going to help them maximize it by my experienced skills and things that I bring to the table.”

I think the model you’re encroaching on and actually doing is really smart for your business. It’s very valuable to entrepreneurs who want to build something bigger than they can with the means in front of them. 

How do you do this as a company, as a person, and help the people around you do it? How do you continually reinvent yourself to stand out and do the things you’re talking about?

BOBBY OCAMPO: There are so many smarter people out there than I am. I’d be lying if I said I had some secret recipe to doing what they do that’s better than what they do. Frankly, how we try to differentiate is it starts   from the top. My co-founder and I, Sheldon Lewis, we make sure that everyone who is in at Blueprint has highly specialized roles. Since we’re not a multi-billion-dollar fund, there’s no real room for improvisation. 

What I found in venture is that there’s a lot of room for that. You can   know a little bit about a lot of things, but not a lot about one thing. That language doesn’t exist here. We try to be very good with each team member that is an expert in one or two things. Everyone has one or two roles they do here and there’s no room for improvisation or trying something or testing something out. 

We have a structure here. Some people thrive on it and others don’t. It’s almost militaristic. I don’t want to paint it in a poor light but for anyone who is looking to be an investor, the best thing someone can do when they first start is to be in a highly structured position. If you do go into a fund that’s generalist, that your jack-of-all-trades, you’re not really going to learn the trade like you should being specialized at having everyone rowing in the same direction. 

That is the key difference between venture, growth equity, and private equity. Each class has a different return profile. Looking at the firms you work with, each firm has a different strategy. The problem I found with venture is that there are no rules. Sometimes that can be great, but if you’re a young person getting into it for the first time, like I was, you’re not really getting the education that you could be getting in a more structured role. 

The best thing in the world is to have that structure early on and use what you learned to grow more as you grow over time instead of kind trying to boil a solution down at the very beginning of your career and then trying to narrow down and become an expert. 

I don’t think we’re reinventing ourselves here. Everyone seems very happy, but we know the five things we look for in a company and if that company hits those parameters, then we know it’s a fit to at least start to do our work. That is really helpful to have those roles because if those roles aren’t in place, everyone is   running around with their head cut off. That’s a terrible place to be. It’s very structured here but it can be very rewarding as long as people are highly disciplined and everyone is rowing in the same direction in the boat. 

BRYAN WISH: Structure breeds consistent results. This is something I learned from Allen Gannett, when I worked under his book launch. He’s the most structured person I know. Yet, when people met him, they’re like, “He’s so creative.” I’m like he is creative but he creates his creative during constructive periods to put his creativity into. It was very structured. That’s how I’ve adopted everything I’ve done as a system. 

For you guys, and anyone looking to stand out, and continually find that path, they need to think of the frameworks and the models that are going to allow them to be successful time in and time out.  So, where do people find you?

BOBBY OCAMPO: Our website is onblueprint.com Unfortunately, blueprint.com was almost $1 million to try to buy and not quite there yet. My email is on my website. Anyone ping me anytime. Keep grinding.