Bring ideas to life quickly. Do your research, talk to trusted advisors, and then just take the leap.
Oren is the CEO and founder of San Diego-based Flock Freight, a company working to modernize the freight industry leveraging algorithms and logistics automation to carpool freight. In this position, he leads strategy, fundraising, and executive talent recruitment as well as works closely with his team on sales development and defining the product roadmap.
Oren has been in the trucking and logistics industry for 23 years, since he founded E&H Transport Network in 1996, which he built from the ground up, including the recruitment and onboarding of over 1,000 truck drivers.
In 2001, Oren founded SolSource Logistics, a third-party logistics (3PL) company serving international Fortune 1000 clients such as Whole Foods, Wegmans Grocery, and Sprouts Market.
Where did the idea for Flock Freight come from?
The concept of pooling freight, the basis for Flock Freight, came to me rather serendipitously while I was running my previous business. While operating SolSource, where we serviced major customers like Whole Foods in coordinating logistics for mass events like store openings, we started to see patterns in the data surrounding the orders we managed. It was not uncommon for the business to handle 2 very large partial truckloads for our customers that happened to move from one transportation hub to another, like from LA to Chicago. We quickly started seeing that the financials for buying a full truck to bundle our shipments was yielding some of the highest margins in the supply chain of our business. At first it happened here and there sporadically, but soon we started recognizing a consistently profitable service that no one else on the market was offering. Thus the idea started to take shape and it became a matter of business to figure out how to bring this opportunity to scale. After careful consideration and thorough market research, it was clear that this prospect was worth chasing down – and so Flock Freight came to fruition.
What does your typical day look like and how do you make it productive?
Ok, let’s level set – there is no typical day. As an entrepreneur you can do your best to create structure to your day and how you want to spend your time, but it’s in the very nature of starting a business that every day you will be pulled in a thousand directions and that in order to succeed you need to prioritize. That said, I head into each day with some key points that set-up the day. The first thing I do each morning is refresh the numbers, check the sales, orders, and revenue for the day. This let’s me sort out how the previous day closed out and how the team is setting up to tackle the day ahead. After checking the hard data and dashboards, I’ll make the rounds with people in the office to get context to the data and better understand if there are roadblocks in the company.
The rest of the day will vary and no two days look the same. Most days are spent calibrating and resyncing with my teams. That means working with high-level teams like investors to look backward and forward for the business. Understand the runway, burn rate, and general status of the business. Then the day may pivot and I find myself coaching a green sales rep on how to close a deal. Or I’ll be working with a VP to manage a strategic initiative. I spend a lot of time talking to my teams, rolling out company wide plans, creating transparency and setting expectations.Throughout that, the day is scattered with handling recruitment, PR requests, ad hoc conversations, etc. Like I said, there’s never a dull moment for someone founding a business – but that’s what keeps it interesting.
One of the biggest things you start to crave as an entrepreneur is solo creative time. The responsibilities in the business constantly pull you away from that time in your own head that is the space where you solve for what’s next. This time is scarce, but critical to chase down because this is where you can focus on your internal mission for moving your business forward and figure out how to keep driving the change in the world you’re seeking.
Ultimately the one thing to not lose sight of at any point in time is your mission. As the leader of your business you have to constantly beat the drum. Never lose sight of the mission of the business and where the company needs to go as well as when it needs to hit that goal.
How do you bring ideas to life?
Quickly. Do your research, talk to trusted advisors, and then just take the leap. Listen to the internal queues, the formal or informal advice, and consider the external research – but ultimately you have to move on your ideas to make them more than just passing thoughts. Generally after checking these considerations and looking at the data, if I have 80% conviction on a matter then I’ll proceed. A key thing with this tactic is that you need to clearly define what success and failure look like as well as how to measure your plan against them. From there I look for proof points of something not working because it’s those signals of failure that mean it’s time for iteration. Ultimately the most important part of all of this is to understand that there is no single silver bullet; it’s all about nudging your way toward success and making those iterative steps towards progress.
What’s one trend that excites you?
Convergence of supply side connectivity in freight particularly with technologies working together, things like SaaS, apps, and APIs. This has been a dream for all of us in freight for ages. We’re not quite there yet, but we’re really on the precipice of real change. So much technology has been brought to other parts of freight, but we’re about to see it really start to impact drivers, bringing real value to them.
This industry is founded on a rolodex mentality, it was about who and how many people you know that allowed you to work well in freight. Now, the convergence of technology means more data and more insights that work on building democratized efficiency in the space. With the data and technology, there’s a reduction of the eternal dilemma where two ships pass each other in the night. Idea of data, technology achieving scale in the market, and driving connectivity is incredibly exciting!
What is one habit of yours that makes you more productive as an entrepreneur?
I rarely delay anything. I just get things done and do them quickly. Understand that you have a very particular set of talents or skills, don’t fool yourself into thinking you can be great at all things. I know I’m not good at many things, that’s why I habitually lean on others for their areas of expertise and don’t conflate their talents with my own. That’s the power of having a strong team around you. It can be easy as an entrepreneur to assume you need to be the greatest at all things if you want your business to succeed, however the greatest thing you can do is recognize what you’re good at and realize that it’s not most things. So lean into your team and trust them.
What advice would you give your younger self?
Be wary and understand how dangerous false hope can be. I’ve gotten in trouble a few times in my life when I’ve chosen to fill a role in my business because I thought it was better to be filled with someone than keep it empty and wait for the right rockstar to fill the seat with. There’s nothing scarier than seeing that empty seat daily and worrying about the implications to your organization, however don’t sacrifice quality to get security. That empty seat should keep a fire under you hunting for the right person.
I’ve tolerated low performers for too long in the past, the story I’d tell myself was that I was better with a low performer than waiting for the right performer. It’s not true. It’s false hope.
Also, I would advise people to move fast – recognize patterns quickly and act immediately. I move really fast, faster than many people are comfortable with, which can feel brutal and unkind but people like me always regret not moving faster.
Tell us something that’s true that almost nobody agrees with you on.
You can feel star talent. Most will disagree with me on this, people want data, or to give more chances, or provide improvement plans. But I can see and feel people’s sense of urgency, you can feel their eye contact. You can feel when people lean all in. I’m not sure whether reading people is an innate skill for me, or if I learned it over time in my life – but you really start to have a sixth sense for these things and hone that skill over time.
Generally, as an entrepreneur, intuition is what gives you a sense for what to dive into, then you back up and fill the story with data and research. But ultimately, you’ve got to learn to trust in yourself. People do not regret listening to their gut. The more you lean into it, the sooner, faster, and louder you’ll feel your conviction. After that, you’ve just got to act on it. This is where many struggle with integrity. Integrity is easy when it’s cheap and hard when it’s expensive, in terms of dollars, time, etc.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
I am constantly running and rerunning what I call ‘memory items’. These are the key metrics that define your business or role. For a CEO the business goals, finances, and runway are things you focus on, but there’s memory items for any role – like a sales person knowing their KPIs to track to goal. Whatever the KPIs, you need to know them like the back of your hand.
Knowing your business also means not being reliant on others to get data. You need to know how to get to the truth on your own. Why would you not want to know these numbers? They are the core metrics that drive your business.
What is one strategy that has helped you grow your business?
Product market fit and differentiation. Be perpetually obsessed with your business. Be involved in compensation planning, strategy, and market fit.
That’s when you’ve got your business going. For those entrepreneurs earlier on in the process, I cannot stress enough the importance of having a go to market strategy. So many young and eager entrepreneurs talk to me about their business ideas, but they are just that – ideas. They don’t think the business plan through. That’s where you see people separate between the ones that make things happen and the ones who just think of ideas. It’s not hard to think of a new product. The challenge is in making something a reality and creating scale. So many junior entrepreneurs don’t have a clear business strategy. I recommend you go as deep and narrow as you can with as few strategic endeavors as you can. This is how you create focus and impact. I personally aim to never have more than 3
What is one failure you had as an entrepreneur, and how did you overcome it?
False hope. Probably my single greatest failure. I’ve hung on twice in my career to people because I felt that getting less was better than getting nothing at all. But it’s better to get nothing, nothing drives more sense of urgency and there’s nothing more brutal than that empty chair. It should serve as a fire to keep moving.
What is one business idea that you’re willing to give away to our readers?
Someone should find a way to figure out what’s going on inside a trailer. We’ve got lots of tracking around the overall truck, but there’s not much visibility inside the trailer. It could probably be accomplished with a small bit of hardware and lots of brokers would pay for that data. Visibility to 1.5 million independent owner operator trucks is valuable data for a lot of parties out there.
What is the best $100 you recently spent? What and why?
I recently took my new leadership team members out for a meal. They were transitioning from a similar business where they started on the ground floor, green in their careers and participated in the massive growth of the business. Now, they’re joining my business at a similar stage but they are doing so at very different career levels. They now get the chance to direct and lead the business.
Taking time to spend casual time together to get to know one another sets the tone for this transition. And that is money well spent.
What is one piece of software or a web service that helps you be productive?
I couldn’t live without a data warehouse & the supporting data visualization tools. For my business it means Mode. With it I can, in near real-time, see key analytics for my business and that is essential.
What is the one book that you recommend our community should read and why?
Who by Geoff Smart and Randy Street is a New York Times Bestseller. It details the best practices in hiring in an informed and prescriptive manner that makes it actionable for any entrepreneur. Though the book focuses on strategy for effectively tackling hiring, the proposed methodology is really applicable beyond that. It’s about having a vision of success, then working backward from that point to today. Building milestones along the way and making them doable. So while this book is about hiring, it is very transferable to building a successful business.
What is your favorite quote?
My favorite quote is by Will Smith and it goes as follows:
“The only thing that I see that is distinctly different about me is I’m not afraid to die on a treadmill. I will not be out-worked, period. You might have more talent than me, you might be smarter than me, you might be sexier than me, you might be all of those things you got it on me in nine categories. But if we get on the treadmill together, there’s two things: You’re getting off first, or I’m going to die. It’s really that simple, right?”
I love this quote because it’s how I imagine myself as I tackle a greater purpose in this world. I’ll either win or die, but I will not give up.
- Relentlessly know your business. Full stop. No excuses.
- Running a business will be the hardest thing you ever do, accept it and seek support but do not fool yourself into thinking otherwise.
- Trust your gut and know that you are uniquely the right person to undertake this challenge. Others have entrusted you to tackle a specific challenge, so trust yourself and understand that they chose to give you their dollar, not someone else.