Seeking Advice: Career Path in Heavy Civil Construction/Sitework

I think it's a great goal, being a business owner is a great way to build wealth.  Civil/site work is a lot of heavy machinery, and dealing with a workforce that can be sketchy and a bit rough around the edges.  It would be a lot of managing older personnel, which could be challenging in your 20's.  Also hard to win contracts with no track record, and getting the needed insurance/bonding will be challenging at first.  I think the goal of starting your own company with only 2-3 years of experience is very ambitious, but more power to you if you could make it work.  The overhead cost for that type of equipment, or even rental costs will be very large, but if you have deep pockets and manage your costs and billing efficiently, i wish you the best. 

Posting as a finance/credit professional who has had two stints as CFO of true start-up construction companies (specialty trade subcontractors). I'll give you some perspective, but feel free to PM for additional discussion or Q&A. 

First, I'll echo what @wouldbeCRE had to say in its entirety. 

Second, I'll say that in reading between the lines it almost sounds like you are pursuing this route because the skids are greased for you between having access to initial capital and a network you can leverage to get started. If that's the case; I can understand the desire and as long as it makes sense for you and you actually love it... go for it. If that's not the case and you could have access to capital to start ANY venture but just like this industry; then kudos man. Entrepreneurial spirit and America all that.

To answer your questions:

1. Is this a realistic plan?
   • If you are looking to start your own heavy civil firm doing major dirtwork for industrial/infrastructure projects with $10MM+ in contract value... then you need to plan for more than 2-3 years working for somebody else *doing that specific thing* before breaking out on your own. 
   • I don't have a specific number of years, but unless you have direct family who would be going into this business with you (and bringing their reputation, client list, and experience) or you have the capital to hire those kinds of people to lend credibility to your name; then you are right - it takes a long time to build reputation and you will need more years under your belt before striking out on your own. 
   • Heavy civil and sitework is not the kind of thing that you graduate into after starting out pushing dirt on a few residential projects and then graduating into strip centers and other commercial projects. Not to say it can't be done, but you shouldn't expect it to be that simple or easy. Prequalifications will block you out of that kind of thing and it would take many many years to build up to that. Maybe your connections can help with this, but once you start doing public projects (ports, highways, etc) even the best connections won't matter because of how procurement rules work and the contracting managers' requirement to choose the "best qualified" bid (not necessarily the cheapest). 
2. What steps to take early on?
   • Learn, learn, learn. 
     • If there is a certification or professional license you can get - get it. I understand you're coming at it from a business standpoint, but if you want to be the owner of a construction company and be successful at it, you need to be as fluent in the technical aspects of the job as any engineer or architect. This doesn't mean you need to be a professional engineer or start studying formulas for compacted soils or whatever. But you need to know exactly what it is the engineers you'd potentially employ would be doing. 
   • Take ownership
     • If you are starting out as a project manager, own every single aspect of your jobs. This means reading and carefully studying every single change to drawings no matter how minute. This will be a lot but don't shy away from it. Building that habit will save you once you are an owner/operator.
   • Become a paperwork legend
     • Construction is built first on paper so you need to learn and understand every single piece of paper that is involved in the process. From bid solicitations, RFPs, RFIs, contracts, change orders, lien waivers, and the library of AIA forms (assuming the sitework industry relies on AIA docs) you need to know them all and know what every term in them means. You cannot yet appreciate how much of the entire business turns on documentation. 
     • Whatever system you need to use to manage and own the flow of paper; create it and stick to it. You need to be the annoying person that demands all your subs send paperwork in such and such a way no later than such and such a date every month. It will save your ass at some point.
3. Advice on starting and managing risk
   • Don't be a dick. The construction industry is chock full of the absolute worst people in the world. Don't be among them. Even if it costs you a little bit... people have long memories and the industry isn't that big. 
   • Don't underestimate the amount of capital you will need. And I'm telling you right now that you probably will. 
   • Hire good people (not just talking about employees... CPAs, insurance agents, lawyers) and take their advice. Even if you think you know things they dont. Take their advice.
   • Build your back office before you earn your first $1 in revenues. Don't think you can always build it up later when you scale. Get it right early (use your CPA to help you with this) so it is scalable but don't skimp on the administrative side of your business. As a CFO, I can tell you that most construction companies do to their detriment. The ones that make it and make it big put senior people (if not close family) into the finance/admin function early on and give them carte blanche to do what is necessary.
   • Could go on and on here, either ask more questions or PM for more discussion. 

If you really want to do very well financially in this business, look up Grace Pacific in Hawaii.  
 

They own the heavy equipment for roadwork in an isolated location in the middle of the Pacific Ocean that has decent economic activity (home builders, military, city growth); they have a monopoly.  Look for markets like these where you can be the top 2 or 3 companies. 

Relationship with government (local, country, state, agencies, federal) is underrated.  Check out The Washington Campus for MBA’s (and other graduate degrees) in Washington DC to learn about lobbying.  Would benefit you immensely.  If this is what you really want to do, go to DC for that one week program.  I did it in 2015 via the Berkeley MBA.  I’m sure you can find a way in. 
 

Also, keep track of large multi decade public works projects such as rail.  They have to tear up existing roads, first find and then relocate underground utilities. Understanding all that “spaghetti” underground would be valuable for you.  Then, get to know up and coming GC’s who would win bids for these projects and be their dependable subcontractor. 

Curious if you gave any thought to majoring in construction mgmt or civil engineering?