TLDR; How do you stay marketable (particularly in finance but also in general) as a serial entrepreneur?
After 8 years of working for myself and enjoying the fruits of entreprenuership, I lost my last company almost 2 years ago and was reduced to poverty within 6 months. It was a huge wake up call to go from $100K months to $100 in my wallet. I reinvested poorly, was too generous, and took too many risks. I was very young and made decisions I wouldn't make today, though I had a good bit of fun.
I've spend the last 12 months regaining my mental state, closely assesing my strengths and weaknesses, and deciding how to move forward.
I realized that the biggest risk of entrepreneurship is that if you fail and you don't have marketable skills or some specialized knowledge with savings, you will eventually end up broke without a ton of options. Fine at 25, not great at 30 , but bad at 40. I'm in the middle category.
You can of course build another business, but if you use all your dry powder and go bust, you better have an investor or be prepared to spend years fighting back slowly.
As for me, I realized I needed to develop skills that I was never in a position to really need as an online entrepreneur, which were mostly social skills like networking, small talk, etc while working to fill an almost decade gap of self-employment, where the only companies on my resume were ones created by yours truly. Not the best "insurance" or plan b if you need to get some scratch together with a legit 1040 gig in finance.
Now to the current situation: 30, college degree in finance, semi-broke
Last summer I was introduced to a company that buys millions in real estate tax liens each year. It's been a slow process getting my foot in the door, as they have a small team consisting of the owners who brought in people they trust. Their employed staff is probably less than 12.
After meeting one of the owners last year and getting great initial feedback (seemed impressed with me), I got nothing but crickets for 6 months after sending resumes and emails, etc. Then about four months ago they asked if I wanted to help with due diligence, accessing properties to get data for building out their financial models prior to a tax sale. It's good pay work but honestly anyone can do it and it's probably the bottom of the food chain. They're out of state and just need someone to drive the properties and make sure they aren't burnt down and assess their condition, value, occupancy, etc.
I've run this gig successfully for about 4 months now and I've been trusted to actually bid some of their sales this year. They've trusted me bidding up to 12M at one sale, and with cashier's checks up to $250K. Again, a little step up but 5 other guys they'll never hired in-house are doing the same thing.
I believe I've built a decent reputution for trust which is one of the hardest things to do with a company out of state that only a partner and CEO has met once. Luckily I'm in very close with the area manager above me, which is a very close friend of one of the owners. She's on my side and we text/chat almost daily.
The issue now is how to take this up a level, and if I have already messed up this particular opportunity.
Last month, one of the key managers called me and asked if I was still interested in doing some financial modeling for the company. I was honest in saying that most of my pursuits have been entreprenuerial since college (10 years ago) but that I've built some models personally and I'm good with numbers and my degree is in corporate finance. I belive I scared him off a little as he said, "It sounds like you're much more of an entreprenuer than anything else. How about you send me your resume and an example of a spreadsheet you've built."
He said it would take 4 key people to make a hire, so I wasn't expecting to hear back soon but it's been over a month at this point. I'm not overly concerned as I've been in this position before with them, waiting to get some feedback.
Let's say what I sent him didn't impress, as I have no work experience in financial modeling but have helped build companies up to millions in revenues and I have a good knack for numbers. I just don't see it being very difficult doing modeling for their line of business. It's not wall street. I see their bidding spreadsheets and it appears to be nothing more than risk analysis using property conditions with market and tax values and then setting the opeing and max bids to a percentage of LTV.
At the end of the day, my current gig is a 30K opportunity for 4 months a year during tax sales. With a chance to come on board for financial modeling and possibly list and sell the properties they get stuck with each year (I'm RE licensed), I can put something on my resume that will provide some added "insurance" for having a legimitate employer on my resume.
I realize this is very scattered and long-winded but I'm just looking to hear how you would turn this around and your opinions in general on entrepreneurship and how to keep yourself marketable, as most of us will untimately fail over and over (but hopefully get one big win that pays off).
I don't have any connections with analysts or anyone in financial modeling but I could teach myself (albeit not a quick solution to turn this around) at WSO with some of their tools or whatnot.
It's not easy trying to walk the line between keeping yourself marketable with a decent resume while trying to be the next millionaire entrepreneur.
What skills do you consider most valuable to keep polished?
How would you handle this?
After 8 years of working for myself and enjoying the fruits of entreprenuership, I lost my last company almost 2 years ago and was reduced to poverty within 6 months. It was a huge wake up call to go from $100K months to $100 in my wallet. I reinvested poorly, was too generous, and took too many risks. I was very young and made decisions I wouldn't make today, though I had a good bit of fun.
I've spend the last 12 months regaining my mental state, closely assesing my strengths and weaknesses, and deciding how to move forward.
I realized that the biggest risk of entrepreneurship is that if you fail and you don't have marketable skills or some specialized knowledge with savings, you will eventually end up broke without a ton of options. Fine at 25, not great at 30 , but bad at 40. I'm in the middle category.
You can of course build another business, but if you use all your dry powder and go bust, you better have an investor or be prepared to spend years fighting back slowly.
As for me, I realized I needed to develop skills that I was never in a position to really need as an online entrepreneur, which were mostly social skills like networking, small talk, etc while working to fill an almost decade gap of self-employment, where the only companies on my resume were ones created by yours truly. Not the best "insurance" or plan b if you need to get some scratch together with a legit 1040 gig in finance.
Now to the current situation: 30, college degree in finance, semi-broke
Last summer I was introduced to a company that buys millions in real estate tax liens each year. It's been a slow process getting my foot in the door, as they have a small team consisting of the owners who brought in people they trust. Their employed staff is probably less than 12.
After meeting one of the owners last year and getting great initial feedback (seemed impressed with me), I got nothing but crickets for 6 months after sending resumes and emails, etc. Then about four months ago they asked if I wanted to help with due diligence, accessing properties to get data for building out their financial models prior to a tax sale. It's good pay work but honestly anyone can do it and it's probably the bottom of the food chain. They're out of state and just need someone to drive the properties and make sure they aren't burnt down and assess their condition, value, occupancy, etc.
I've run this gig successfully for about 4 months now and I've been trusted to actually bid some of their sales this year. They've trusted me bidding up to 12M at one sale, and with cashier's checks up to $250K. Again, a little step up but 5 other guys they'll never hired in-house are doing the same thing.
I believe I've built a decent reputution for trust which is one of the hardest things to do with a company out of state that only a partner and CEO has met once. Luckily I'm in very close with the area manager above me, which is a very close friend of one of the owners. She's on my side and we text/chat almost daily.
The issue now is how to take this up a level, and if I have already messed up this particular opportunity.
Last month, one of the key managers called me and asked if I was still interested in doing some financial modeling for the company. I was honest in saying that most of my pursuits have been entreprenuerial since college (10 years ago) but that I've built some models personally and I'm good with numbers and my degree is in corporate finance. I belive I scared him off a little as he said, "It sounds like you're much more of an entreprenuer than anything else. How about you send me your resume and an example of a spreadsheet you've built."
He said it would take 4 key people to make a hire, so I wasn't expecting to hear back soon but it's been over a month at this point. I'm not overly concerned as I've been in this position before with them, waiting to get some feedback.
Let's say what I sent him didn't impress, as I have no work experience in financial modeling but have helped build companies up to millions in revenues and I have a good knack for numbers. I just don't see it being very difficult doing modeling for their line of business. It's not wall street. I see their bidding spreadsheets and it appears to be nothing more than risk analysis using property conditions with market and tax values and then setting the opeing and max bids to a percentage of LTV.
At the end of the day, my current gig is a 30K opportunity for 4 months a year during tax sales. With a chance to come on board for financial modeling and possibly list and sell the properties they get stuck with each year (I'm RE licensed), I can put something on my resume that will provide some added "insurance" for having a legimitate employer on my resume.
I realize this is very scattered and long-winded but I'm just looking to hear how you would turn this around and your opinions in general on entrepreneurship and how to keep yourself marketable, as most of us will untimately fail over and over (but hopefully get one big win that pays off).
I don't have any connections with analysts or anyone in financial modeling but I could teach myself (albeit not a quick solution to turn this around) at WSO with some of their tools or whatnot.
It's not easy trying to walk the line between keeping yourself marketable with a decent resume while trying to be the next millionaire entrepreneur.
What skills do you consider most valuable to keep polished?
How would you handle this?